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The Best 10 Wedding Planners in Cheshire, MA

138 Wedding Planners in Cheshire, MA

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Only In My Dreams Events

5.0

Offers 3 services
Starts at $3,000
Serves Cheshire, MA

We know that planning a wedding can be a daunting task! You’ve made the wonderful decision to declare your love in front of friends and family. Now the stress can begin. You’ll likely start asking yourself questions like: Where should we marry? What vendors do we need? Can we afford it? Who should we invite? How do we stick to a timeline? Never fear, after over 10 years of helping couples plan their dream weddings, we’re here for you. .Our wedding coordinator/planner extraordinaire Phil will be there to guide you from the start of your process until the end of your wonderful day.

“I have worked with several event planners over several years. Oskar & Mike, in my opinion, are the best in the business. They are efficient, knowledgeable, and well-organized and hire the best professionals to work with them, more importantly, they are good people. They are a dream team.”

SomeThingsFishyCatering , 3 years ago

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Nene's Deco LLC

5.0

Offers 4 services
Starts at $950
Serves Cheshire, MA

Decoration is my passion! Nene's Deco offers decorations services for all type of parties from wedding, to birthdays , baby shower, bridal showers, proposal, intimate decorations , baptism, corporate events, all milestones in your life or in the life of your business you will allow us to celebrate with you. We offer also event planning services, day of coordination, partial and full planning. We serving the Berkshires, Albany area, Springfield area , 50 miles radius from our location in Pittsfield MA. Choose your date and your theme, and we will take care of everything else. 💞

“Nene and team were amazing. Amazing. I could write an entire book on how helpful they were before and during the wedding. Nene was our Day of Coordinator and helped us stay on track throughout the entire event. We put together a backyard wedding and Nene helped us to put together an entire schedule for the day. She became the point in contact of all of our vendors, and she helped control the flow of the crowd during this event. Where Nene shines is that everything I said Nene took control of unprompted. She never needed any direction and most of the time gave us ideas we did not initially think of. We were so lucky to have Nene on our side. She made our day special.”

Chukwudi M., 2 years ago

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Katie O' Weddings & Events

5.0

Offers 7 services
Starts at $3,500
Serves Cheshire, MA

At Katie O’ Weddings & Events, our goal is to make every client sparkle. This means brighter smiles, louder laughs, and more excitement than you have ever experienced. Sparkling is about being fully immersed in the moment; it’s about being completely present, completely joyful, aware, and moved by all the positive energy and love surrounding you.

“Katie and her team worked with us over nine months to ensure the wedding of our dreams was realized. They kept us on track with all the necessary, decision timelines, recommended our vendors, and visited a number of venues with us. Every minute of the day was orchestrated by the team flawlessly. One of the best moments was when they revealed the venue to us. It was magnificent. We cannot thank them enough.”

Tracy M., 2 years ago

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Effortless Events

4.8

Offers 7 services
Starts at $1,000
Serves Cheshire, MA

Imagine walking into your wedding venue and being completely blown away by how perfectly every detail has come together. No stress, no worry - just pure joy and excitement for the celebration ahead.✨ At Effortless Events, we're dedicated to making that vision a reality. Our passion is to deliver unforgettable experiences that exceed your expectations, making your special day truly unforgettable. We believe that every wedding is more than just an event - it's a once-in-a-lifetime celebration of love, commitment, and happiness. That's why we're here to take care of every detail, from start to finish, so you can relax and enjoy every moment.

“My husband and I hired Madison as our day of coordinator. We did not hire a florist and ended up doing a lot of DIY projects for our wedding decor. We really wanted a professional to help us with setup and take-down of decor on the wedding day, so as not to burden our family/friends and take them away from the event to help. Madison was so friendly in the months leading up to the wedding and offered us lots of helpful advice on things we didn't even think to prepare for, like arranging seating charts and timing of processional songs. Our original venue coordinator ended up having to move away just a couple weeks before our wedding day, and Madison took the lead in syncing with the new venue coordinator on all the things we'd talked about. This really helped us out and took a load off our plate in those last few weeks before the wedding! The day of, she came early to the venue and, like a fairy godmother, had incorporated all of our decorations beautifully before we even arrived, so we were able to take lots of photos beforehand! Throughout the event, she cleverly found ways to repurpose some of our decor items to give them a second life, like setting reception flower arrangements along the room's bookshelves to dress them up for the ceremony, making a beautiful display with our ceremony roses and boutonnieres on our memory table, and using me and my bridesmaids' bouquets to create a beautiful sweetheart table arrangement! We were so incredibly thrilled with how well Madison and her team were able to follow our vision and exceed our expectations. A final sweet memory I have from near the end of the night - my hair was getting very tangled with my dress buttons on my back from dancing, and I was overheating and sweaty. Madison and her team arranged my hair into a beautiful low bun style so I could go back and have fun dancing again without worrying about it tangling further or looking bad. :) I'm so thankful we hired Madison as our day of coordinator, and we can't recommend her enough!!”

