The Best Wedding Caterers in Rupert, VT

TRAIL BREAK launched 8+ years ago and we were lucky to quickly find our schedule FULL during those first few years (and every season since) due to our casual yet professional approach to this business! We are a crew that clearly has fun at events (we'd have to given that we roll up with a giant, bright, plaid-wrapped trailer). We are an LGBTQ-friendly company that focuses on providing the highest VALUE for ALL of our clients.

Based in Brattleboro, Vermont, our restaurant and catering services are driven by the ingredients we source locally -- from our meats and cheeses to our vegetables and honey -- from farms and gardens around the region. Our chef-driven menus feature fresh, seasonal ingredients served in classic American cuisine and inspiring international fare.

PR Bartending & Waitstaff offers a fully insured, award-winning mobile bartending and waitstaff service that specializes in rustic barn and tented weddings, as well as corporate and private functions across New Hampshire, Maine, Massachusetts, and Vermont.

It's your story. Let us help you write it... Your wedding day deserves to be extraordinary, and we’re here to make that happen! Trust us to provide deliciously crafted food and exceptional hospitality that will have your guests wanting to dance the night away. Let’s create an unforgettable celebration that everyone will talk about for years to come — complete with memorable moments and amazing dance moves! With over 15 years of expertise in the events industry, our dedicated team is passionate about delivering exceptional culinary artistry and creating extraordinary atmospheres for every occasion.

With over 15 years of experience Maison D is the premier catering and hospitality company you would ever need. We do everything from catering to event planning and everything in-between. We take your event to the next level and elevate it in every way possible

Big Hollow Kitchen is a Vermont pop-up caterer serving fresh, made-to-order breakfast sandwiches cooked on-site. We specialize in wedding weekend breakfasts, bridal party meals, and post-wedding brunches.

Glad Mouf BBQ – Unforgettable Flavor for Your Special Day At Glad Mouf BBQ, we believe every wedding deserves unforgettable food that brings people together. We specialize in craft barbecue with a gourmet twist, featuring the world’s most tender smoked oxtails, melt-in-your-mouth brisket, juicy smoked chicken, brisket tacos —all paired with our legendary sauces. We offer catering with a choice of station-style service with pre-portioned servings or a buffet. Enjoy a special rate of $50 per person for 100+ guests or $75 per person with a 50-guest minimum. Our customizable menu allows you to create the perfect meal for your wedding vision.

Deet’s Catering brings over 80 years of family heritage to your wedding day, ensuring your celebration is built around incredible food and shared experiences. As a premier full-service caterer in the Capital Region, we specialize in on-site cooking, transforming your venue into a live kitchen where guests enjoy the aromas of fresh, gourmet meals prepared just for them. From rustic barn weddings to elegant plated dinners, our team handles every detail—from champagne pouring to cake cutting—with professional care. Whether you desire interactive pasta stations or our signature grilled NY Strip steaks, we treat your guests like family.

John passion is to serve the most flavorful and gourmet barbecue possible. His vast barbecue menu and ability to adapt to his client needs is unsurpassed. Tailgate Gourmet Catering remains one of Massachusetts, Rhode Island and New Hampshire’s leading caterers, applauded for both its gracious service and mouthwatering take on barbecue.

Gunnar’s Icelandic Hot Dogs is here to bring something different—and a lot delicious—to your wedding day! We’ve put our own twist on Icelandic-style hot dogs that have guests raving about being the best they’ve ever had. While our traditional menu is designed to please, we’re happy to collaborate with you on any custom options or unique menu items that’ll make your day truly special (caviar dogs, anyone?). Whether it’s a fun rehearsal dinner, a late-night snack to fuel the dance floor, or a memorable surprise that’ll have your guests talking, we’re here to add that chef’s kiss to your celebration!

At Best of Both Worlds Cuisine, we bring elevated Caribbean fusion to modern weddings, blending Haitian and Jamaican heritage with refined technique and contemporary presentation. Rooted in authenticity and crafted with high-quality ingredients, our cuisine celebrates bold island flavors while honoring the sophistication of today’s wedding experience. With years of event expertise, we approach each celebration with precision, creativity, and a deep respect for the significance of your day.

Hi! We are Cassie & Taylor, owners of Boards And Bites. Our love for charcuterie, event planning, creativity, and our beautiful friendship, naturally led us to create Boards And Bites. We craft beautifully handmade charcuterie grazing tables, grazing tables + bites, charcuterie cups, and even dessert tables! Our services are entirely customizable, allowing us to perfectly tailor every detail to the individual desires, themes, and personal style of each couple on their special day.

Transport your guests to the Alps with Ben's Raclette! Since 2023, Ben Piscopo has specialized in serving crispy, gooey Alpine cheese scraped onto fresh baguette and potatoes with seasonal accompaniments right in front of guests.

As a Michelin-trained chef, my business is built on shattering the expectation of standard "wedding food" by delivering an elevated, high-end restaurant experience. Backed by an elite team—including a meticulous sous chef, an expert pastry chef, and professional servers—we handle every moving part with absolute precision. We believe high-volume events should never compromise on quality. From premium ingredients to flawless execution, my team handles every detail so you can enjoy your day. For us, food is the heartbeat of an unforgettable wedding, and we are here to make yours spectacular.

*GUEST COUNT MAX 50 PEOPLE. * The Rooted Anchor offers personal chef catering services, using only local and sustainable ingredients. With over 15 years of experience, we pride ourselves on providing a memorable experience that highlights sustainability. *PLEASE NOTE*: $500 minimum for small parties/apps only! All other menus are priced at $65-$100+ per person.

** WE ARE NOT ACTIVE ON ZOLA, FACEBOOK FOR PRICING & INQUIRY *** Lakota BBQ is a wedding catering service located in Rensselaer County, NY. This catering service is a family-owned and operated business that has been in operation for over a decade. These culinary experts are excited to help you add a delectable and personal touch to your wedding spread.

Starting in 2014, Holyoke Hummus Company is a food truck and catering company serving falafel, hummus and other Middle Eastern treats. We have several options to take the hassle out of event planning. Hire The Great Garbanzo. Your guests will love ordering their food from the truck! It adds a fun dimension to your gathering. We can bring the food to you and provide catering platters.

Tuck-ins are a roastable, Inside-Out S’more on a stick, each containing a crunchy handmade graham cracker, covered in decadent chocolate, all inside a fluffy marshmallow! Tuck-ins® are available in Classic, Cookies & Cream, and Peanut Butter! Tuck-ins can be given out as favors with guests roasting them at home over a gas or electric stove. You can even have your own roasting station at your event with TerraFlame Fire Bowls available through Tuck-ins!

Established in 2017, we started as a distillery and then expanded to include a restaurant and catering services. St. Johnsbury Distillery spirits are distilled right in our facility in beautiful St. Johnsbury, so our bar services are a uniquely Vermont experience. Our president and co-founder is also our amazing head chef and he has spent years crafting a delicious menu that includes some important wedding staples, as well as some unique recipes too. Our restaurant and tasting room serves as a great location for rehearsal dinners, showers, and more intimate weddings too!