The Best Wedding DJs in Chestertown, NY

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197 Wedding Bands & DJs in Chestertown, NY

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Cascade Live Events 
Rating: 5.0 (3 reviews)
  • DJ
  • Starts at $1,750
  • Serves Chestertown, NY

We're determined to deliver our clients the highest level of production value possible. It doesn't matter how small or large your event is, we're here to make it a high-end production. We believe that quality comes from the smallest of details and we've been trained in the corporate arena to make even the smallest element of an event the greatest that it can be.

Awarded Best of Zola
If you are looking for DJs who will curate your music vibe perfectly, keep the party going all night long, and also be fun and super professional people, look no further than Cascade Live Events! Mike and Gabe were so nice and prepared for our big day. They brought music and microphones to three different locations onsite for us to have music/mics at our ceremony, cocktail hour, and reception. We sent in some guiding playlists for the reception and a pretty specific music request for our ceremony and they executed it all flawlessly (which made for the most magical recessional!). We told them we wanted to be on the dance floor with our friends all night and they seriously played hit after hit after hit! We truly only left the dance floor for bathroom breaks and drink refills. We also had the package with party lights and SERIOUSLY, it's so worth it to make your dance floor feel inviting and fun! Even our photographer and wedding coordinator complimented Mike and Gabe for being extra collaborative with them, especially when we were running a little behind schedule. Lastly, we are two brides and Mike always made us feel welcome and accepted throughout the booking/communication process and of course, the wedding day itself. We could not be happier with our choice of DJ; the rest of the wedding weekend, we, along with our friends/family, kept saying how we wished we could do it all again for another night on that dance floor! It was truly the best party of our lives, all thanks to Cascade Live Events!
Theresa B., 2 years ago
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DJSCOTTYB 
Rating: 5.0 (2 reviews)
  • DJ
  • Starts at $500
  • Serves Chestertown, NY

I’m DJSCOTTYB, the energy and heartbeat behind Bushman Sands Dream Events. I bring a smooth, crowd‑focused DJ style that keeps your event flowing from the first song to the last dance. With years of experience in weddings, parties, and special events, I know how to read a room, match the vibe, and create moments people remember.

From our first call with Bushman Sands Dream Events, we knew we had found the right DJ for our wedding. They responded to every email and text right away, answered all our questions, and made us feel heard throughout the whole planning process. On the day of our wedding, they kept the energy high with a perfect mix of songs that got everyone dancing. The sound system was clean and clear, and they read the room so well - they knew exactly when to slow things down and when to kick it up. We got so many compliments from our guests about how great the music and atmosphere were. We would absolutely book them again and highly recommend them to any couple looking for a DJ who actually cares about making their day special.
Michelle, 3 months ago
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Sweet Harmony Live Music: serving your local area nationwide! 
Rating: 5.0 (196 reviews)
·Ratings include Zola and Google reviews
  • Band or Ensemble
  • Starts at $420
  • Serves Chestertown, NY

At Sweet Harmony, we love what we do! To us, it is a beautiful thing when we are playing music that helps you to feel the special moments of your life. We've grown fast since our founding in 2008, and Sweet Harmony now serves weddings across the United States with fine local musicians. As owner and pianist, I hold certain core values that inspire my work with our customers and our relationships in the professional world: honesty, teamwork, friendliness, strength, service, efficiency, and a commitment to excellence. Our musicians typically hold advanced degrees in music and care genuinely about bringing you the beauty of live performance!

Awarded Best of Zola
The harpist and violinist were absolutely incredible — truly one of the most magical parts of our entire wedding day. My husband and I were completely in awe, and our guests couldn’t stop talking about how beautiful and cinematic the music was. It felt like something straight out of a movie, especially with the stunning ambiance of our ceremony location. From the very beginning, the process of choosing music through the company’s website was seamless. There were so many amazing song options to pick from, and we were so happy with our final selections. Hearing them come to life — especially on violin and harp — was beyond words. The musicians played so eloquently and gracefully, and their talent was unmatched. The music added a romantic, emotional, and elegant touch that elevated everything to a whole new level. Communication with the company was excellent. They were quick to respond, always friendly and accommodating, and remained professional and patient — even when unexpected weather challenges came up on the day of the wedding. They were flexible, understanding, and worked with us to make sure everything went smoothly. The quality of the performance was truly a 10 out of 10. Guests were completely blown away, and many told us how unforgettable and moving the ceremony music was. The transitions between songs were smooth and perfectly timed. I would 100% recommend this company to any couple looking to add something special to their ceremony. They are incredibly talented, professional, punctual, and just a dream to work with. We’re so grateful to have had them be part of our big day — they helped make it feel absolutely magical.
Samantha B., a year ago
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Luvdup DJs 
Rating: 5.0 (194 reviews)
·Ratings include Zola and Google reviews
  • DJ
  • Starts at $2,950
  • Serves Chestertown, NY