Mikayla, a year ago

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The Bailey Experience Wedding and Event Co

4.3

Offers 5 services
Starts at $2,500
Serves Cheshire, MA
Offer

The Bailey Experience Wedding and Event Co. is a luxury wedding planning firm specializing in refined celebrations on land and at sea. Known for calm oversight and intentional execution, we curate wedding experiences that feel composed, elevated, and thoughtfully delivered. From cruise weddings to sophisticated celebrations throughout Washington, DC, Florida, and beyond, our work is defined by discretion, clarity, and seamless direction, allowing couples to be fully present throughout their celebration.

“The Bailey Experience Wedding and Event Co. was a dream to work with for our Open House at LOFT39. Their communication style was professional, prompt, and friendly, putting us at ease throughout the planning process. The quality of their work was truly seamless - they meticulously managed load-in and schedule, ensuring the event started flawlessly. Their team's organizational skills, beautiful design work, and professional management made them a trusted, preferred planning and decor vendor for our clients at LOFT39. We would recommend The Bailey Experience over and over again for their visionary approach to weddings.”

Kendall O., 2 months ago

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Dhalia Events

5.0

Offers 6 services
Starts at $3,600
Serves Cheshire, MA

Dhalia Events is an award winning event production company & was recently named "Best Planners in the Northeast" by LuxLife Magazine. Our magic is borne out of an insistence on creating bespoke, highly personalized experiences. We focus on the uniqueness of our couples by encouraging them to be their most authentic and raw selves. We've commissioned events for large brands such as Volvo Cars and worked with top tier social media influencers to plan their events. Our team has also worked regionally and internationally producing gatherings including destination weddings & corporate retreats. Our couples book us for the following reasons:

“We absolutely loved working with Dahlia Events for our wedding. Deliece was our main point of contact, and she was truly a joy and an absolute pleasure to work with from start to finish. She took care of everything we needed, and so much more than we even knew to ask for. Deliece came prepared with spreadsheets, thoughtful questions, and clear guidance that helped us navigate decisions we didn’t even realize we needed to make, but that proved to be essential. Her organization and attention to detail made the entire planning process feel manageable and well-supported. She handled communication with all of our vendors seamlessly and always made us feel completely taken care of, no matter the detail. When a few hiccups came up along the way, she addressed them with such ease, professionalism, and genuine empathy that we never felt stressed or worried. Beyond her incredible competence, Deliece also brought the warmest, most positive energy, our calls were always something we genuinely looked forward to. And on the wedding day itself, nothing was missed (and I truly mean nothing). Everything ran so smoothly, allowing us to fully enjoy the day without a single concern. We cannot recommend Dahlia Events highly enough. Working with Deliece was one of the very best decisions we made for our wedding.”

Autumn Hamra K., a month ago

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Mills Memories

5.0

Offers 4 services
Starts at $400
Serves Cheshire, MA

Justine Mills is the founder of Mills Memories, a full-service wedding company dedicated to creating unforgettable celebrations. With a deep passion for helping couples bring their unique vision to life, Justine blends creativity, organization, and an eye for detail in every event she plans. Known for her warm approach and dedication to stress-free, seamless weddings, she works closely with each couple to craft beautiful, personalized experiences. Justine’s commitment to excellence ensures that every wedding is not only stunning but also a joyful, meaningful day for all.

“From the moment I met Justine, I knew Mills Memories was an awesome wedding planner. She listened to the very creative couple on their ideas and helped plan each one to make it happen. The information she shared with me as a fellow vendor was a blessing! It was only the details that mattered, direct, to the point, no fluff, beautifully outlined and easy to understand. You want someone like her to focus on essential information without all the unnecessary distractions. I appreciate this, as it's completely different and better than most planners I've worked with. The quality of her work and dedication is truly high-end and professional. She went with the flow and kept the entire day running smoothly. I highly recommend Mills Memories!”

Holly G., 6 months ago

Hidden gem

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Liv Charron Events

5.0

Offers 3 services
Starts at $5,000
Serves Cheshire, MA

Hi there! My name is Liv and I am a New England born event planner. Being the youngest of 12 cousins, I went to my fair share of weddings growing up. I naturally fell in love with seeing the first chapter of my friends and families life begin. I’ve worked with some of the best vendors in the Seacoast, learning and growing as much as possible. In October 2021, I took a leap of faith and opened my own business! I'll never take for granted being able to work with clients I love, doing what I love. Let’s make your dream wedding a reality!

