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Food Truck Festivals in Massachusetts 2026–2027

Attend Your Favorite Food Truck Festivals in North America

Featured Events

June 13 - 14, 2026

ADifferentDrummerCraft.com

(508) 364-5551
Drummer Boy Park, Route 6A - 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.

June 14, 2026

wcna.org/festival

(781) 246-9262
Lower Common - Wakefield, MA

The festival is an annual event on the Wakefield Common, along the shoreline of picturesque Lake Quannapowitt. Craft vendors, local organizations, live entertainment, and great food comprise the day. The festival is organized by the Wakefield Center Neighborhood Association, Inc., (WCNA) as a fundraiser for its many community projects. All proceeds from all WCNA events are earmarked for our town improvement projects.

July 18 - 19, 2026

ADifferentDrummerCraft.com

(508) 364-5551
Drummer Boy Park, Route 6A - 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 1 - 2, 2026

ADifferentDrummerCraft.com

(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 8 - 9, 2026

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

Fine Arts & Fine Crafts with 75 juried artists, accompanying food, music and entertainment. In this our seventh 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. Foundation sponsored purchase incentives to encourage festival attendees will be introduced this year.

September 12 - 13, 2026

adifferentdrummercraft.com

(508) 364-5551
Drummer Boy Park, Route 6A - 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 50 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!

October 3 - 4, 2026

ADifferentDrummerCraft.com

(508) 364-5551
Drummer Boy Park, Route 6A - Brewster, MA

Juried, handmade craft-fine art show (no buy-resell, no manufactured and no reps). Great visibility on main road Route 6A in oceanside family park. Limited space per craft (5-7 vendors in one craft for balance). 10x10 spaces, tents required, easy setup with drive up spaces, Friday afternoon early setup, overnight security. Heavily advertised in print, radio, tourist publications, posters & flyers, & social media.

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Festivals with Food Trucks — upcoming

December 5 - 7, 2025

Nantucket Christmas Stroll

Downtown, Nantucket, MA

Status: Updated 5/30/2025

December 6 - 7, 2025

Winter Open Studios

Mother Brook Arts and Community Center, Dedham, MA

Status: Updated 9/8/2025

December 7, 2025

Christmas on the Common

Bridgewater Town Common, Bridgewater, MA

Status: Updated 12/2/2025

November 28 - December 28, 2025

Sowa Winter Festival

SoWa Power Station, Boston, MA

Status: Updated 8/7/2025

May 9, 2026

Watch City Steampunk Festival

Waltham Common, Waltham, MA

Status: Updated 11/18/2025