We are a WOMAN-OWNED and run boutique DJ Agency. We don't provide a cookie-cutter DJ service. We custom design the music to suit you and your fiance. We avoid the corny typical DJ experience so you get exactly what you want to hear at your wedding. We understand that DJing your event involves the perfect combination of bringing fun energy, choosing just the right music and being prepared. We always bring love and FUN to every event we are part of. We fully customize all the music and curate the day so it perfectly matches you.

Awarded Best of Zola
We couldn't have asked for a better DJ experience. From the moment we booked Kelton, he was extremely attentive and communicative. He helped us plan the structure of our day and musical choices. On the day of the mixing of the ceremony was seamless, even on a windy day, and his choices on the dancefloor were exactly as needed. I highly recommend this team to every couple!
Colin E., 9 months ago
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Vara DJs 
Rating: 5.0 (163 reviews)
·Ratings include Zola and Google reviews
  • DJ
  • Starts at $3,500
  • Serves Chestertown, NY

The best weddings have a feeling you can't quite put into words. The energy. The connection. The moments where everyone somehow ends up on the dance floor together. That's what we're here to create. Whether you're envisioning a DJ, our signature live band + DJ hybrid, or a fully customized entertainment experience, everything we do is tailored to create a celebration that feels like you. With thoughtful planning, and a team with taste that expertly matches yours, we'll help bring your celebration to life in a way that feels effortless. Because your wedding should never feel like someone else's. It should feel unmistakably yours.

Awarded Best of Zola
My husband and I got married 6/14/24 at Glen Sanders Mansion and Wyatt and his whole team were incredible from start to finish. From the moment we booked with them he was so responsive and helpful with the planning process. The day of everything was executed flawlessly from the entrance songs, to bridal party intros and most importantly the reception music! After a few classics for our older guests I told him to let loose and he did not disappoint! The dance floor was full all night. I got so many compliments on the party and vibe of the reception and all credit goes to Wyatt and co! 10/10 would recommend over and over again! Also the Photo Booth was a hit and it was so sweet we received a book with a copy of everyone’s Photo Booth pictures. I’ll never forget this night!
Meghan D., 2 years ago
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Direct Entertainment DJ-PHOTO-VIDEO-BOOTHS 
Rating: 4.5 (119 reviews)
·Ratings include Zola and Google reviews
  • DJ
  • Starts at $845
  • Serves Chestertown, NY

Guaranteed Compatibility... We will create what you’ve envisioned for your BIG day! Interaction/energy level Tone/vibe to match your personalities Music requests- we honor your playlist/do not play list

Awarded Best of Zola
Direct Entertainment was an absolute pleasure to work with for our wedding day. From the very beginning, they maintained constant communication with us, walking us through their detailed planning forms and extensive music database to ensure our event was customized perfectly to our preferences. On the day of, their team of professional and attentive staff listened closely to our needs, seamlessly coordinating the music, photo/video, and photo booth to keep our celebration flowing smoothly. We were thrilled with the high-quality, personalized service they provided, making our special day even more memorable. We highly recommend Direct Entertainment.
Tabitha, 2 years ago
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Supersounds Entertainment Inc. 
Rating: 5.0 (108 reviews)
·Ratings include Zola and Google reviews
  • DJ
  • Starts at $2,300
  • Serves Chestertown, NY

• 𝗗𝗝𝘀 𝘄𝗵𝗼 𝗿𝗲𝗮𝗱 𝘁𝗵𝗲 𝗿𝗼𝗼𝗺 and keep the energy on point! • Enjoy 𝘆𝗼𝘂𝗿 𝗺𝘂𝘀𝗶𝗰 𝘁𝗮𝘀𝘁𝗲𝘀 for YOUR wedding. • Sit back and relax as we 𝗰𝗼𝗼𝗿𝗱𝗶𝗻𝗮𝘁𝗲 & 𝗠𝗖 𝗮𝗹𝗹 𝘆𝗼𝘂𝗿 𝗮𝗺𝗮𝘇𝗶𝗻𝗴 𝗺𝗼𝗺𝗲𝗻𝘁𝘀 to perfection! We're so excited to bring our experience and energy to your once-in-a-lifetime celebration!!! We have been in business since 1978 (nearly double that of any Vermont Wedding DJ company) and have performed at thousands of weddings since our founding. We are the only Vermont Wedding DJ company that has videos of all our DJs! We also offer photo booths, videography, and wedding up-lighting!

