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This Weekend in the Berkshires 8/28-8/30

Late Summer in the Berkshires: Fairs, Foliage Prep & Mountain Adventures

Summer is winding down, which means crisp air and gorgeous fall colors are just around the corner. From classic country fairs and open-air concerts to stunning hikes and local dining, grab your group and plan your next Berkshire escape. 

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Special Events & Entertainment:

  • All Weekend: Head over to the classic Cummington Fair for agricultural fun, rides, and local exhibits (pair it with our hike of the week!).
  • Friday (08/28): Check out The Mount Ghost Tour or catch the It’s a Riot reception at the New Marlborough Meeting House.
  • Saturday (08/29): Experience morning Goat Yoga at Hancock Shaker Village or take a Norman Rockwell Walking Tour in Stockbridge.
  • Sunday (08/30): Enjoy Museum Day at the Berkshire Museum or catch the Olga Dunn Dance Company at The Mount.

🎭 Theater:

The region's iconic stages are keeping the energy high as summer closes out. Be sure to grab tickets for:

  • Lucia di Lammermoor Opera at The Mahaiwe (Friday)
  • Hubbard Street Dance, Chicago at Jacob’s Pillow
  • Noises Off at Barrington Stage Company
  • Hamlet at Shakespeare & Company
  • Unicorn Love Song at the Unicorn Theatre
  • Yellow Wallpaper at Great Barrington Public Theater

 🎨Art & Gallery Exhibits:

Explore local galleries and exhibits:

  • Art in the Berkshires Gallery: "The Line of It All" (All Weekend)
  • The Wit: “Cool Baby Baby” by Tom Marosz (All Weekend)
  • Ozzie’s Glass Gallery: Hand-crafted glass pieces (All Weekend)
  • Eastover Contemporary Art: "Listening to Thunder" (All Weekend)
  • Bernay Fine Art: Summertime exhibit (All Weekend)
  • Follow @artintheberkshires for all upcoming art events!

🛍️Shopping in Stockbridge:

Discover unique local finds while wandering through our charming towns:

  • Peace, Love and Chocolate for artisan sweets, BerkCHEERS specialty boutique, and Shop Around the Corner for upscale souvenirs.
  • Take a break and have some coffee and a patisserie from Lost Lamb (and do a little people watching)
  • Sidetracks for unique treasures, Whispered in the Heart for local artisan gifts, and Nejaime’s Wine Cellar (which usually has some fun tastings going on!).

🍴 Good Food & Dining

Working up an appetite? Our local food scene has incredible options for every craving:

  • Lee (Walkable from BHS):
    • Agave’s Mexican: Delicious food and such a nice team!
    • Station Gastropub: Great atmosphere for a nice dinner at the bar.
    • Keep it JuJu’s: Pizza, gyros, and soft serve!
  • Stockbridge: Once Upon a Table for a refreshed, intimate bistro experience.
  • Lenox: Pizzeria Boema for wood-fired pizza and Frankies set up for the ultimate summer vibes.
  • Great Barrington: Ask for the special at Steam Noodles or grab a bite at The Bistro Box, a fun, tasty outdoor burger shack!

🎸 Live Music

While visitors flock to Tanglewood, the local music scene thrives across the entire county all weekend long:

  • Friday (08/28): Barrington Hall featuring Little Lies (Fleetwood Mac tribute).
  • Saturday (08/29):
    • The Guthrie Center with Tom Rush.
    • Balderdash Cellars with Wanda Houston.
    • Buttonball Barn with The BTU’s.
    • Tanglewood Open Rehearsal.
    • The Stationary Factory featuring Rory Block.
  • Sunday (08/23): 
    • Michael Junkins & Friends at The Lion’s Den (a local favorite).

🥾Hike of the Week: Dry Hill Reservation - New Marlborough

Bear Swamp (The Trustees): A landscape of hard beauty: fields reclaimed by forest, and dark lowlands illuminated by colorful wildflowers in bloom. (Plan the Cummington Fair for the same day!)

  • 🥾 Ease: Follow three miles of trail—steep in places—to widely varying landscapes.
  • 🗺️ Length: A three-mile trail network featuring a mix of rugged lowlands and varying elevations.
  • Sites: Including the aptly named Fern Glade Trail passing through carpets of ferns and wildflowers, the Beaver Brook Trail stumbling upon an aging stone dam supporting a beaver dam, and the Lookout Trail ending at a grand vista of apple orchards and the Green Mountains.
  • 📍 Location: Ashfield, MA, offering diverse terrain and excellent trail exploring.

🧗 Outdoor Adventures

Only a few more weeks left for our summer playgrounds:

  • Catamount: Hit the "Catamonster" zip line and one of the largest aerial adventure parks in the country (we had a blast here last week!).
  • Jiminy Peak: Ride the legendary alpine coaster, mountain coaster, and scenic chairlift rides.
  • Ramblewild: Explore a massive tree-to-tree aerial park hidden deep in the forest canopy.
  • Berkshire East: Ride the Thunderbolt Mountain Coaster or hit the world-class bike park.

🎟️ Berkshires Travel Tip: The final summer performance tickets are moving incredibly fast. Secure your spot early for venues like Jacob's Pillow, Tanglewood, and Shakespeare & Company.

Explore more insider favorites on the Berkshire Blog

Planning your visit? Berkshire House Stay is located close to it all. Staying with us means everything is within 15 minutes, making your trip even more seamless. Click here to check availability: BHS Availability

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