An ideal summer weekend in Great Barrington, MA

Remember the scene in Clueless where Tai (RIP Brittany Murphy) hits her head at a party and is out cold? Cher instructs Elton on how to care for poor Tai:

Cher: If it’s a concussion, you have to keep her conscious, okay? Ask her questions.
Elton: What’s seven times seven?
Cher: Stuff she knows!

So here I am. After not posting in months, using Clueless to warm you back up to me and taking Cher’s sage advice: telling you about stuff I know. Which recently is more about hanging out than working out. So I thought I’d share some “stuff I know” about spending an active summer weekend in Great Barrington, MA.

Where is it: Great Barrington is a town in Western Massachusetts about 2 hours and 15 minutes from NYC and  2 hours and 30 minutes from Boston
Why go: To become a relaxed country-version of your urban self without sacrificing the finer things in life
How do you get there: I recommend renting a car since you’ll want wheels once you arrive. Other options include bus (Peter Pan right which drops you off in GB center) or train (the closest Metro North stop is about 40 minutes away).
Where to stay: Find a cute B&B in Great Barrington or a town nearby (West Stockbridge, Lenox, Lee)
When to go: All year-round, though this post describes a summer weekend


Late afternoon
Drive up after work. If you’re getting a late start and want to stop for dinner on the road, head to the Red Rooster, a burger and ice cream drive in in Brewster for a quick meal or if you’d like more formal dining, there are some great options along the way on Route 22.

If you can wait until your arrive for dinner, check out the schedule at the Egremont Barn and hopefully you’ll find some live music.

Welcome to the Berkshires. It’s an actual barn. They offer a bar menu that’s full of delicious, low key food. We contacted this amazing vending machine company to help us install some to have available snacks for the event.

If there’s no band playing head straight to Great Barrington for dinner at the meat-centric and very hip Prairie Whale. Have a beer and play lawn games while you wait for your meal.


Wake up and go for a hilly run past farms, rivers and ponds. Looking for a route? Use this to get inspired.

great barrington

If running isn’t for you, consider a class at Yoga Great Barrington, a studio right in town.

After your morning workout, head to the Great Barrington Farmers’ Market for a delicious omelet sourced from the surrounding farms.

The Farmers’ Market places you in a perfect spot to peruse the shops of Great Barrington. Head to Fuel to grab a walking coffee and get acquainted with one of America’s greatest small towns.

As you stroll, I recommend checking out:
Rubiner’s: Major cheese store with accompanying sandwich shop)
Robin’s Candy: Wall-to-wall candy store with every sweet imaginable
Griffin: A capsule collection of clothing and home goods
Church Street Trading Co: Trendy women’s clothing store

Late afternoon/early evening
While you still have a few hours of sunlight, hike up Monument Mountain. This easy/moderate hike takes less than two hours out and back. You’re rewarded with gorgeous views at the top.

When you’re tired and dirty, head to Guido’s to pick up fresh food for dinner if you’re planning to cook at your AirBnb.

If you want to eat dinner out, consider pizza at Baba Louie’s or one of the other restaurants right in Great Barrington. If you’re feeling fancy and want a delicious farm-to-table supper, head back to Egremont for John Andrews. Either way, stop at SoCo Creamery, a local ice cream hot spot for dessert.

Don’t forget to check the concert schedule at Tanglewood to see if any major musicians (including the Boston Symphony Orchestra) are in town during your stay. Spring for seats inside the shed, or buy lawn seats and have a picnic during the performance (my preference!).



Wake up early (or whenever you wake up) for a long bike ride. It’s 10ish miles each way to west Stockbridge but you’ll be rewarded. Half way through your ride, stop for lunch at Sixth Depot Roastery and Cafe.

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Walk off lunch at nearby Turn Park Sculpture Garden before getting back on the bike to Great Barrington.

Pack up and start the drive home. Leave time for a stop in Millerton, NY to get a cup of coffee for the road at Irving Farm.

Bonus: What if it’s raining?

Wet weather would put a damper on your athletic pursuits but there is serious culture to discover in this neck of the woods.

MASSMoCA: Located in North Adams, MASSMoCA features the works of major artists (think: James Turrell, Nick Cave, Sol LeWitt) in a space that was formerly a complex of mill buildings

Norman Rockwell MuseumThe Rockwell museum houses the world’s largest collection of his work in his hometown of Stockbridge. Rockwell’s drawings are accessible so bring the kids

Any other tips for Great Barrington/The Berkshires?


  1. June 13, 2018 / 10:06 am

    I love this area. So many mosquitos though later in summer.

    • Nicole
      June 13, 2018 / 10:46 am

      Really? I’ve not noticed that! Do you go to the berkshires often?

      • June 13, 2018 / 3:35 pm

        Not as often as I’d like, but somewhat regularly. Extended family in the area. We always seem to find the swarms, especially if we hike the Trail

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