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Berkshire Busk! Family-Favorite Festival Full of Music & Magic!

By Berkshires Macaroni Kid June 15, 2025

Get ready to grab your snacks, pull out your lawn chairs, and take in the sights and sounds of downtown Great Barrington—because Berkshire Busk! is back for its fifth season, and it’s bigger, bolder, and more family-friendly than ever!

From June 27 to August 30, the sidewalks come alive every Friday and Saturday night with colorful performances, upbeat music, circus fun, and a big helping of community spirit. And this year’s festival is going out with a bang—literally—with a fireworks finale on closing night! 



Something for Everyone

This isn't just music on a corner—Berkshire Busk! is a full-blown summer celebration. Expect more than 100 different performers across the season, including:

  • A 15-year-old guitar prodigy from Australia 
  • The always hilarious Wacky Chad and his pogo-stick stunts 
  • Acrobats, jugglers, dancers, brass bands, puppets, and more!
  • Plus, local faves and new surprises every weekend

Even better? It’s all free and outdoors, so kids can wiggle, dance, and giggle as much as they want.


Saturdays = Family Day Downtown

Families should definitely make a plan to hit the streets on Saturdays! Here’s what a fun-filled Saturday might look like:

10–12:30 PM – Live music at the Great Barrington Farmers Market (bring a blanket and a snack!)
1–3 PM – Stop by Robin’s Candy for balloon twisters and face painting
3–5 PM – More live music at Berkshire Mountain Distillers
6:30-9 PM – The full Busk! Magic begins with multiple stages lighting up Railroad Street


Special Events You Won’t Want to Miss

June 28 – Pride Night with Berkshire Pride

July 4 – Outdoor Screening at Giggle Park (partnered with Triplex Cinema + Boondocks Film Society!) 

August 2 – Magnificent Monster Circus with CactusHead Puppets at Mason Library

August 22 – First-ever performance by The Black Legacy Project

August 30 – Fireworks Night Finale!

Getting There is Easy

Worried about parking or getting the kids in and out? Don't stress! There’s free local transportation! More info: berkshirebusk.com/parking

  • A special Berkshire Busk! Shuttle runs between downtown Great Barrington and Sheffield during the festival
  • The BRTA Route 921 Express from Pittsfield will bring folks into town at no cost

New Stages, More Comfort

New for this year: comfy astro-turfed performance zones, professional lighting, and extra seating for families and guests who need a break. Plus, three cool new sponsor-named stages:

  • The Warrior Trading Stage – Lower Railroad Street
  • The Haddad Subaru Stage – Upper Railroad Street
  • The Berkshire Money Management Stage – Courtyard at Triplex

And don’t miss the beautiful new custom-built main stage with scenic backdrops by Oscar-nominated designer Carl Sprague!


Grab the Free Festival Guide!

Keep your family’s weekend plans easy with the Berkshire Busk! and Beyond printed guide—a colorful, 36-page booklet with performer lineups, a local dining + shopping insider’s guide, and kid-friendly picks. It’s hitting 10,000 local homes via the Berkshire Eagle, and will be available around town too!

Macaroni KID Tip: Kids LOVE giving performers a tip, so bring some small bills for them to tuck into instrument cases and tip jars—great way to support local artists and teach about giving!

Whether you're dancing with toddlers, entertaining your tween, or just looking for something magical to do on a summer night, Berkshire Busk! brings the fun. It’s local. It’s joyful. And it’s made for families just like yours.

👉 For schedules, performer highlights, and more info, visit: www.berkshirebusk.com



 This article is sponsored by Berkshire Busk! We love sharing family-friendly happenings and community fun from our partners who make the Berkshires a vibrant place to live, work, and play.