12 Reasons we love Great Barrington

We’ll keep it simple: We love Great Barrington. It’s one of, if not our favorite, town in the Berkshires and is a must-visit for anyone visiting the region. We pulled together our favorite things to do in Great Barrington to help you with your next trip.

The Berkshires are a dreamy destination to visit no matter the season – whether shopping, eating, drinking, hiking, seeing a show, cross-country skiing, cooling off in a lake, or enjoying any of the many other activities that the charming little town has to offer.

Where is Great Barrington, MA 

Great Barrington is a 45-square-mile region in the Berkshires in Western Massachusetts. It’s in what locals refer to as “South County” and borders West Stockbridge, Stockbridge, Lee, and Alford to the north, Monterey to the east, New Marlborough, Sheffield, and Egremont to the South. 

Great Barrington is about 30 minutes to Pittsfield, 55 minutes to Albany, 40 minutes to Hudson, 75 minutes to Hartford, and about 3 hours to New York and Boston. 

Perhaps most importantly (if we do say so!), is that Great Barrington is only 11 minutes from Oak Hill House, our cozy Airbnb cottage in New Marlborough. 

History of Great Barrington, MA

where is great barrington ma

Mohican Indians traveled along the Hudson River into the Housatonic valley and settled in what we now know as Great Barrington. The area was originally known as Mahaiwe, meaning the place downstream,

Officially incorporated in 1761, Named after Lord Barrington, an English aristocrat, Great Barrington was a center of government and commerce during the 1700s. 

The Berkshire Railway grew and helped the town become a major center of trade for the region. Over the years, fires devastated the town and changed the landscape, especially in the 1800s. 

Nowadays, Great Barrington is a bustling cultural hub – particularly along Railroad Street – with charming shops, great food, and lively events. 

To experience the history in real life, be sure to check out the town’s historical walking tour.

Our favorite things to do in Great Barrington

Best things to do in Great Barrington MA
Railroad Street – Great Barrington Photograph by Geoffrey Coelho – Fine Art America

Downtown Great Barrington is a perfect place to spend your day window shopping, pop by to grab some groceries or a bite to eat, or warm up with some hot chocolate or cool down with an Aperol Spritz, depending on the season! 

Because Great Barrington is less than 15 minutes from Oak Hill House, we tend to spend most of our time there and love to share recommendations of our favorite things to do in Great Barrington:

1. Go shopping

Downtown Great Barrington is a charming center in the Berkshires, and one of our favorite places to spend time in the region. The core of downtown is along Main Street and wraps around Railroad Street. In recent years, Bridge street has also added a few new shops, including Hammertown, which has beautiful furniture and home goods.

You can easily spend a few hours browsing the myriad of shops downtown. To take home a piece of the Berkshires, pop into Happy Place Berkshires, where you can grab some local touristy (but cute!) apparel.

Barrington Outfitters and Westerlind both have outdoorsy gear and are great shops to pick up something for a hike, skiing, or kayaking, depending on the season. There are about a dozen other boutiques with everything ranging from clothing to home goods to bookstores and crystal stores.

If you’re done walking around and looking to do some more shopping, travel along route 7 and you’ll find about a dozen antique stores within a 20 minutes drive of Great Barrington.  

2. Eat delicious food

View this post on Instagram

A post shared by Prairie Whale (@prairiewhalegb)

It’s probably clear by now that we love everything in downtown Great Barrington, but one of our favorite parts about the town is the delicious food options. 

Great Barrington restaurants are often considered some of the best restaurants in the Berkshires. You’ll find chefs tapping into sustainably raised, organic, and local produce to concoct incredibly delicious meals spanning geographies. 

Our favorite restaurant in downtown Great Barrington is Prairie Whale, which we think is one of the best places to eat in the Berkshires. We love grabbing a cozy table in the dimly lit restaurant and exploring their list of natural wines and seasonal food options, which change daily. 