Awarded Best of Zola
Before planning anything else about our wedding we already knew that the most important thing was going to be making sure it had an incredible dance floor. We had been joking during planning that a wedding was the biggest party you’ll ever throw and we wanted everyone to remember having fun dancing the night away. Matt at Supersounds made sure that that dream came true. It is clear why Supersounds was on all of our vendors’ recommended lists; they are all incredibly professional, organized, responsive, and kind. After talking with Matt we knew he would be the perfect DJ for our wedding. It was clear he was both easy going but passionate about what he does. Throughout the planning process he was able to give us advice on ceremony logistics, music, and cut together our first dance song. He helped explain what his role usually was on the wedding day and made sure that it agreed with our vision. He did an excellent job mixing the ceremony and adjusting the volumes on the microphone on the fly so that all of the audience was able to hear throughout. We had a lot of music that we knew we wanted played at the reception and cocktail hour and Matt hit all of our must plays while mixing in some extra songs that the crowd loved. The dance floor was alive the entire party and he even surprised us by sneaking in an extra final song by our favorite artist. All of our friends have told us what a great time they had at our wedding and it was in no small part thanks to Matt and Supersounds! We would absolutely hire them again and recommend them to any of our friends!
Margie H., 9 months ago
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Seductionz Soundz Entertainment & Services 
Rating: 5.0 (80 reviews)
·Ratings include Zola and Google reviews
  • DJ
  • Starts at $1,800
  • Serves Chestertown, NY

Seductionz Soundz Ent. is a full-service wedding entertainment and production company dedicated to creating unforgettable celebrations. Our mission is to provide exceptional customer service from your first inquiry to your event day, ensuring a seamless experience. With over 15 years of experience, we deliver high-quality music that keeps your guests on the dance floor. We take the time to understand your vision and bring it to life with professionalism and energy, turning your wedding into one amazing, memorable event. At Seductionz Soundz Ent., we don’t just play music, we create experiences, turning your wedding into one AMAZING event.

Awarded Best of Zola
Seductionz Soundz made my dream wedding come to life in the most beautiful and unforgettable way. From the moment we connected, Tiffany was phenomenal — her organization, calm presence, and dedication made me feel cared for every step of the way. She listened to my vision, reassured me when I had concerns, and made sure every detail was handled with love and precision. My wedding was in the garden at The Grand Marquis, outdoors during the day, and I dreamed of walking on clouds for my entrance. Because of the wind, I was told it might not be possible. But Tiffany, DJ Dave, and MC Kevin made it happen for me anyway. The moment I walked in surrounded by clouds was truly magical — like something out of a dream — and it is a memory I will cherish forever. DJ Dave and MC Kevin brought amazing energy, kept the flow perfect, and made sure every moment was seamless and full of joy. Even though it was a daytime wedding, the celebration felt full of life, excitement, and emotion. They didn’t just play music — they created an atmosphere. This team didn’t only provide entertainment — they created memories, moments, and emotions that will stay with me forever. They genuinely cared, and it showed. I would recommend Seductionz Soundz, Tiffany, DJ Dave, and MC Kevin to any bride who wants a team that delivers excellence with heart.
Sharon F., 9 months ago
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HiMotive Entertainment & Photobooth 
Rating: 4.6 (75 reviews)
·Ratings include Zola and Google reviews
  • DJ
  • Starts at $800
  • Serves Chestertown, NY

2x BEST OF ZOLA award winner! HiMotive Entertainment & PhotoBooth delivers DJ, Photobooth, Special Effect and A/V services for weddings, parties, and corporate events. We use top-tier equipment and treat every client like family. Our flexible music and event packages ensure memorable experiences, with service spanning in all states east of the Mississippi River including Louisiana—major cities like Charlotte, Atlanta, Detroit, and NYC. Book us for customized, high-energy entertainment and seamless event planning.