“It is not unusual for wedding planning to begin more than a year in advance of your big day. Venue, flowers, decor, churches (bring your own priest which is a thing), engagement photos, DJ, wedding party, save the dates, invitations. The list DOES. NOT. STOP. With all of these moving parts it really makes you wonder how such a complex event can happen without the slightest issue and seemingly end before you know it. Well, Liv is our reason. After months of planning, and picking, and choosing, and changing, and scrapping ideas our bandwidth for creativity and follow-through was wearing thin. Liv saved the day. She seamlessly coordinated communications between all parties and vendors to ensure that everyone was on the same page. I will honestly say that without her our day would not have come together like it did. Everyone tells you that something will inevitably go wrong regardless of how thorough your planning. Liv didn’t let that happen. The groomsmen forgot tie clips. Liv ran 5 blocks to pick up tie clips for the boys and was back before the girls even arrived at the church. Her foresight and planning were impressive but her ability to think and adjust on the fly is what made our day go off with zero issues. We cannot thank Liv enough for her help. Do yourself a favor and let Liv take it from here. Thank you again!!!”

Kayla B., 2 years ago

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Thyme & Details

5.0

Offers 3 services
Starts at $3,500
Serves Cheshire, MA

Thyme & Details offers wedding planning and design services to sentimental couples looking for good vibes and premium personal touches. We know how important it is to be present in the moment – not worrying about organization, budgeting, managing vendors, etc. Let's make planning zesty so you can focus on your VIPs and enjoying your journey. We are based in Ohio but available for travel. Reach out so we can create something unforgettable!

“Working with Thyme & Details was a dream come true for our wedding day. Dana and her team were prompt, professional and completely focused on making our vision a reality. Their excellent work and attention to detail resulted in so many compliments from our guests. Dana and her team were prepared for everything, seamlessly collaborating with our other vendors and the venue to ensure the day went off without a hitch. As the mother of the bride, I was able to relax and enjoy the entire day without a single worry, as the Thyme & Details team took care of absolutely every detail. The bride was present, relaxed and happy the entire day thanks to their hard work. We would highly recommend this vendor to any couple planning their wedding.”

Jenni C., a year ago

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Wedding Planning Plus

5.0

Offers 7 services
Starts at $2,500
Serves Cheshire, MA

The WPP Team is unlike any other wedding planning company in Upstate New York. Composed of a core group of four event planners, including the only in-house event designer in the area, WPP is able to care for their couples and bring their visions to reality from day one until the confetti hits the floor as the celebration ends. Add to that a talented group of dedicated event coordinators and Team WPP is able to build authentic event experiences and dazzle on wedding day like no one else can.

“Wedding Planning Plus was an excellent choice for our wedding planning needs for our June 2025 wedding at the Equniox Resort in Manchester, VT. From the start, their communication style was direct, helpful, and calming, which was greatly appreciated as we planned our big day. The quality of their work and value they provided was outstanding - they were focused, supportive, and incredibly well-connected in the region, using their network of vendors to perfectly execute our wedding and beautifully and bringing our garden party tent reception vision to life. On the day of, Eliza ran the schedule effortlessly and her competence completely allowed my husband and I to be fully present. In particular, we appreciated the way that she approached us over the course of the wedding to check if we still wanted to do the next scheduled item, it gave us a sense of control over how we spent our time rather than feeling like we were manically running from task to task. So many of our friends and family have reported back that the wedding was the smoothest of the weddings they had attended this year, and its all thanks to WPP. We are so grateful for the incredible support Wedding Planning Plus provided and would highly recommend them to any couple planning their wedding.”

Lydia S., 4 months ago

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Before You Say I Do

5.0

Offers 5 services
Starts at $2,400
Serves Cheshire, MA

Hello, my lovely couples! My name is Annie and I have started my business at the beginning of 2023 and so far I've had clients from all over the East Coast. I am focused on Partial, Full time Wedding planning, Elopements and A-la carte. My goal is to help my clients and make sure that their wedding goes by the plan that they created.

“Annie is the best person for the job. She was so attentive to all the details of my wedding down to the seconds. She will fix any and all hiccups on your special day and make everything look gorgeous. I would recommend her 100% to everyone”

Shelby, 2 years ago

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Rye Street Events

5.0

Offers 3 services
Starts at $1,875
Serves Cheshire, MA

Rye Street Events was born from a deeply personal place: the joy she discovered while planning her own wedding! Inspired by the joy and creativity she found in bringing her special day to life, Caroline launched RSE with a mission: to turn each client’s unique vision into an unforgettable reality. With a strong unwavering commitment to excellence, Rye Street Events specializes in crafting one-of-a-kind experiences that leave lasting impressions. We are ready to bring your next celebration to life — and create memories you and your guests will cherish forever.

