One of the things I love about travel is revisiting a place I’ve been to years ago and rediscovering everything I loved about the destination in the first place. And that’s exactly how I feel about Great Barrington, in the Berkshires in Massachusetts.
I recently spent a weekend getaway in Great Barrington in the Berkshires with my husband’s family and we had such a great time hiking, eating, shopping, and exploring. Now I want to share everything we did so you can plan the perfect weekend in Great Barrington as well. So keep reading for all of my travel tips and recommendations!
Where is Great Barrington?
Great Barrington is located in the Berkshires, a rural region in the mountains in Western Massachusetts. While the Berkshires is full of small, charming towns like Lenox, Stockbridge, and North Adams, Great Barrington is the perfect town to base yourself for exploring the entire region. And I’m not the only one who feels this way. According to Airbnb, it’s the most popular town to visit in the Berkshires.
Great Barrington is also the largest town in the Southern Berkshires and offers a very pedestrian-friendly town. Its main thoroughfares are lined with well-curated shops and popular restaurants. Great Barrington was also officially named an Appalachian Trail community in 2009, which makes it a popular stop for hikers and the perfect weekend getaway in the Berkshires for city dwellers alike.
How Do You Get to Great Barrington?
There are three ways to get from New York City to Great Barrington, by bus, train, or car. A car is the most direct option.
You can also take a Peter Pan bus from the Port Authority bus station. The pros of taking the bus are that it’s only a 3-hour ride and the bus drops you directly in Great Barrington. The con is that this bus service is currently only offered 3 times a week, Fridays through Sundays, at 9:30 am.
You can also travel via train. Amtrak has just introduced its Berkshire Flyer direct service between Manhattan and Pittsfield, Massachusetts. This option is only available during the summer but it’s a great alternative if you don’t have access to a car. Pittsfield is about a 30-minute drive to Great Barrington and car share services are readily available in the area. An alternative is to take an Amtrak train to Hudson, NY. From there, it’s a 45-minute drive to Great Barrington.
The Best Time of Year to Visit Great Barrington
One of the things I love about Great Barrington and the Berkshires, in general, is that it’s an area worth exploring year-round. If you visit in the winter, you can go skiing and enjoy a variety of winter sports. In the spring, you can enjoy hiking or a stroll through town. There are also many great museums in the area where you can take in some culture. Summertime means you can enjoy all of the typical outdoor activities. Plus, the region really comes alive with a variety of cultural events and festivals. And lastly, in the fall, visit during peak foliage to take in the magical colors of the leaves.
Great Barrington Travel Guide:
One of the bedrooms at our Airbnb property
The dining room at our Posto Property Airbnb
Where to Stay:
When we visited Great Barrington, we rented an Airbnb property in nearby Monterey through Posto Property Management. It was a great option for us because we were a larger group and needed 4 bedrooms and Monterey is a quick, 10-minute drive to Great Barrington.
I highly recommend all of the properties run in the Berkshires (and the Hudson Valley) by Posto Property Management because the management team did a great job of communicating with us and stocking the home with everything we needed. Also, they have been kind enough to extend a 5% discount on bookings to all of my readers! Just mention Let’s Be Merry on Airbnb when booking your reservation, or if you book directly through the Posto Property website, use the coupon code LETSBEMERRY for the 5% discount.
There are also some great hotels and Bed and Breakfasts in the Berkshires if that’s more your speed:
- Granville House – a 5 guestroom Inn with friendly hosts located near Great Barrington
- Red Lion Inn – For a splurge, a quintessential Berkshire hotel located in Stockbridge
- Race Book Lodge – a rustic retreat offering peaceful respite and outstanding hospitality
Places to Eat & Drink + Coffee:
- Moon Cloud – A cozy cocktail lounge serving specialty drinks and charcuterie boards
- Marjoram + Roux – a cool coffee shop serving locally sourced breakfast and lunch
- Pixie Boulangerie – a community bakery offering an array of baked goods and treats
- Prairie Whale – Elevated cuisine and artisanal cocktails served in a hip, rustic setting. The owner is also one of the founders of Marlow and Sons in Williamsburg, Brooklyn.
- Baba Louie’s – an artisan pizza shop offering thin-crust pizzas, including gluten-free pizza!
- Steam – Amazing and authentic Thai food in Great Barrington
- Bizen – A gourmet Japanese restaurant and sushi bar
- Soco Creamery – This ice cream shop is an institution in Great Barrington
- Fuel – A hip coffee shop serving breakfast, brunch and lunch plus a variety of espresso drinks.
