Savor Summer at Retreat Farm’s Food Truck Roundup in Brattleboro, Vermont

Live Music. Local Food. Craft Brews. Community Vibes.

July 3 – August 21, 2025

The summer’s most anticipated outdoor gathering is back for its 8th season!

Every Thursday evening from July 3 through August 21, Retreat Farm welcomes locals and visitors alike to their popular Food Truck Roundup, a weekly celebration of live music, local flavor, and community spirit, all set against the scenic backdrop of Retreat Farm’s beautiful red barns along the West River in Brattleboro.

From 5 to 8 pm, Farmhouse Square transforms into a vibrant block party with lawn games, live performances from regional bands, a rotating selection of food trucks, and ice-cold brews from the Thirsty Goat Bar.

Whether you come to dance, dine, or just unwind, Food Truck Roundup is Brattleboro at its best.

Live Music Lineup That’ll Get You Grooving

The 2025 season kicks off on Thursday, July 3, with the foot-stomping rhythms of The Ditrani Brothers, and continues all summer long with a genre-spanning mix of bluegrass, funk, rock, Americana, and more.

You’ll hear fan favorites like Wyld Nightz, Shokazoba, and The Rear Defrosters, all performing in a lively, open-air setting that encourages dancing and connection.

Summer 2025 Lineup Highlights:

• July 3: Ditrani Brothers – This high-energy quartet fuses early jazz, Balkan beats, and gypsy swing into an electrifying performance that will kick the summer off with a bang.
• July 10: The Rear Defrosters – A Brattleboro favorite, this rotating cast of local all-stars brings a vintage country sound and infectious stage presence straight from the golden age of jukebox hits.
• July 17: Jatoba – Blending lightning-fast tempos with vocal harmonies and improvisational flair, Jatoba offers a sound that’s as danceable as it is unpredictable.
• July 24: Kendall Street Company – With a knack for crowd engagement and musical surprises, this Virginia-based ensemble will keep you on your toes with every eclectic, off-the-cuff tune.
• July 31: Wyld Nightz – This six-piece powerhouse will have you singing along and air-guitaring to every brassy anthem and feel-good classic from their expansive rock repertoire.
• August 7: Shokazoba – Award-winning and unapologetically bold, Shokazoba delivers a horn-driven dance party designed to move your feet, lift your spirit, and ignite the crowd.
• August 14: Midnight Betty – Led by the rich vocals of Chelle Martinez and Oriana Barros, Midnight Betty mixes vintage country, indie-folk, and harmony-laced pop for a set that’s soulful and sweet.
• August 21: The Miles Band – Closing out the season with groove and grit, The Miles Band brings powerhouse vocals, rich harmonies, and a brass section built to get you moving.

Food, Brews & All the Local Flavor You Crave

Sample the best of Vermont’s food truck scene with a rotating lineup of vendors offering everything from wood-fired pizza and tacos to maple-glazed doughnuts.

Wash it down with craft beer or a summery cider, then kick back with your favorite people under the open sky.

Retreat Farm’s Food Truck Roundup Ticket Info

• Advance Tickets: $5 per adult (available online starting June 1)
• At the Gate: $8 per adult (limited availability)
• Kids under 12: Free
• Season Passes: Now available! Individual, couple, and family options

As a nonprofit, Retreat Farm relies on ticket sales and community support to keep this tradition alive.

Want to make a difference? Donate to the Free Ticket Fund, which ensures that cost is never a barrier to joining the fun.

Dogs are not permitted at Food Truck Roundup events (service dogs are always welcome).

Make Brattleboro your Thursday night tradition this summer.

Bring your blanket, your appetite, and your dancing shoes, and discover why Food Truck Roundup at Retreat Farm is one of the top things to do in Brattleboro, Vermont.

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