“Hiring Caroline and her incredible team at RYE Street Events was hands down one of the best decisions we made for our wedding day. From the moment we met Caroline, her calm energy, professionalism, and attention to detail immediately put us at ease. She took the time to understand our vision, our priorities, and all the little personal touches that mattered most to us. In the weeks leading up to the wedding, Caroline was a true lifesaver — organized, responsive, and three steps ahead of everyone. She coordinated with all of our vendors, created a seamless timeline, and made sure every detail was covered. On the actual wedding day, she and her team executed everything flawlessly. We had purchased a lot of decor and we trusted her to put the vision together, which she did perfectly. Because of Caroline and RYE Street Events, our day ran perfectly. We didn’t have to worry about a single thing — all we had to do was soak it all in. She handled every hiccup quietly behind the scenes and kept everything feeling calm, joyful, and completely stress-free. If you’re considering a day-of coordinator (or any level of planning help), stop searching and just hire Caroline and RYE Street Events. They are the dream team — professional, kind, and truly care about making your day perfect. We can’t thank them enough for helping make our wedding everything we hoped it would be and more!”

Anna L., 3 months ago

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The Professional Maid of Honor

5.0

Offers 4 services
Starts at $2,500
Serves Cheshire, MA

💍 The Professional Maid of Honor isn’t just a planning service—it’s your wedding day hype squad and backup bestie! Based in Boston and serving all of New England (Maine, New Hampshire, Vermont, Massachusetts, Rhode Island & Connecticut), we handle everything from dreamy invites to vendor wrangling with style, creativity, and a little extra sparkle. Whether you need full planning, partial support, or just someone to run the show on the big day, we’ve got you. Let’s ditch the stress and make your “I do” unforgettable!

“Katelynn made the planning of our wedding a pleasure. She was organized, always upbeat, has a great network, excellent ideas, yet not afraid to push back when needed. She kept the process moving along which allowed us to mostly enjoy the whole thing. She set us up for an amazing wedding, more beautiful than we could have even imagined. We loved working with her and recommend her wholeheartedly.”

Elizabeth V., 2 years ago

Simply Loved Weddings

5.0

Offers 4 services
Starts at $150
Serves Cheshire, MA

I'm Charissa owner & lead planner. My doormat says it best, 'running on coffee, wine, and the dog's time', but seriously I start every intro call with the disclaimer that you may hear the barking, snoring, or a squeaky toy in the background. I'm the twenty-something-year-old that's gone from throwing "Weddings" in her neighbor's driveway, to throwing them in some pretty amazing spaces. With over a decade of experience in weddings and corporate events, this isn't my first rodeo. Weddings are sort of my thing!

“Simply Loved Weddings was an absolute pleasure to work with for our wedding. From the moment we met Charissa, we were impressed by her calm, direct, and easygoing communication style. She truly listened to our vision and was able to elevate it through her organized, efficient, and trustworthy approach. Charissa went above and beyond, checking in with us multiple times to ensure everything was running smoothly. On the day of, we were able to simply enjoy ourselves, confident that Charissa and her team had everything under control. As far as we know, the entire event went off without a hitch, thanks to their incredible coordination and delegation skills. We cannot recommend Simply Loved Weddings highly enough!”

Anne-Levert, a year ago

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MB Events

5.0

Offers 3 services
Starts at $3,500
Serves Cheshire, MA

Here at MB Events, our number one goal has always been to have happy clients. From helping them plan at a pace that works for them, to keeping everything organized and stress free. We truly value the friendships that are made throughout the process.

“My husband, Chris, and I were fortunate enough to book with MB Events almost two years out from our wedding date of July 19, 2025. We love telling everyone that working with Marissa was the 2nd best decision we made (other than marrying each other, of course!!) Throughout the inevitable chaos of wedding planning, Marissa was our rock. She kept us on track with timelines and payments, managed communication with nearly 10 vendors at once, and helped bring our entire wedding vision to life. She truly has “the eye” — something Chris and I lack — making her guidance that much more invaluable when crafting our mood board and creating the overall design for wedding day. Her dedication, hard work and care never went unnoticed and we even had guests come up to us that night saying how amazing her team is! Every hiccup was handled with grace and professionalism, allowing our day to run as smoothly as possible (and it did!) If you choose to hire Marissa, just know you are not just hiring a planner but also gaining a friend and member of the family. Working with her over the last two years has been a blessing and more, and we owe so much of the joy we felt on wedding day to her. THANK YOU Marissa and MB events! We love you!”

Ellie M., 5 months ago

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The Traveling Tee Events

5.0

Offers 4 services
Starts at $3,500
Serves Cheshire, MA

Curating timeless memories with the beauty God gave us. Sustainably-focused, intentional design for intimate experiences. We offer full planning and design, month of coordination plus, and content creation through our Moments by The Traveling Tee Events division.

