Get Out There | The Berkshire High Guide

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Get Out There

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The Berkshires

At a Glance

Berkshire County is celebrated for its rich culture and beautiful scenery. Spanning the entire vertical length of the westernmost portion of Massachusetts, it is a sharp contrast from the city of Boston. Locals and tourists alike enjoy the abundance of small and unique businesses, the year-round outdoor activities, and the easy-going community. 


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Best Places to Stay

Egremont Village Inn

The Egremont Village Inn has a blend of both cultural and historical feats. The building dates back to 1786, qualifying it as one of the oldest buildings around the area. While there have been additions added to the property, the building is still very similar in appearance to the dated,…

Red Lion Inn

The Red Lion Inn has been welcoming guests since roughly 1773. The hotel is quite large and sits beautifully on Main Street in Stockbridge. Six United States presidents, travelers, musicians, business personnel, authors, and locals alike have come to the inn for its serenity, antiques, art, and…

Gedney Farm

Gedney Farm is a bed and breakfast like none other in the area. The architecture resembles the elegant Normandy barns of nineteenth century France. The barns onsite were actually built with the intention to host and exhibit the most beautiful stallions and cattle around, and that it did—up until…

Race Brook Lodge

Race Brook Lodge is a wonderful place to relax and rewind. It is located right next to a picturesque hiking destination that shares a similar name—Race Brook Falls. The architecture is charming and rustic. Directly outdoors, guests are able to access the surrounding trails with ease, including…

Canyon Ranch

Canyon Ranch is a luxurious getaway destination in Lenox. People from all over—and Berkshire locals—come here to escape, relax, and enjoy the expansive amount of lavish health-oriented services offered. There is a spa, plenty of wellness activities (try a yoga class), a lake to canoe in,…


Designed for the 21st-century traveler, the Tourists hotel maintains a rustic look that intertwines with a mid-century interior that is surprisingly contemporary. Surrounded by the greenery of the Berkshires, it has a forest waiting to be explored and trails perfect for a morning walk or run. It…

The Wainwright Inn

The Wainwright Inn is saturated in rich and authentic Berkshire County culture. It is known by those who live in the area as a local landmark—located conveniently on Rt 7 in Great Barrington. 

The story of the inn begins in 1766, when Captain Peter Ingersoll started constructing the main…

Hotel on North

Hotel on North is a medium-sized place to stay that is favored among both by tourists and those from the area. It has an unparalleled design where every room is unlike the others and is decorated with handpicked items. This gives its visitors a new experience with every visit. There is space for…

Staveleigh House Bed and Breakfast

The Staveleigh House is a beautiful bed and breakfast on Sheffield's Main Street—the southern gateway into Berkshire County. Interestingly, it was built in 1821 for the pastor of the Old Parish Church, sharing a past with the historical town. Despite being located on a main road, the home has a…

Old Inn on the Green

The historic and culture-rich Old Inn on the Green is located in the scenic village of New Marlborough. It’s encompassed by lush meadows and expansive fields. At one point, it was actually a stagecoach relay, but now offers dining, lodging, event planning, and catering services. When it comes to…

Bascom Lodge

There’s plenty of things to do and see at Mt. Greylock State park, but the coziest might be sitting down for a meal at Bascom Lodge. This flagship property of the department of conservation and recreation was built by the Civilian Conservation Corps (CCC) in the 1930’s. The rustic stone and wood…


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What to See Now


Field Farm

Hairpin Turn Route 2


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Best Places to Eat/Drink


Bizen is frequently called “the best sushi in western Massachusetts” by those who venture into the restaurant—and for a handful of great reasons! The Japanese cuisine is fresh, flavorful, vibrant, and authentic with an immaculate presentation. It’s tucked into a popular Great Barrington shopping…

Cantina 229

There’s a curious modern building nestled into the picturesque countryside along Route 183 heading toward New Marlborough, Massachusetts—inside you’ll find an oasis of casual fine dining: Cantina 229. Restaurant-baby of Josh & Emily Irwin, showcases a playful nouveau American cuisine and a…

Dream Away Lodge

On the edge of the largest state forest in Massachusetts lives a larger than life hang out called the Dream Away Lodge. This old farmhouse has a little bit of everything: theatre, restaurant, and music venue, set on a large property with manicured gardens, walking trails, a meditation field, and…

The Prairie Whale

The Prairie Whale, located on Great Barrington’s Main Street, is an interesting fusion of Brooklyn and Berkshire dining. It has a rustic aesthetic and savory menu that attracts both locals and those just stopping by in the area. The low-lit, cabinesque decor is really relaxing and homely, but…

Berkshire Mountain Distillers

Berkshire Mountain Distillers is Berkshire County’s first legal distillery since the times of prohibition. Operations began in an old barn and lasted for years, but they are now located in Sheffield and have tastings, tours, and retail options. The distillery has a grain-to-glass philosophy and…

Bistro Box

The only lines longer than the ones at the dispensaries in Great Barrington, is the line to order food from the Bistro Box! Open from April through November, this casual roadside eatery serves fresh, playful food, at a price that won’t break the bank. 