Whether you’re looking to grab some pizza, Thai, American, or other cuisines, you’ll find dozens of great options in downtown Great Barrington. 


3. Grab something to go

Another reason we love Great Barrington is the plentiful grab-and-go options.

At the beautifully renovated Guidos, you can grab groceries and prepared foods. Similarly, Berkshire Co-Op on Bridge Street makes great sandwiches and offers a decent selection of groceries. 

A few minutes outside of downtown you’ll find Marketplace, which is our go-to for healthy on-the-go meals.

View this post on Instagram

A post shared by Rubiner’s Cheesemongers (@rubinerscheesemongers)

Downtown, we recommend checking out Rubiner’s Cheesemongers where you’ll be overwhelmed by their enormous selection of delicious cheeses. And you can’t have cheese without wine, so be sure to stop by Depart, where they’ve curated an impressive collection of natural wines that will pair perfectly with your tasty treats. 

4. Grab a cocktail at Mooncloud

After you’ve burned some calories hiking or skiing (or not!), you must stop by MoonCloud in Great Barrington for a delicious cocktail. While only a few years old, Mooncloud has made its imprint and is a must-try when visiting downtown Great Barrington and the Berkshires. 

View this post on Instagram

A post shared by Oak Hill House (@ohhberkshires)

In cooler months, cozy up in their lounge-type atmosphere. In the summer, imbibe on the front patio overlooking Railroad Street with enchanting views of the mountains. 

The cocktails are inventive, top-notch, and can be paired with their locally sourced cured meats and delicious desserts. 

5. Enjoy dessert at SoCo Creamery

We’ve been known to stop into SoCo Creamery, right on Railroad Street in Great Barrington, to grab a scoop of ice cream directly after a hike

Since 2004, SoCo has been delivering premium ice cream and sorbet to crowds of people with all your classic flavors and creative flavors (how about blueberry honey lavender? Espresso Cookie? Mocha Almond?). They’ve recently started making dairy-free ice cream, too. 

You’ll know you’re in the right place from the smell of fresh waffle cones and the smiles on people’s faces as they devour their ice cream on the sidewalk. 

6. See a performance at Mahaiwe Performing Arts Center

If you’re looking for theater in the Berkshires, you cannot miss the Mahaiwe Performing Arts Center in Great Barrington. This Berkshires concert venue and theater holds year-round events across a variety of genres. 

During your visit to the Berkshires, be sure to check the schedule of events at Mahaiwe. You might catch anything from a comedy show to an opera.

7. Enjoy the outdoors

monument mountain - great barrington, ma - best hikes in the berkshires

People flock to the Berkshires year-round due to the beautiful scenery, amazing views, and ample outdoor activities. One of the best parts about Great Barrington is the proximity to some of the best hikes in the Berkshires. You can do a hike first thing in the morning, eat lunch in town, and shop the afternoon way. It’s a great way to spend a day and something we do quite regularly. 

Perhaps the most popular hike is Monument Mountain, with a 1,642-foot summit and incredible panoramic views. 

There are three different trails at Monument Mountain. Our recommendation is the 2.4-mile Hickey and Peeskawso peak trail which takes about an hour and twenty minutes to complete. 

For something a bit more low-key and directly in town, check out the Housatonic River Walk which will take you along the Housatonic River as the name suggests. This short trail lets you see downtown Great Barrington from another angle while enjoying the sounds of the river. 

Our honorable mention is Beartown State Forest which spreads across Monterey and Great Barrington. This 12,000-acre forest is a beautiful forest in all seasons – whether hiking, boating, swimming, fishing, cross-country skiing, or snowmobiling. 

Our favorite activity in Beartown State forest is the Benedict Pond Loop Trail, an easy 1.7-mile loop around the pond that takes about 30-40 minutes to complete. Given its proximity to Oak Hill House, we love grabbing our morning coffee – especially in the fall – to walk the trail and marvel at the fall foliage as the pond’s water glistens in the morning light. 