“We hired Steph as our day-of coordinator, and ended up working with her starting at 8 weeks out. She was easy to work with, and truly our wedding went as well as it did because of her expertise. She was hugely helpful in managing communication with our vendors, including a complicated venue, and helped us anticipate and plan for all the small details, like making sure we had something to eat after the ceremony, helping with the layout of the different spaces, and even providing a steamer for my dress. We put our full faith in her abilities and she totally delivered--we highly recommend her!”

Rachel, 3 years ago

Avenue Design Studio - Planning & Rentals

5.0

Offers 6 services
Starts at $250
Serves Cheshire, MA

At Avenue Design Studio, we began as a floral business, but quickly realized we could offer so much more to our clients. Over our 10+ years of working with couples on those special lifetime moments, we found ourselves stepping in to assist our brides and event clients with planning, vendor coordination, and overall event management. This inspired us to shift our focus and create Avenue Design Studio, a full-service event planning and design company. Whether you’re looking for full-service planning or just need assistance with specific aspects, we provide multiple packages and a la carte options to fit your needs. You dream it, we create it.

“Avenue Design Studio - Wedding Planning was an absolute pleasure to work with from start to finish. Their communication was always clear and responsive, which made the planning process so much smoother. When it came to the quality of their work, they truly exceeded our expectations. Our wedding coordinators and florist from Avenue Designs were incredible - they transformed the venue into a stunning, elegant space that was more beautiful than I could have imagined. My daughter showed the team what she envisioned, and Benjamin and Chad went above and beyond to bring her dreams to life. Everything about her wedding day was perfect and truly magical, thanks to the hard work and expertise of the Avenue Designs team.”

Tracey W., a year ago

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Idyllwild Event Design

5.0

Offers 3 services
Starts at $7,500
Serves Cheshire, MA

Idyllwild is an event design company for revolutionary spirits. We create laid-back and luxurious mountain love parties for New York's most passionate people. Idyllwild serves the Hudson Valley, south-central and eastern Catskills, and Western Berkshires, and functions in a hybrid online/in-person capacity. In addition to helping you plan all the visual aspects of your event, we offer floral design service, vendor and rental recommendations, sourced and custom-built decor and signage, and vintage accent furnishings. If your style is timeless as it is eclectic, rooted in Nature, beauty, and community, Idyllwild is for you!

“Working with Jasmin is a complete dream. From the moment we had our first Zoom call, almost 2 years before the wedding, I immediately adored her. She was recommended to me by our venue, Roxbury Barn and Estate, but I had already scoped her out via Instagram since she was tagged in many of the venue's photos. Her style is absolutely breath-taking and I knew I wanted to work with her right away. After our Zoom call and her shared 'vision board' and proposal, I was so excited to keep planning. She wanted to know my vision and details from the start, and welcomed allllll of the inspo pictures I sent her way! I can't emphasize enough how she truly 'sees' the vision her clients want to bring to life -- and brings her knowledge of florals and eye for design to her work with each couple. She is communicative and collaborative: she asks detailed questions to ensure you 100% love the florals in each aspect of your event. Beyond that, she is so sweet and takes the time to write detailed emails that make you feel seen and heard. Wedding planning can be a stressful process but with Jasmin's talent, professionalism, and collaboration, it feels exciting! I couldn't have been more happy with how my bouquet turned out; in fact, all of the girls and beauty vendors were gushing over the bouquets the morning of the wedding. Our floor alter, which we repurposed as florals in front of our sweetheart table at dinner, were absolutely gorgeous. As Jamin so accurately observed, I was really going for "effortless elegance" (her words, but my exact thoughts!). The gorgeous bud vases and flameless candles came together perfectly, as well as the branches I asked if she could add last-minute! From the very start, I said Jasmin was my favorite vendor to work with and I just can't recommend her enough! If you are in need of a florist in the area, book her -- it will be the best decision you make for your big day!”

Emma K., a year ago

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Events by Wei Yuh

5.0

Offers 4 services
Starts at $3,500
Serves Cheshire, MA

As an event planner with over a decade of experience, I've had the privilege of helping countless couples create unforgettable celebrations. My passion lies in crafting personalized events that reflect your unique love story. From intimate ceremonies to grand receptions, I'm dedicated to ensuring every detail is perfect.

“Wei Yuh was hired for the task of organizing a lovely and elegant Victorian Romance themed wedding rehearsal dinner at the Omni Parker Hotel on October 24, 2025. Following the dinner, a private Ghost Tour of Boston also took place for the wedding party, and the timing for these events was crucial. She did so professionally, with good communication with myself, the hotel staff, and the florist. From lace table runners to floating candles, everything was perfect when we arrived. Wei Yuh also communicated well with our guests concerning the day’s itinerary, suggestions for appropriate dress (since the ghost tour could be a bit chilly), and handled special needs requests with ease. She took charge of scheduling gift presentations and toasts between courses, tweaking them as needed to meet our schedule. I couldn't be happier with her services and I appreciate the work she put forth to make this event a very special evening!”