Awarded Best of Zola
One of the best DJ'S EVER! We used HiMotive Entertainment for our wedding and when I tell you that these people are professional, I mean it. David gave us suggestions on why certain lighting changes the whole vibe of the events. Used him for three events and all three were phenomenal. I'm talking people getting picked up on shoulders phenomenal. I still have family members messaging me a week back telling me how much they loved the DJ and MC. The MC at our reception was great as well. He got almost every single person engaged in the event and was able to get almost every person on the dance floor and no one left the dance floor. Truly a memorable experience for me, my wife, and all my guests
Dayshaun M., 3 months ago
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NATIONWIDE Wedding DJs - A Better DJ And Photographer - HAS STAFF IN YOUR AREA! 
Rating: 4.7 (51 reviews)
  • DJ
  • Starts at $499
  • Serves Chestertown, NY

Congratulations, you have the rare opportunity to have one of the best wedding teams in the country at an amazing price for your big day. We have the budget friendly packages and prices that every couple wishes they had. Elevate your wedding celebration with our award-winning DJ-MC services, trusted by over 17,000 couples nationwide for more than 27 years! Our budget-friendly packages ensure that your wedding is not only fun for all your guests, but also stress-free. We also offer stunning wedding photography and HD video services, capturing every precious moment of your special day.

Awarded Best of Zola
From their arrival and throughout our event, the team helped our wedding flow smoothly. Zach, Lana & Gabe were professional and friendly. Our guests enjoyed the music selection played by Zach. We got hundreds of photos expertly edited by Lana. Gabe made sure to capture every important moment on video. Overall we were happy with our experience and the value of our wedding package.
Zachary S., 6 months ago
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Louis Pettinelli Entertainment 
Rating: 5.0 (44 reviews)
  • Band or Ensemble
  • Starts at $3,000
  • Serves Chestertown, NY

Louis Pettinelli Entertainment is a musical entertainment company that offers an unrivaled musical experience for clients around the country. We currently service over 25 metropolitan areas throughout the lower 48, and provide musical entertainment for hundreds of events every year. Our past clients include The United Nations, Lockheed Martin, Nationwide Auto Insurance, The Shell Oil Corporation, and many more. No event is too small or large for us. Louis Pettinelli Entertainment has musical ensembles that range from a soloist to a 15 piece party band, and everything in between!

Awarded Best of Zola
We were very happy with the band we chose for our wedding. They brought great energy, played a solid mix of music that kept our guests dancing, and added a fun vibe to the night. They were also flexible which i really appreciated. They were willing to work with our unique setup, including performing on a backyard stage we built. Most importantly, they really listened to what we wanted and tailored the music to match the tone we envisioned. Their professionalism and adaptability helped everything go smoothly. We’re really glad we had them as part of our celebration and would definitely recommend them to other couples.
Emily R., a year ago
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Silver Arrow Band 
Rating: 4.9 (42 reviews)
  • Band or Ensemble
  • Starts at $2,890
  • Serves Chestertown, NY

We're live music experts, wedding enthusiasts, and party starters, infusing every event with energy and full dance floors. We're here to make your wedding the greatest party of your life! The Silver Arrows are a premium, customizable 3 to 14 piece band specializing in high-energy music–at a sensible price. Our talented and professional musicians have performed regularly with touring and recording artists including Beyoncé, Camila Cabello, Jay-Z, Justin Timberlake, Lady Gaga, Lenny Kravitz, Rihanna, Stevie Wonder, Sting, Taylor Swift, and Tony Bennett, as well as working and touring with numerous Broadway shows.

Awarded Best of Zola
Silver Arrow Band was incredible, and I highly recommend booking them! Our guests were raving about how good they were. They played a range of hits that kept all generations dancing...for the whole night. Thank you!
Jenny B., a year ago
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DJ Lennox: DJ And Photo Booth Services 
Rating: 5.0 (42 reviews)
  • DJ
  • Starts at $1,300
  • Serves Chestertown, NY

I have been Doing since 1997, with doing weddings almost exclusively since 2007. Weddings are always a great time. We go over everything with the couple and make sure their day is exactly what they are looking for.

Awarded Best of Zola
DJ Lennox provided outstanding DJ and photo booth services for our wedding. From the start, Ryan's communication was fast, clear, and friendly, which put us at ease. On the day of, he brought high energy and professionalism, delivering the party atmosphere I had requested. Ryan also took the initiative to check in with us about the music, making sure it was keeping everyone on the dance floor all night long. We couldn't have asked for a better DJ. Ryan was excellent, professional, and kind, bringing all the right vibes to make our special day unforgettable.
Danielle D., 9 months ago
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Richards Entertainment | Interactive Saxophonist 
Rating: 5.0 (41 reviews)
  • Solo performer
  • Starts at $4,000
  • Serves Chestertown, NY
  • Offer

Matthew Richards is a professional interactive saxophonist. He is the top sought after saxophonist in America. Matthew specializes in offering fun unforgettable live entertainment for Weddings. Having performed for hundreds of Weddings, client's reviews highlight Matthew's Energy, Talent, and Engagement. He is dedicated to making your vision come to life. He also values the relationship with his clients, having an amazing record in exceeding expectations. In hiring Matthew, expect your Wedding to be unforgettable! Matthew's client center approach, his passion & love for music will greatly add value to your special day!