Chef-owers Nick and Birdie are both…

The Barn

The Barn is a world-class, live music venue with great artists/bands, great food (try the shrimp tacos with a side of guacamole), big drinks, and legitimate old barn ambiance. Rock, folk, soul, reggae, country, jam, all of it from local talent and touring artists who just want to be in the…

SoCo Creamery

One of the best places to cool down in Great Barrington is on Railroad Street—SoCo Creamery! Founded in 2004, this ice cream shop has a wide and ever-evolving variety of flavors to fit any preferred flavor palate. SoCo’s ice cream is handcrafted right in their kitchen, with dairy from Kingdom…

Baba Louie's

Healthy, delicious, comforting... that's exactly what comes to mind when we think of Baba Louie’s in the ever-lively, downtown area of Great Barrington! There’s a pretty amazing array of options baked beautifully together to form a symphony of flavors for everyone in the family! Of note, vegan…

Marketplace Café

The Marketplace Cafe is a great place to grab a bite to eat in Berkshire County. It has several locations and variations in the area (other cafes, Marketplace Kitchen Table, and Specialty Foods at Guido’s in Great Barrington). The menu is quite extensive for a fast-casual eatery and varies at…

The Old Mill

Walking up to The Old Mill, over the river, for dinner, expect to be hosted by Terry Moore who has been running the mill for over forty years now. The dishes served here are both traditional and exotic with a dash of creativity to liven the meal. The diner is kept neat and the wide wooden planks…


Public is a popular spot to grab a drink and a bite to eat in North Adams. It’s right next to MASS MoCA and serves delicious American cuisine (ther grilled Bistro Steak meal is a must try). They offer small plates, large plates, lunch, dinner, desserts, sides, and delicious drinks. All of the…

Hikes & Adventures

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Where to Explore

Hopkins Memorial Forest

Jiminy Peak

Monument Mountain


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Best Places to Shop

Railroad Street

Off of the Main Street shopping strip in Great Barrington, Railroad Street is packed with a variety of entertaining places to visit ranging from eateries to clothing retailers. These local businesses are unique and cater to an array of experiences. Bizen is home to a delicious sushi bar and has…

Barrington Outfitters

Barrington Outfitters is wonderfully eclectic and exciting. This is because the store features a variety of clothing, footwear, accessories, and furniture—both for indoors and outdoors. It has been in operation and catering to the community for over 25 years, as it was opened back in 1994. …

The Pass

The Pass is a cutting-edge adult-use recreational cannabis dispensary in Sheffield. The facility is fully-integrated and continually pushing to produce the most remarkable, reliable cannabis products around with a strong Farm to Label philosophy. Everything is grown, processed, and sold at the…

The Bookstore

Inspiration abounds in the Berkshires and many authors, the likes of Edith Warton and Nathaniel Hawthorne, have escaped to these emerald hills. It’s no wonder that one of the last great independent bookstores is located in Lenox, Massachusetts.

The Bookstore and it’s fantastically…

Boho Exchange

The sweetest little store, in the sweetest little house–we adore Boho Exchange! If you are a super thrifty shopper, and seeking outfits of any sort, be it dressy, casual, or for a trip into nature, Boho Exchange is one of the best places to stop. This place is eclectic and electric.


Charles H. Baldwin & Sons

Charles H. Baldwin & Sons dates back to 1888, even though the family had been making extracts for generations prior to opening the business. They specialize in extracts (especially pure vanilla extract), table syrup, spices, various baking supplies, bloody mary mix, worcestershire sauce,…

The Book Loft

A Book Lover’s Dream.

The Book Loft is an impressive book store located in the Barrington Plaza selling a wide range of books for anyone who loves reading, from children right up to senior citizens. The store opened in 1974 and has since become a favorite for both local and visiting book…

Explore Towns




Great Barrington






New Marlborough

North Adams





West Stockbridge



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