Nancy D., 3 months ago

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A Lively Event

5.0

Offers 4 services
Starts at $3,150
Serves Cheshire, MA

At A Lively Event, we specialize in thoughtful, detail-driven wedding planning for couples. Our focus is simple: bringing your unique wedding vision to life while building a genuine relationship with you every step of the way. We believe that planning your wedding should be just as joyful as the day itself. We prioritize communication, trust, and collaboration. Whether you’re dreaming of a romantic mountain ceremony or an elegant ballroom celebration, our team is here to guide you with expert logistics, creative solutions, and unwavering support. We handle the behind-the-scenes details so you can stay present and excited for your big day.

“From the very first phone call with Katie with A Lively Event, I knew she was meant to be in our lives. We instantly clicked. Hiring her felt less like choosing a wedding planner and more like gaining a built-in best friend who also happens to be a logistics genius and life-saving personal assistant all wrapped in one. Katie has a remarkable gift for bringing every vision together seamlessly, even when there are many voices, ideas, and passionate opinions swirling in the mix. Every detail was handled with care, every question answered before I even had to ask. If anything went sideways (and let’s be real, there’s always something), she swooped in with grace and handled it before I even realized there was an issue. I never once had to stress or lift a finger. She was our voice, our advocate, and the one person who always ensured our wishes were front and center, and truly was the key to how perfect our wedding day turned out to be. Thanks to Katie, those few precious hours of our wedding day became some of the most unforgettable memories of our lives. Her heart, her hustle, and her unwavering support made every moment perfect. We are forever grateful to have worked with her, and even more grateful that she’s now a part of our life beyond the wedding. If you want someone who will champion your love story with joy and finesse, Katie is the one.”

Jessica P., 3 months ago

Yours Truly Planning

5.0

Offers 7 services
Starts at $1,000
Serves Cheshire, MA

***CLICK ON GLOBE ICON UNDER PROFILE PHOTO TO FILL OUT WEDDING INQUIRY FORM. WE WILL ONLY RESPOND VIA BY FORM.*** If you would like us to get start on planning directly, we ask that you kindly fill out the form and one of our team members will get back to you as soon as possible!

“Wow!!! What a dream team!!! They far exceeded our expectations! No regrets whatsoever!”

James & L., a year ago

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Charity Lynn Weddings

5.0

Offers 1 service
Starts at $11,000
Serves Cheshire, MA

Through intentional design and meticulous planning, I craft a wedding experience that reflects your unique essence, infused with awe-inspiring details. Because your love story is the most extraordinary of all, I strive to create an experience that encapsulates the elements that make you special while meticulously attending to every logistical detail. Imagine a harmonious blend of beauty in the details and a spirit of epic celebration. I am passionate about creating authentic and thoughtfully designed weddings for couples who cherish their families.

“Charity was easy to work with and brought order to the chaos that wedding planning can become. She has an energetic, up beat attitude and is able to insert her positivity into tensions that can arise in the planning process. The most helpful service she offered our family was her schedule of when to do/order/decide what thing needed to be done and when from my daughter’s engagement to wedding day. She organized rehearsal night, but it still felt intimate and ended up being a very special night before the big day. We recommend her without any hesitation. Charity will love on your family as if it were her own and make the wedding process a blessing, rather than a stressor!”

Audra, 2 years ago

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The Perfect Plan

5.0

Offers 4 services
Starts at $3,500
Serves Cheshire, MA

The Perfect Plan was born from a deep-seated belief that every couple deserves to experience the joy of their engagement without the stress of wedding planning. Our founder, Connie Nye Clark, spent two decades immersed in the hospitality industry, mastering the art of event execution and building a robust network of trusted vendor relationships. She saw firsthand the difference a seamless, expertly planned event makes—not just for the guests, but for the couple themselves. We exist to guide you through every decision, big or small, ensuring your journey to "I do" is as beautiful and stress-free as the day itself.

“From the moment my husband and I booked The Perfect Plan as our wedding planners, we were impressed by their quick responsiveness and the wealth of information they provided. Connie and her team were incredibly knowledgeable, with a great attention to detail that allowed them to think ahead and ensure our special day ran smoothly from start to finish. Connie's upbeat and excited personality was a calming presence throughout the day, keeping me feeling calm and joyful. We are so grateful to The Perfect Plan for making our wedding day everything we dreamed it would be and more. Their professionalism and dedication truly made all the difference.”