Awarded Best of Zola
"He. is. talented. Matthew is an amazing addition to your event. We had Matt playing at our cocktail our and reception. Prior to the wedding, Matthew got on a call with us and just discussed our vision. He really wanted to know what we wanted to do with our wedding and he found ways to not take the spotlight away from us BUT TO COMPLIMENT OUR WEDDING VISION. He is a true professional who knows how to have fun. Prior to the wedding day, Matthew called us to discuss our music taste and he curated a perfect playlist for guests to enjoy during cocktail our. He works so well with the DJ and communicated with him prior to the wedding to ensure proper audio setup. Lets get to the reception. HE CAN PLAY ANYTHING. We let our DJ take the lead during the reception and Matthew was able to play along and compliment the variety of music the DJ played. He knows how to get the crowd going! The energy of the dance floor was unmatched! He played and danced with my guests and was so friendly with all the pictures. After the wedding, my wife and I had so many compliments on Matthew and how they enjoyed his saxophone playing very much. I am one extremely satisfied client of Matthew's and I promise you will be too if you have him at your event! Thanks again Matt!"
Brian & Z., a year ago
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Upbeat Occasions 
Rating: 5.0 (39 reviews)
·Ratings include Zola and Google reviews
  • DJ
  • Starts at $1,799
  • Serves Chestertown, NY

It’s the one-on-one relationship that you have with your event host throughout your planning that will, and absolutely should, spill over into the atmosphere of your event. Getting to know you with the desire to personalize your entertainment, not simply customize, is a large part of where creativity comes from, and not just mine, but yours as well! I love to offer many suggestions and ideas for your event but also find it just as important to hear your "unique" and "awesome" ideas.

From start to finish, working with Upbeat Occasions was a breeze. DJ Chris was responsive to our requests and took time to really understand what we wanted, while also reading the room and keeping the energy right all night long. His transitions were smooth and the song order kept people engaged—the dance floor didn't empty once, and I was out there dancing to nearly every track. What impressed us most was how laid back he was while staying totally in tune with what the crowd needed, and our guests wouldn't stop raving about the music selection. Chris made our reception feel effortless and fun, and honestly, it's hard to imagine our day going any better. We'd absolutely recommend Upbeat Occasions to anyone looking for a DJ who actually cares about making your wedding special.
Charlotte C., 15 days ago
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DJ Alan C 
Rating: 4.6 (39 reviews)
  • DJ
  • Serves Chestertown, NY

Over 25 Years of DJ'ing experience. Providing professional sound and lighting at reasonable costs. With an extensive library of over 200K songs providing music for all types of genres. Able to beat mix music when needed.

Awarded Best of Zola
Alan C was easy and great to work with! We had a music range from Bad Bunny, Creed, The Killers and more! We shared with him a playlist of some of our favorite songs, a list of "do not play" whether they were styles of music, artists or specific songs and a "must play" list. His online forum was easy to navigate and use. We loved the uplighting and the audio guestbook (phone)!! Also I appreciate that he read and followed through with all the small notes we left for him (specifically we asked for father/daughter, mother/son and first dance to end after the chorus and not play the entire 3-4 minutes). Such a great time. We received so many compliments on our music and the dance floor was busy all night long! He was always very responsive and quick to work with any last minute changes (we had a rainy day).
Chris & M., 10 months ago
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Cover Story Entertainment 
Rating: 5.0 (39 reviews)
·Ratings include Zola and Google reviews
  • Band or Ensemble
  • Serves Chestertown, NY
  • Offer

Cover Story Entertainment (as featured in all the leading and best publications all over New England and beyond as well as TV shows) was established by Chris Troxell, when he graduated from Berklee College of Music with a performance degree and a passion for perfection. Since the initial launch, CSE has expanded their entertainment and event services, offering clients the ease of single vendor coordination with the benefit of access to our prestigious performers, photographers, and videographers. A 12-year winner of Knot’s Best of Weddings and 13-year winner of Couples’ Choice Awards, CSE is among the BEST of NEW ENGLAND

