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Food Truck Festivals in Massachusetts 2026–2027

Attend Your Favorite Food Truck Festivals in North America

Featured Events

May 22 - 23, 2027

(508) 364-5551
Parker's River Landing - Yarmouth, MA

Parker's River Landing is Yarmouth's newest park. Located on Parker's River, it is surrounded by restaurants, lodging, mini golf and the Whydah Pirate Museum. A Different Drummer will be the first craft event on premise and will have 75 booths of juried crafts and foods. This busy location has constant flow of people for the variety of activities with a kayak launch, boardwalk & kid's play area. The craft fair will be arranged in the grassy area with close by parking, visible to shoppers with roadside signage, advertising in print, 'net, radio & more to promote this first time event. A second fair is also scheduled for August 21-22, 2027

June 12 - 13, 2027

(508) 364-5551
Drummer Boy Park - Brewster, MA

June A Different Drummer Craft Fair - handmade craft-fine art show (no buy-resell, manufactured or sales reps). Great visibility on main road Route 6A in oceanside family park. Limited space per craft (5-7 vendors in one category for balanced fair). 10x10 spaces, tents suggested, easy setup with drive up spaces and early setup on Friday afternoon, overnight security. Will be advertised in print, radio, tourist publications, posters and flyers, and social media./ Please see website for application & rules. Checks/money orders only Contact Pat Daley Show Director with any questions.

July 17 - 18, 2027

(508) 364-5551
Drummer Boy Park - Brewster, MA

Juried, handmade craft-fine art show (no buy-resell or manufactured, no sales reps). Great visibility on main road Route 6A in oceanside family park. Limited space per craft (5-7 vendors in one category to maintain balance). 10x10 spaces, tents suggested, easy setup with drive up spaces, Friday afternoon early setup, overnight security. Will be advertised in print, radio, tourist publications, posters and flyers, and social media.Please see website for application & rules. Checks/money orders only. Please contact Pat Daley with questions.

August 7 - 8, 2027

(774) 766-7689
Plymouth Public Library - Plymouth, MA

Fine Arts & Fine Crafts with 75 juried artists, accompanying food, music and entertainment. In this our eighth year, our Art Festival is to two days and allows both Friday night and Saturday morning set up. There will also be several family activities, and special artists demonstration exhibits. Four music performers and food trucks also participate. The popular special LEGO creation exhibit and contest is also offered. Artist awards given for top presenters in each media category. Strong marketing, and a unique artist support package.

August 7 - 8, 2027

(508) 364-5551
Drummer Boy Park - Brewster, MA

Juried, handmade craft-fine art show (no buy-resell or manufactured). Great visibility on main road Route 6A in Oceanside family park. Limited space per craft (6-7 vendors in one category for balance). 10x10 spaces, tents suggested, easy setup with drive-up spaces, Friday afternoon early setup, overnight security. Will be advertised in print, radio, tourist publications, posters and flyers, and social media. Please see website for application & rules. Checks/money orders only. Please contact Pat Daley with any questions regarding jury or sign-up.

August 21 - 22, 2027

(508) 364-5551
Parker's River Landing - Yarmouth, MA

Parker's River Landing is Yarmouth's newest park. Located on Parker's River, it is surrounded by restaurants, lodging, mini golf and the Whydah Pirate Museum. A Different Drummer will be the first craft event on premise and will have 75 booths of juried crafts and foods. This busy location has constant flow of people for the variety of activities with a kayak launch, boardwalk & kid's play area. The craft fair will be arranged in the grassy area with close by parking, visible to shoppers with roadside signage, advertising in print, 'net, radio & more to promote this first time event. The first fair is also scheduled for May 22 and 23, 2027

September 11 - 12, 2027

(508) 364-5551
Drummer Boy Park - Brewster, MA

Juried, handmade craft-fine art show (no buy-resell, no manufactured & no reps). Great visibility on main road Route 6A in oceanside family park. Balanced by craft (5-7 vendors in the same category) for 60 spaces. 10x10 spaces, tents required, easy setup with drive up spaces, Friday afternoon early setup, overnight security. Heavily advertised in print, tourist publications, posters & flyers, & social media. Please see website for application & rules. Checks/money orders only. Contact Pat Daley for jury/sign up info today!

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Festivals with Food Trucks — upcoming

November 8, 2026

Holiday Gift Show

Hanover High School, Hanover, MA

Status: Updated 9/3/2026

November 22, 2026

Holiday Artisan Fair at the Fitz

The Fitzpatrick Collaborative, Pepperell, MA

Status: Updated 9/29/2026

December 4 - 6, 2026

Nantucket Christmas Stroll

Downtown, Nantucket, MA

Status: Updated 3/25/2026

December 12, 2026

Framingham Rotary 2026 Holiday Craft Fair

Keefe Regional Technical School, Framingham, MA

Status: Updated 5/3/2026

November 20 - December 27, 2026

Sowa Winter Festival

SoWa Power Station, Boston, MA

Status: Updated 8/5/2026