Danielle, 4 months ago

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Louisa Co. Events

5.0

Offers 4 services
Starts at $1,400
Serves Cheshire, MA

At Louisa Co. Events, we create weddings that feel effortless, elegant, and deeply meaningful, blending timeless style with modern sophistication. With over 10 years of experience across New England, trusted vendor relationships, and a calm, creative approach, I ensure that every moment is beautifully orchestrated and every detail perfectly aligned.

“My husband and I had the most amazing experience working with Jamie. We only had a 3 month engagement, so it was crunch time pretty much the entire time we were planning. We hired Jamie 2 months prior to the wedding, and she made everything so stress free. Anything we asked of her, she was more than happy to do, and if she didn’t have the answer right away, she would find out and get back to us in a very timely manner. I did all the decorating myself, and Jamie had some great ideas to help me execute my day. While she kept things professional, she also felt like a friend. Her kind spirit and go getter attitude was so great to have on the day of our wedding. She handled EVERYTHING the day of the wedding and everything ran so smoothly. Everything that needed to be done the day of was in the perfect spot just where I asked her to put things, and she ran the event flawlessly. She was in contact with all my vendors and she worked out all the details with them so I wouldn’t have to which was the biggest help. My husband and I did not know what to expect going into planning, but Jamie and her team exceeded our expectations. If you are looking for someone to help you plan your wedding, I would say stop looking you have found your girl. Jamie’s assistant was also amazing and just as pleasant. I highly recommend working with Jamie and her team, and I would 100% hire her again for another event. Best experience”

Kendra, a month ago

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Daphne Ashley Events

5.0

Offers 3 services
Starts at $3,600
Serves Cheshire, MA

Born on Valentine’s Day with a lifelong love for romance, I specialize in creating authentic, thoughtfully tailored weddings that feel effortless and true to each couple 🤍 With over a decade of experience, I bring calm, creativity, and seamless organization to every celebration, ensuring your day runs beautifully from start to finish.

“Daphne Ashley Events was an absolute joy to work with for our wedding. Their communication style was efficient, direct, and kind throughout the entire planning process. As our day-of coordinators, they ensured everything ran seamlessly and kept us calm and on schedule. Their attention to detail and organizational skills were worth every cent - we could not have pulled off our special day without them. Daphne and her team went above and beyond to make our wedding vision a reality. We highly recommend Daphne Ashley Events to any couple looking for a professional, experienced wedding planning team.”

Natalee C., a year ago

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West Monroe Events

5.0

Offers 6 services
Starts at $1,500
Serves Cheshire, MA

Welcome to West Monroe Events – Your go-to for unforgettable weddings. Serving cities like Austin, Boston, and San Diego. We specialize in crafting beautiful, personalized weddings. Our expert team is dedicated to turning your dream day into a reality, handling every detail with care and precision. From intimate ceremonies to grand celebrations, we ensure your special day reflects your unique love story. Contact us today to start planning a wedding that you'll cherish forever.

“Amanda is amazing, simply put. She came out for a wedding at The Videre and seriously brought SO much good energy. It was my first time meeting her, but by how welcoming she was, it felt like I had known her forever. Not only this, she goes above and beyond for her clients. All very needed things when it comes to your wedding day! (Photos are by Brittney Welch)”

Robin Y., 10 months ago

Hidden gem

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unKAGed events

5.0

Offers 7 services
Starts at $1,400
Serves Cheshire, MA

While planning events as a side hustle for over a decade, I have also been a nonprofit event coordinator, farmer, and music festival planner. My background gives me a unique perspective on each wedding I plan. Sustainability, Inclusivity and Couple Advocacy are extremely important to me. Some fun facts: Leo with Taurus Moon and Libra Rising, ENFP, a Peacemaker, and I love a good personality quiz. I'm a sucker for fashion, and like to joke that ! can smell a good consignment/vintage shop. I had a wedding Pinterest 8 years before I even met my husband, and I will do anything in my power to give you the wedding you want.

“I don’t think I can truly explain or fit into a review how amazing Kris with unKAGed events is! We hired Kris because this was a destination wedding for us and we needed help with locating vendors and wanted to feel like we had someone that we could work with in the area that was familiar with the industry and able to coordinate day of for us. I had my initial call with Kris and immediately felt comfortable and listened to with any questions or concerns I had with planning. She offered us different vendors for catering, rentals, dj and cake. She setup up tastings and meetings with all vendors making sure we felt comfortable and confident with every vendor we went with. Kris went above and beyond being CCd on every email and on every call. She provided quick and accurate information throughout the planning process. We ran into issues with our venue along the way and Kris was right there beside us helping us and working through it. What can feel like the chaos of wedding planning we knew we could trust her and rely on her. When it came to day of as a bride it’s hard to feel like you don’t have full control over your day. However trusting Kris after working with her leading up to the big day I knew she was going to do all she could to bring my vision to life and make the best decisions for our wedding. She did just that! I can’t put into words how much she did for us - from all the work leading up, rehearsal, setting up ceremony site, setting up cocktail hour, setting up the reception tables and seating chart and then breaking it all down after - she truly does it all!! I knew I was hiring someone to help us along the way and for the day of our wedding what I didn’t know is I was hiring someone who would care about us the way she did.”

