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A photo of the afternoon sun over a farm on Baldwin Hill in Egremont, Mass. photo by Isabel Costa.
The afternoon sun over a farm on Baldwin Hill in Egremont, Mass. photo by Isabel Costa.
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Travel Bug Playcation:
Great Barrington

A dozen destinations to add to your day trip To-Dos for that local-izing effect.

Above: The afternoon sun over a farm on Baldwin Hill in Egremont, Mass. photo by Isabel Costa.

Crowned as the “Best small town in America” by Smithsonian Magazine in 2012, Great Barrington, Mass. is still the best example of a quintessential and picturesque New England small town. It is the home to many urban and suburban transplants searching for a better lifestyle. Main Street and Railroad Street are lined with unique high-end boutiques, family-run businesses, galleries, toy shops, and restaurants. Picking up a guide at the Visitors Center, you will find the most popular parks, restaurants, and museums to fill your days. The top visitor destinations are a great way to explore Great Barrington, but the places we share will have you spending your day like a true local.

Editor’s note: The Greylock Glass received no compensation for featuring these businesses in this article.

Grab a coffee at Patisserie Lenox

Photo of retail cafe and bakery, Patisserie Lenox; by Isabel Costa.
Patisserie Lenox; photo by Isabel Costa.

You don’t have to visit France to capture the authentic French bistro experience. Patisserie Lenox is owned by French chef Jean Yves. Yves has worked in the restaurant business for 40 years and graduated at the top of his class from the famous pastry school, Ecole Jean Ferrandi located in Paris, France. Walking through the door, customers are promptly greeted with the smell of croissants, chocolate, and éclairs fresh from the oven. Freshly brewed espresso is constantly looming through the air. Customers can sit inside or outside under the French-inspired awning, watching the flow of life as if being transported to a traditional French café.


Enjoy your coffee while experiencing Baldwin Hill

A photo of a Baldwin Hill corn field just a couple weeks this side of ripe; photo by Isabel Costa.
A Baldwin Hill corn field just a couple weeks this side of ripe; photo by Isabel Costa.

Baldwin Hill is located 5 minutes from Great Barrington in North Egremont, Mass. It is encased in a 360-degree moving image of one of the most breathtaking snapshots of nature. Surrounded by farmland, cornfields, and rolling hills a walk through this Van Gogh landscape will evoke a sense of inner peace and reawaking.


GB Eats, A restaurant for delicious meals throughout the day

Photo of the restaurant GB Eats; photo by Isabel Costa
GB Eats; photo by Isabel Costa

GB Eats located right on Main St., has a line up of dishes from eggs to pancakes to mouth-watering juicy burgers. They offer a varied menu using only the freshest ingredients. The egg dishes are stellar, and the adult drink menu is impressive, as well as their extensive coffee menu. All dishes are reasonably priced and cooked to perfection . You don’t want to skip on this spot to start your day.


Yellow House Books

Photo of front entrance of Yellow House Books; photo by Isabel Costa.
Yellow House Books; photo by Isabel Costa.

Yellow House Books houses a broad selection of new and older books, magazines, and sheet music. The older books make great conversation for families as their large selection allows customers to read through many generations of fantastic literature.
Ripley, the gray tabby, will also help you find the best book for you or your family.


Tea for a good cause at Extra Special Teas

Photo of front entrance of cafe, Extra Special Teas; photo by Isabel Costa.
Extra Special Teas; photo by Isabel Costa.

Extra Special Teas is located at 2 Elm St. in Great Barrington. Started by Scott and Cheri Sanes, Extra Especial Teas brings working opportunities for adults with developmental and intellectual disabilities. Walking up to the shop, customers are greeted with an environment of acceptance and love. Bright colored flowers and pinwheels line the front steps, as well as a bright orange door to promote a happy feeling while entering this special tea house.


A Roadside eatery brings delectable burgers and tasty sauces

Photo of the roadside eatery, The Bistro Box; photo by Isabel Costa.
Roadside eatery, The Bistro Box; photo by Isabel Costa.

The Bistro Box is a popular roadside eatery located on Route seven and houses yummy burgers, salads, parmesan fries, and a heavenly house sauce. Perfect for couples or families, the outside eating area has open fields for picnics and a cornhole table for family games.


Theory Wellness for Cannabis Needs

Theory Wellness; photo by Isabel Costa.

For folks, 21+ Theory Wellness offers a wide range of quality cannabis products. Customers can pre-order items online and pick up curbside or buy products in-store. Theory offers a range of cannabis products such as cannabis-infused seltzers, vaporizers, edibles, and a range of flowers to choose from. Customers will be greeted by “budtenders” who will guide you through purchasing the best cannabis-infused products for your lifestyle.


Matrushka Toys and Gifts They will Remember

Matrushka Toys opened in 1991 in the lobby of the Great Barrington Waldorf school as a small not-for-profit shop, displaying many beautiful toys, a majority of them handmade to perfection. Today Matrushka Toys is owned by Brook Redpath, who consistently strives to curate open-ended toys to help children at any stage of development.


Catwalk Boutique

Sales from the Catwalk Boutique benefit the Berkshire Humane Society; photos by Isabel Costa.

The Berkshire Humane Society has been helping animals since 1992. At Catwalk Boutique, customers can shop while supporting the lives of animals as 100 percent of the proceeds go back to The Berkshire Humane Society. With a newly expanded space, Catwalk always has highly fashionable pieces on display. With thrifting as trendy as it has been, a trip to Catwalk to browse through their selection of clothing, handbags, shoes, and other apparel is a must-see.


Monument Mountain

Photo, taken from Devil's Pulpit, left, on Monument Mountain in the Berkshires, Massachusetts.
Devil’s Pulpit, left, on Monument Mountain in the Berkshires, Massachusetts; photo by Mwanner, CC BY-SA 4.0

Welcoming some 20,000 visitors per year, Monument Mountain is an exquisite terrain fit for both advanced and beginner hikers. The view at the top is both rewarding and breathtaking and well worth the climb. One side of the mountain is steep for more advanced hikers, and the other side is easier for beginners. The top of the mountain is a visual oasis, which is guaranteed to sooth your soul.


Dinner at Agaves Mexican Grill or Aegean Breeze

Agaves serves a modern twist on favorite Mexican dishes. Located on Route seven. Agaves has an open patio seating area as well as comfortable indoor dining. Nestor and Sandy take traditional dishes from Nestor’s home in Oaxaca, Mexico, and play with flavor and experimentation. Anyone of their taco dishes will merge with your tastebuds in harmony, and their Oaxaca Omelet will be a perfect brunch dish.

Transport yourself to the angelic Grecian islands and enjoy exceptional traditional Greek dishes with indoor and outdoor dining. Aegean Breeze offers many tasty dishes as well as a substantial drink menu to serve any drink order. Chef Cami specializes in savory whole fish and tilapia dishes. The inside of the restaurant offers a cozy rustic feeling with a spacious dining area. The outdoor patio area is reminiscent of the Greek isles on a warm evening.

  • Photo of the sign for the restaurant, Agaves Mexican Grill; photo by Isabel Costa.
  • A photo of the entrance to Aegean Breeze Restaurant, Mediterranean cuisine; photo by Isabel Cost.


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