50 Fun Things to Do This Summer

From the Arts and Adventure to America’s Birthday 

Looking for amazing summer getaway ideas? Visit the Berkshires for incredible outdoor adventures, world-class arts festivals, a vibrant food scene, and plenty of colonial history. To help inspire you, we’ve put together a list of the top 50 fun things to do this summer—from awesome events to the coolest places to spend the night.

Mt. Greylock, photo by Gabrielle K. Murphy

Get Outdoors, Often

• Take a breathtaking mountain coaster ride at Jiminy Peak
• Hike dramatic boulders with a beautiful vista on BNRC’s The Boulders trail
• Go for a nature walk at Pleasant Valley Wildlife Sanctuary 
• Ride the zip lines at Catamount and Ramblewild
• Hit the mountain biking trails at Berkshire East 
• Cycle the scenic Ashuwillticook Rail Trail
• Drive the Mount Greylock auto road to the summit
• Do a day hike on the Appalachian Trail
• Rent a boat and fishing gear from Onota Boat Livery
• Learn more at berkshiresoutside.org 

Berkshire Busk! Photo credit Sam Brewer

Immerse Yourself in Arts & Culture 

• Catch a concert at Tanglewood
• Discover the magic of Jacob’s Pillow Dance Festival
• View new exhibitions at Clark Art and MASS MoCA
• See the outdoor sculpture installations at The Mount and TurnPark Art Space
• Explore a Gilded Age home and gardens at Naumkeag 
• See a toe-tapping musical at Barrington Stage or Berkshire Theatre Group
• Watch Berkshire Busk! street performers in downtown Great Barrington 
• Get inspired by plays, screenings, and concerts at Williams College
• See a film or live show at the Mahaiwe Performing Arts Center
• Visit Arrowhead, where Melville penned Moby-Dick

Tanglewood Music Festival. Photo by Hilary Scott.

Taste Berkshires: Eat, Drink, Discover Something New

• Sample the best of the Berkshires at the Tanglewood Wine and Food Festival
• Indulge in a scoop of ice cream (or three) at High Lawn Farm
• Try a new restaurant 
• Take home fresh meats and produce from local Farmer’s Markets
• Pick up the makings of a tasty picnic at Guido’s Fresh Marketplace
• Have a cold beer at Bright Ideas Brewing
• Do a tour and a tasting at Berkshire Mountain Distillers 
• Try craft ciders and iced apple wine at Furnace Brook Winery 
• Discover the premium wines produced by Balderdash Cellars
• Unwind with a local beverage and live music at Lion’s Den or Freight Yard Pub 

Huttopia Berkshires

Pick a Cool Place to Stay 

• Go glamping at Huttopia Berkshires
• Stay lakeside at Prospect Berkshires or Black Swan Inn
• Share a romantic night at a historic inn
• Book a wellness retreat at Miraval Berkshires, Canyon Ranch, or Kripalu Center For Yoga & Health
• Get a campsite in a state forest
• Surround yourself with the artsy vibe of TOURISTS WELCOME or Porches Inn at MASS MoCA
• Catch a spectacular summer sunset from Blue Vista Motor Lodge 
• Unplug off the beaten path at rustic Gedney Farm 
• Spend the night in the curated, luxury boutique inn, 33 Main
• Stay in the heart of Pittsfield’s Cultural District at Hotel on North

Pittsfield 4th of July Parade. Photo by Marina Dominguez.

Celebrate America’s 250th Birthday 

• Visit The Minute Man exhibition at Chesterwood 
• Explore Visions of a Nation at Norman Rockwell Museum
• Learn about early American life at Bidwell House 
• Hear a public reading of the Declaration of Independence at Shakespeare & Company, Norman Rockwell Museum, and Williams College
• Catch a screening of 1776 at The Adams Theater
• Learn about the 1773 Sheffield Resolves manifesto against British tyranny at Ashley House
• Trace the historic Knox Trail on a guided walk with Housatonic Heritage
• Discover the role Stockbridge Mohicans played in the Revolution at The Mission House 
• Celebrate July 3rd and 4th with James Taylor at Tanglewood 
• Attend a Fourth of July Parade. Learn more at Berkshires250