Lee-Anne D., a year ago

Hidden gem

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Lovelace Design

5.0

Offers 5 services
Starts at $7,000
Serves Cheshire, MA

NOTE: Please email us directly if interested in working together... At Lovelace Design, we believe that planning your wedding should be a journey filled with moments of joy and connection. We specialize in designing events that are both sophisticated and intentional, so that you can savor every moment of your special day. We offer comprehensive event planning services for busy professionals that don’t have the time to plan every detail leading up to their big day. Our team of experienced planners will work closely with you to ensure that your wedding is truly unique and reflective of who you are.

“We can’t imagine our wedding day and planning process without Christina—we hired her for wedding coordination and are SO glad we did! From our first conversation with her to our hugs goodbye on the wedding night, Christina was warm, fun, and professional. She kept us and our vendors organized with regular touch points over email and Zoom in the months leading up to the wedding, giving us her professional opinion on ways to make the day flow and feel the way we wanted. During our rehearsal and wedding day Christina was organized, clear, detail-oriented and friendly to everyone involved and we knew our day was in the best hands with her. We were able to be completely present and soak in every moment because Christina and her team were working in the background to keep us on time and problem solving on the fly. If there is one thing you do for your wedding, hire a coordinator—specifically, hire Christina—you’ll be glad you did!”

Sara, 3 months ago

Hidden gem

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Cathy's Elegant Events, LLC

5.0

Offers 4 services
Starts at $9,000
Serves Cheshire, MA

Cathy founded Cathy's Elegant Events in 2010. Although she was born in NYC, her family moved to the Catskill Mountains at a young age, but they maintained a home in Brooklyn. This allowed her to have a unique upbringing in both Upstate New York and Brooklyn, where many of her relatives still reside. Cathy holds a degree in Mathematics and Statistics.

“It was so fun getting to spend time with her and getting to know her during this process. Cathy made every little detail of our fairytale wedding come true. She was terrific during the planning process. When I wanted to try to handle projects myself, she stepped back and let me handle them, but was always there if I needed advice or help with anything. When I needed her to be more involved and hands on, I felt completely confident and comfortable letting her take things in the direction that she felt was best. She was always quick to answer emails and talk on the phone to hash out big picture items or last minute details. The week leading up to the wedding Cathy was AMAZING. We spent almost 2 hours on the phone making sure every last detail was taken care of and exactly the way I envisioned it. She ran our ceremony in the pouring rain and was always cheerful and positive, she was there for me for moral support all afternoon while I was getting ready, she helped setup the barn and ceremony beautifully and made sure every detail was in order. During the ceremony and reception, she made sure that my husband and I were taken care of the entire evening. Our day was absolutely perfect from start to finish and Cathy's expertise, guidance and help played such a huge part in the success of our wedding day. Thank you Cathy!! Tim and I are so grateful for all the hardwork and love you put into making our day great.”

Elise D., a year ago

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Eileen Smith Events

5.0

Offers 5 services
Serves Cheshire, MA

Her experience, creativity & knowledge in the event industry puts her ahead of most in the area. She loves creating and working with clients on all levels to make their vision become a reality. "I love getting to know my clients and enjoy becoming their "New Best Friend" prior to the event.". Her talent in design, organization, and management makes any experience working with her effortless. She makes you feel so comfortable & give you the confidence it will be an amazing event.

“Eileen was amazing as our wedding planner / month-of coordinator. Both my husband and I were SO glad we hired her. Eileen helped us make so many decisions during the planning process that led to an extremely smooth wedding day - from where the bar was located to how we processed down the aisle, from whether to do cake or a dessert bar, to when champagne was poured - she really nailed it. She also worked with all of our vendors to coordinate setup and was onsite to help make sure everything was set up correctly & as planned. Everyone jokes that something *always* goes wrong on your wedding day, no matter how much you plan, but really we had nothing go wrong thanks to Eileen! She made our day stress-free! It's also important to call out that our venue wedding coordinator quit a couple of weeks before our wedding, and Eileen stepped up and swooped in to make sure our new point of contact at the venue was fully up-to-speed. Thank god for Eileen! I highly recommend her. And if you're on the fence about needing a wedding coordinator -- just take the leap! SO SO worth it.”

Claire M., a year ago