Awarded Best of Zola
Wedding advice: hire Cover Story Entertainment! We worked with CSE for our July wedding. We went with the ceremony package, 6-piece band as well as their uplighting and photo booth services. Our experience with CSE from start to finish was 10/10. Chris and Elena are incredibly organized, communicative, and responsive. They always answered all of our questions (and I asked many!) Alec, Alex, Savannah, and the rest of the band members rocked it all night. One of the first things guests commented on about our wedding was how amazing the band was. One of our guests commented that they wish they could cancel their DJ and fly CSE to their wedding in Portugal because they loved them so much. Extremely talented musicians for an awesome price, which make a huge difference when wedding planning. When we reflect on our wedding day, Cover Story is a huge part of what made it such a memorable night. -MK AJ Dunne
MJ and A., 2 years ago
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DJ Ore Santana 
Rating: 5.0 (37 reviews)
·Ratings include Zola and Google reviews
  • DJ
  • Starts at $1,195
  • Serves Chestertown, NY
  • Offer

I’m a bilingual (English/Spanish) open-format DJ & MC who specializes in weddings for couples who want a packed dance floor and peace of mind. I make sure every guest feels included and engaged from cocktail hour through the final song. I focus on smooth transitions, natural energy, and zero cheesy mic work. I provide professional sound, immersive dance-floor lighting, uplighting, and a photo booth guests love — so you can relax and fully enjoy an unforgettable night.

Booking DJ Ore was one of the best calls we made for our wedding. From our first phone call to the last song at 1am, he was on top of everything — quick to respond, organized, and genuinely invested in getting our day right. We got married at a camp in the Catskills with the ceremony out in the woods, which meant some tricky logistics: separate sound for the ceremony in the trees, load-in with the venue staff, a timeline that kept shifting on him. Ore handled all of it and we never had to think about any of it. The music was unreal, and he kept the dance floor packed the entire night. Our guests basically refused to leave it, and we honestly lost count of how many people came up to us throughout the night to say how good the music and the DJ were. The thing I'll always remember, though, is how he made space for my Tío to play. My Tío sang and played guitar, and Ore made sure he had everything he needed to do it right. He and Chris brought so much energy and just knew how to keep the room going. If you want a DJ who's professional, easy to talk to, and cares about your day, book him. Thank you for everything, Ore — you gave us a night we won't forget. Cannot recommend enough.
Nathaniel T., 2 months ago
Groovin' You Entertainment 
Rating: 5.0 (27 reviews)
·Ratings include Zola and Google reviews
  • Band or Ensemble
  • Serves Chestertown, NY

We are Groovin' You Entertainment (GYE), your premiere destination for live music experiences that transform your events from fleeting moments to lasting impressions. GYE has been delivering excellence in the entertainment industry since 2010, curating a roster of unmatched world-class talent and expertly-crafted playlists that get everyone from 7 to 70 and beyond on the dance floor and keep them there all night.

Groovin' You Entertainment absolutely blew us away from the initial Zoom meetings to our wedding day. Their communication was clear, concise, and direct, and the quality of their work was professional, energetic, and friendly. Our guests could not stop talking about how incredible the music at our wedding was - it truly was the highlight of the night. Groovin' You kept the energy at an all-time high, and everyone was having an absolute blast on the dance floor. My husband and I, who are also musicians and attended Berklee, got up on stage to perform a song with them which was the most fun! They truly went above and beyond to make our wedding so special, and words aren't enough to thank the entire team for the unforgettable wedding we had, thanks to Groovin' You!
Nora T., 9 months ago
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The O-Tones 
Rating: 5.0 (26 reviews)
·Ratings include Zola and Google reviews
  • Band or Ensemble
  • Starts at $3,000
  • Serves Chestertown, NY

The O-Tones, a hot New England Swing and Soul band will melt your hearts and get your feet dancing. They’ve got soul. The O-Tones band has been playing for public and private events all over New England since 1990 and is a dynamic entity. Their repertoire includes many decades of music from the 1940s Swing tunes by Ella Fitzgerald and Frank Sinatra and others to Soul and Motown hits like Marvin Gaye, Aretha Franklin, The Temptations and many more! They will make your ceremony, cocktail hour, dinner and/or dancing special and unforgettable!