Things to Do in and near Great Barrington:
- Monument Mountain – A pleasant and moderate hike that’s also great for kids
- The Egremont Barn – Get your fill of live music here while enjoying local food and drinks
- Housatonic River Walk – Get close to nature by taking a stroll on this flat walkway
- Norman Rockwell Museum – In nearby Stockbridge and worth a visit if you’re a fan of the artist
- The Mount – Edith Wharton’s former home and now a historic museum and cultural center
- High Lawn Farm – A working dairy farm in nearby Lee serving homemade ice cream
Where to Shop in Great Barrington:
- Home Love – A unique, colorful home décor and gift shop
- Depart Wine – A stylish wine and beer shop with knowledgable and friendly staff
- Rubiner’s Cheesemongers – If you love cheese, you HAVE to visit this shop. It’s cheese heaven!
- Familiar Trees – A carefully curated coffee table book shop with rotating art displays
- Crystal Essence – A magical shop selling crystals, gems, jewelry, new age books, and more
- T.P. Saddleblanket – Selling all things Western
- Fluff – If you’re into artisanal alpaca goods then this place is for you
- Farnsworth – the coolest-looking dispensary I’ve ever seen
- JWS Art Supplies – A Haven for artists, offering high-quality and beginner art supplies
Are You Ready to Visit Great Barrington in the Berkshires?
So what do you think? Are you ready to plan a weekend getaway to Great Barrington in the Berkshires?
I hope this travel guide is the inspiration you need for your next trip!
If you’re looking for other great destinations in New England, make sure you check out my posts about Maine:
10 Coastal Towns in Maine Worth Visiting
Mid-Coast Maine: a 5-Day Itinerary
New England Road Trips: 9 Amazing Destinations
A Foodie’s Paradise: Exploring the Best Restaurants in Providence
12 Comments
Lindsey Schmid
August 17, 2022 at 9:20 amOn your next visit be sure to reach out to us at 1Berkshire, we are the official regional destination marketing and economic development agency for the Berkshires and run the berkshires.org site which is the quintessential Berkshire planning tool. We work with journalists all the time to plan familiarization tours. Glad you enjoyed your time #intheberkshires!
Merry Lerner
August 19, 2022 at 8:39 amI definitely will! I’m sure that you have a wealth of knowledge of the region that my readers and I would benefit from!
tom
August 16, 2022 at 9:31 amGreat Tips!
Emily
August 15, 2022 at 12:57 pmYou forgot the super cool art store!!! Jws art supplies right next to baba Louie’s!
Merry Lerner
August 15, 2022 at 4:55 pmAh ok! I will add this to the post and thanks for the tip! 🙂
FRANK POTASH
August 15, 2022 at 10:10 amThe bus from NYC is only 3 hours, not 5.5. Other train possibilities are Metro North to Wassaic or Amtrak to Hudson, NY — both of which run many times a day, every day. Research, people!
Merry Lerner
August 15, 2022 at 4:58 pmThank you for these tips! The last time I checked, the bus was 5 hours from Port Authority but I will update my post now. Also, Hudson, NY is a bit further than Pittsfield (a 45 min drive) which is why I didn’t originally include it, but I will add it because I agree it’s great for readers to know about all of the available options.
Frank Potash
August 15, 2022 at 7:14 pmThanks for making these updates! The transportation situation is ever evolving — the buses were twice daily before covid, and hopefully will become more frequent as time moves on. When I was college-aged, Greyhound ran daily express buses to Pittsfield, but alas, no more for now. There is a movement to get the Housatonic train line from Danbury to Pittsfield up and running again, which would be great and serve a plethora of towns in NW CT and the Berkshires. There is a lot of interest upgrading transit options to both NYC and Boston — fingers crossed!
Nan Wile
August 14, 2022 at 12:29 pmGreat Barrington, and the other neighboring towns you mentioned in the Berkshire Hills, offer culture and recreation with amines to choose from. That’s for sure! It’s noteworthy that the GB has recently chosen to preserve the community that built the infra structure and attractions that draw visitor to the region like many other towns across the country. They whole heartedly welcome vacationers and also have in place moderate regulations on short term rental properties in their village, opting to retain housing for its families and workforce. Thank you for pointing out that you rented in nearly Monterey – illustrating rentals in neighboring towns provide amble convenient housing choices – that allows GB economy to flourish hand in hand with beautiful neighboring towns in the area. Excellent article!
Merry Lerner
August 15, 2022 at 4:59 pmI’m so glad you liked this article and I agree it’s so important to have a balance between short-term housing options for visitors and affordable housing for locals in the community.
ANUKRATI DOSI
August 12, 2022 at 5:15 amThank you for sharing such a comprehensive guide. The photos are incredibly beautiful.
Merry Lerner
August 13, 2022 at 4:31 pmI’m so glad you liked the travel guide and the photos! I hope you get to visit Great Barrington and the Berkshires soon.