8. Visit Ski Butternut

ski butternut - great barrington

During a winter trip to the Berkshires, Ski Butternut is not to be missed, especially given its proximity to Great Barrington and Oak Hill House. 

Ski Butternut is located about 5 minutes outside of downtown Great Barrington and is a terrific option for skiing, snowboarding and tubing for people of all ages. Ski Butternut is by far one of our favorite things to do in the winter in the Berkshires.

With 100 skiable acres, 10 lifts, and all trails equipped with snow-making capabilities, Ski Butternut brands itself as the place “where families go to play in the snow!”

Ski Butternut also has affordable midweek rates, so if you’re looking for a getaway in the winter, stopping by Ski Butternut during the week is a fantastic idea. 

10. Visit Taft Farms

The Berkshires are filled with farm stands, roadside stands, pick-your-own locations, and farmer’s markets.

The Great Barrington Farmers Market runs from May to November on Saturdays from 9 am to 1 pm and it’s a great place to stop downtown if you’re looking for some delicious produce and shop local vendors. 

But one of our favorite spots is a short drive north of town. Taft Farms is a family farm that has been operational for 55+ years and is open 7 days a week. Whether you’re picking out a plant, some farm-fresh heirloom tomatoes, or a delicious sandwich, Taft Farms has you covered. 

Our favorite part about visiting Taft Farms – and an absolute must every time we visit – is grabbing one of their tea breads or pies. Apple, pumpkin, pecan, rhubarb, peach, the list goes on and they’re all delicious. No trip to the Berkshires is complete without grabbing a mouthwatering baked good from Taft Farms.

11. Cool off at Lake Mansfield

lake mansfield - great barrington - best lakes in the berkshires

As we’ve mentioned, people flock to the Berkshires during the summer for ample outdoor activities, including cooling off in a lake. Lake Mansfield is one of the best lakes in the Berkshires and is conveniently located in Great Barrington. 

This 29-acre pond is a treasured community space, where you’ll find families cooling off during summer months or walking the conservation land around the pond. The community also holds events at Lake Mansfield, like yoga or 5k walks that provide amazing views.

12. Visit a dispensary

farnsworth dispensary - great barrington ma - best dispensaries in the berskhires

In 2016, voters in Massachusetts voted to legalize recreational marijuana. Fast forward to now, and there’s a thriving recreational marijuana industry bolstering the economy of the state. 

In the Berkshires, you’ll find multiple dispensary locations that will welcome you in and help educate you about marijuana, whether you’re a novice or have been using marijuana for years. These stores are beautifully designed and offer an array of cannabis products that are carefully curated. 

Some of our favorite dispensaries in Great Barrington are Theory Wellness, Rebelle, and Farnsworth.

13. Work remotely from a coffee shop

With hybrid and remote work models becoming the norm, we highly recommend working remotely from the Berkshires and taking advantage of all the activities the area has to offer.  

The Berkshires are home to many fantastic coffee shops conducive to working remotely, and some of our favorites are in Great Barrington.

Be sure to check out Marjoram and Roux, Fuel, and Two Flower, all of which serve up great coffee and baked goods and serve as a perfect spot to work remotely right in the center of Great Barrington.

Final thoughts on what to do in Great Barrington

If it wasn’t obvious, we love Great Barrington. We think it has some of the best hikes in the Berkshires, some of the best restaurants in the Berkshires, and some of the best arts and entertainment in the region. No matter your age or who you’re traveling with, you’ll find lots of adventure awaiting you in Great Barrington. It’s the perfect destination to spend time during your next trip to the Berkshires. 

If you’re wondering where to stay in Great Barrington, there are a few hotels and motels as well as vacation rentals close to town.

If you’re willing to be a short drive away, we recommend checking out our cozy cottage, Oak Hill House, which was recently rated one of the best Airbnbs in the Berkshires. Oak Hill House is conveniently located 11 minutes to downtown Great Barrington and is just 7 minutes to Ski Butternut, serving as the perfect home base for your next trip to the Berkshires.