Awarded Best of Zola
When I heard a sample of the O-Tones music I knew immediately that we wanted this fantastic swing band. They did not disappoint! The band was extremely professional, fun and they read the crowd. From the first song they played, people in our wedding party got up and danced - how could they not? It was non-stop dancing all night long. I highly recommend the O-Tones for your wedding reception if you love swing music. And even if you don't know if you love swing music - if you are looking for a band that can get your toes tapping and get everyone out there on the dance floor - young and old - this is the band for you. I can't recommend them enough!
Marla L., a year ago
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The Barnstorm 
Rating: 5.0 (25 reviews)
  • Band or Ensemble
  • Starts at $22,500
  • Serves Chestertown, NY

The Barnstorm is an NYC-based party rock wedding band, best known for their electric and engaging dance party receptions. It's been said they're "not a real wedding band," but rather "an incredibly fun and engaging band that just happens to absolutely rock weddings!" Whether it's today's hits, top 40, hip hop, classic rock, Motown, and all things in between, The Barnstorm can do it all - putting their own spin on everything they do.

Awarded Best of Zola
We are completely obsessed with The Barnstorm! They are, without a doubt, the greatest wedding band in the world. From the very first note to the final song, they brought an energy that was absolutely unmatched. The dance floor was packed all night and our guests are still talking about them months later. They’re insanely talented, wildly fun, and just so warm and genuine. You can tell they truly love what they do and they care deeply about making the night unforgettable, not just for your guests, but for you. And not to be dramatic, but the bridezilla in me definitely came out when it came to the playlist, however the band handled it with such kindness and professionalism. They actually listened to what we wanted, learned and performed 3 or 4 songs just for us, and completely nailed them. That meant so much to us. They made us feel like total rockstars, hyped the crowd like pros, and somehow made every moment feel both epic and personal. If you’re even thinking about hiring The Barnstorm, do it. You will not find a more fun, more talented, or more genuinely caring band. We love them so much and will be forever grateful they were part of our day.
Jessica + J., a year ago
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DreSteff Events 
Rating: 5.0 (24 reviews)
·Ratings include Zola and Google reviews
  • DJ
  • Starts at $1,650
  • Serves Chestertown, NY

DreSteff Events: Music That Moves You! We believe your wedding deserves more than a playlist—it deserves a soundtrack that tells your story. Based in Montclair, NJ, we specialize in creating moments that feel as real and unforgettable as the love you’re celebrating.

Awarded Best of Zola
Stefan from DreSteff Events was great with communication - he was open, friendly and responsive throughout the planning process. On the day of the wedding, Stefan did excellent work and we had a great time! He got involved in all the wedding events and engaged really well with everyone. We played a few fun games at our reception and Stefan fit right in, joking around with the guests. Overall, Stefan and DreSteff Events helped make our special day truly memorable.
Kelly D., 2 years ago
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Larger Than Life ™️ Entertainment 
Rating: 5.0 (23 reviews)
  • DJ
  • Starts at $1,800
  • Serves Chestertown, NY
  • Offer

DJ BrianD Is Larger Than Life Entertainment, Your Versatile DJ 4 All Occasions!! 19+ Years In The Wedding, Corporate Event, & Private Party Industry & 27+ Years Spinning Wax 2 CD’s 2 MP3’s! BrianD Began His DJ Career Packing Out Bars & Clubs All Over New England. He’s Had The Honour Of Showcasing His Talents Performing At The US Open In Vail, CO, Spinning Tracks 4 Richard Simmons At A Private Event, & Volunteering At The Boys & Girls Club In Dorcester, MA, Giving The Kiddos Lessons On How 2 DJ. His Passion 4 DJ’n Transitioned 2 A Different Clientele, Although His Love 4 Entertaining Has Always Remain The Same!

Awarded Best of Zola
From the moment we first spoke with Brian, we knew we were in great hands. He’s so easy to talk to, professional, and truly on top of everything. Planning a wedding can be overwhelming, and Brian was there every step of the way—not just as our DJ, but as a calming and supportive presence. He gave us great suggestions on song choices to keep the energy upbeat and make sure all age groups felt included. When I was unsure about other vendors like hair and makeup, Brian even stepped in with thoughtful recommendations—he really goes above and beyond. On the big day, everything flowed perfectly. Brian kept the schedule on track, the energy high, and the dance floor full. We wanted the music to reflect both me and my husband’s taste, and Brian made it all come together seamlessly. We couldn’t have asked for a better DJ. He was such a big part of what made our day unforgettable. Thank you, Brian!
Kristina, a year ago
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GigRoster Band & DJ 
Rating: 4.7 (19 reviews)
·Ratings include Zola and Google reviews
  • Band or Ensemble
  • Starts at $2,500
  • Serves Chestertown, NY

The GigRoster Live Band & DJ Entertainment is a wedding band company providing musical entertainment for weddings & receptions. Our Talent Coordinator works with couples to find out about their musical tastes and vision for the big day before crafting the perfect package whether you want live music, DJ or a package of both. Our diverse musicians can play across all manner of genres and styles. From classical to funky disco classics, to smooth soul and modern pop hits, they can perform it all. Our talented group will interact with your guests and encouraging every last audience member to get involved in the celebration of your big day!

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Shawn Gillie Entertainment 
Rating: 5.0 (18 reviews)
  • DJ
  • Serves Chestertown, NY
  • Offer

Shawn Gillie has been heard on FLY 92.3, B95.5, 107.7 GNA and many other stations in the capital region. He has hosted large events and festivals and specializes in weddings. Shawn not only offers DJ services but also Audio Guestbook and Photo Booth Services as well. Reach out for pricing and packages!

Awarded Best of Zola
I’m a wedding photographer and I’ve worked with Shawn many times. He is very personable and does a great job playing music that people love and he gets people on the dance floor. When I first met him I recognized his name from the local radio station and I was a bit star struck but he is so down to earth and nice! You can’t go wrong booking him for your DJ services!
Melanie Lawrence , 3 years ago
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DJ Maxx Saint 
Rating: 5.0 (16 reviews)
  • DJ
  • Starts at $1,399
  • Serves Chestertown, NY

DJ Maxx Saint is a professional Wedding DJ serving New Jersey, New York, and Pennsylvania. Specializing in elegant, high-energy wedding receptions, DJ Maxx Saint provides live mixing, clean music, and seamless event flow from the ceremony through the final dance. Known for personalized playlists, refined crowd reading, and a modern QR-code music request system, each celebration is thoughtfully curated to reflect the couple’s vision while keeping the dance floor full all night.

Awarded Best of Zola
I've worked with DJ Maxx Saint multiple times and his professionalism and services are unmatched. As a wedding vendor, he is a dream to work with behind the scenes. He's so good at what he does and will make sure all your guests are dancing the whole night - highly reccommend!
Rebecca Loomis Photo, 2 years ago
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The Poor Cousins 
Rating: 5.0 (16 reviews)
  • Band or Ensemble
  • Starts at $500
  • Serves Chestertown, NY

Husband and wife duo, The Poor Cousins, combine intimate, nourishing songs and gutsy tunes in an easy-going style. On fiddle, Naomi finds sounds both fiery and flowing, blending seamlessly with Emmet's rhythmic and elegant guitar back-up. The duo performs various styles including classical, popular tunes, and American, Irish and all Celtic fiddle music. In addition to playing at many weddings and events in the New York City / New England area the duo have performed in many countries around the world, both together and separately.

Awarded Best of Zola
Emmet and Naomi were wonderful! They traveled to play at our wedding at Jeffers Hill Farm in Pike, NH in September 2025. They were wonderful to deal with from the initial inquiry to post wedding follow-up. They were very easy to communicate with initially and have a great repertoire of songs to choose from! They even learned some new songs that we requested for recessional/processional etc. They played a variety of beautiful songs during our ceremony and cocktail hour. They were extremely professional and wonderfully talented artists. All of our guests commented on how enjoyable they were to listen to while mingling during cocktail hour. I would highly recommend having them play at your wedding!
Kristin G., 10 months ago
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Fingerlakes Entertainment 
Rating: 5.0 (15 reviews)
  • DJ
  • Starts at $2,495
  • Serves Chestertown, NY

Fingerlakes Entertainment is DJ & MC Nathan Baker. Nathan is a modern, opnen-format Video and Music DJ that specializes in wedding entertainment. Nathan excels at DJ/MC services, and offers lighting, and photo booth services. Nathan is fun and professional and works hard to ensure couples and guests have a relaxed and memorable day. Having almost 20 years experience Nathan is a wealth of knowledge, experience, AND a FUN resource.

Awarded Best of Zola
Highly recommended. Smooth interactions in all planning, good meeting to discuss wedding music needs and great help on the actual day of the wedding reception. Nathan provided great support in an MC role. He had some very interesting/fun ways to get couples out on the dance floor. He made the day easy and successful and eventful. The dance floor was full much of the evening.
Steve D., 5 months ago