Best of the Berkshires, Massachusetts


Popularized by the summer rehearsal retreats of Bob Dylan and Yo Yo Ma, Berkshires is a perfect place to go if you are interested in a cultural mountain getaway.

Greenery and waterfalls, local cheesemongers and farms –Berkshires is an answer for those who love the arts and like to be outdoors with beautiful landscapes around. Get the most out of your Berkshires vacation and plan a getaway between June-Sep when the full region comes to life with too many summer festivals to choose from.

Where to Stay

Porches Inn

Inspired by the contemporary museum MASS MoCA, Porches Inn is a renovated small hotel that comprises of a series of row houses overlooking the canal that runs behind the museum. Located in North Adams which was originally a mill town with stunning architecture, and now transformed to a town filled with contemporary galleries and artist workshops.


Comprising an entire block of late 19th century row houses, Porches is an up-to-the-minute inn that still honors the spirit of the mill workers who lived and labored here for decades. The use of bold color and simple design elements lend an air of chic hominess that appeals to weekend escapists. The inn is named after its most distinguishing feature, the long verandas that link the six separate structures and afford ample opportunities for lounging, reading, rocking and relaxing.


47 rooms of retro-edgy ambiance make a spirited lodging statement in New England and beyond. The creature comforts are well taken care with a pool, hot tub, and one of the highlights is their breakfast in bed, the goodies come to you in a vintage trunk. It’s definitely Insta-worthy!

Porches Inn, an “industrial granny chic” boutique hotel. Opened in 2001, it features a mix of eclectic designs with 21st century technological flourishes. Catering to those looking for a mini-vacation with a cosmopolitan touch close to home, Porches provides the perfect getaway for those searching for a respite from the stifling galleries and cramped apartments of a larger northeastern city, without sacrificing taste or personal standards. – Dwell


The outdoor spaces lit with torches at night and a gathering verandah with handmade seating and campfire to keep your spirits high — Porches Inn was a lovely and graceful accommodation in the Berkshires.

Briarcliff Motel

Owned by a British couple Briarcliff Motel is a classic 60s motel that completed its transformation into a friendly 16-room hotel for today’s travelers. A stylish but basic motel, Briarcliff is an affordable (max $150) and thoughtful place to stay with personable people helping you and serving you farm fresh breakfast in the mornings. Located right in front of the Monument Mountain, in the heart of the Berkshires, and just five minutes’ drive from Great Barrington, which was recently voted as the Best Small Town in America!
Briarcliff motel
Simple room decor with comfy beds, there is a sparking red mini-fridge for you stock your beer. You would hardly notice that there isn’t a Phone in the room, as there is no Room service. The Lobby is just a few doors down, so if you need anything, just walk a few steps.


The central common area is designed like a space you would see in a high-end boutique hotel, daily breakfast is served here with an option to take your breakfast indoors or outdoors, with a side of ManU game playing in the background.

When its night time though, the main attraction is their fire place in the front garden, with seating all around. Open a bottle of bubbly and enjoy the surroundings!

Where to Eat

Prairie Whale

Prairie Whale
Prairie Whale

Brooklyn restaurant pioneer Mark Firth brings the same rustic delicious food he served at his previous restaurants Diner and Marlow & Sons, to the Berkshires. No doubt they use only the freshest produce and buy whole animals, go through all the different cuts of meat, and customize their menu daily based on the meats they secured.

Prairie Whale

If you weren’t already jealous of Berkshires residents, you will be after a meal at Prairie Whale, Great Barrington’s house-turned-rustic-kitchen formerly known as Bell and Anchor. The cozy laid-back atmosphere, ultra-fresh food, straightforward but thoughtful flavors, and pitch-perfect execution are a model for any restaurant, and I could have eaten up and down the menu.

Public Bar + Eatery

A good option when you are staying at The Porches. Love, love their flatbreads.


Nudel is a creative American pasta bar which takes its inspiration from the bounty provided by the local farms and producers of Berkshire County. Also, take a stroll down the streets and enjoy the charm of the town.


A quick pit stop at Alta to taste new wines and local cheese.

The Meat Market

Jeremy the owner of Fire Roasted Catering was popular for his commitment to using local food, and cooking on site over an open fire. It’s no doubt that when he started this butcher shop, you can see the labor of love here in this quirky retro meat-stop.

Where to Shop

Hillsdale General Store
“Useful and beautiful things for country life” is their mantra, knowing full well that some of these “country things” end up happily living in the city.

Monterey General Store
A great all-you-can-find general store in a post and beam structure that dates back to 1700s. Monterey General Store, is an awesome store to buy pantry staples, homewares, and also to fill you up with baked goods and pastries.

Cricket Creek Farm

Cricket Creek Farm
A grass-based dairy farm, also one of the oldest dairy farms in the region.  Their primary activity is raising dairy cows for their good milk and artisanal cheese in their farmstead creamery. With a bakery on site, and vast grounds around, you can lay around and have an impromptu picnic.

One Merchantile
Owned by a couple whose shared interest is to score all things vintage and exceptional goods. You will find unique one of a kind items, and small production fair-trade goods.



Rubiners is where you go, if you like to be in Cheese heaven!

No. Six Depot
An unique cafe that is part coffee shop, gallery, and event space. They source local teas and coffees and roast it right there, this place makes you feel at home.

What to Do

Mass MoCa


MASS MoCA is housed in a 13-acre campus of renovated 19th-century factory buildings in North Adams, Massachusetts. The complex occupies nearly one-third of the downtown business district. It’s quite possibly the best museum building I have seen — with a mix of the old and new, industrial and modern, the contemporary artwork housed in the museum feels like an extension to the building.
Also, check out the Lickety Split Cafe in the museum campus and be entertained by the local musicians playing during the weekends.

Shakespeare and Company

No intro needed here, except, it’s quite an experience to watch A Midsummer’s Night Dream in the woods. Highly reco’d!

Bash Bish Falls

In the extreme southwest corner of the state is a cluster of state parks noted for their spectacular scenery and breathtaking views. Bash Bish Falls is one of the Massachusetts’ most dramatic and highest single-drop waterfall. This is the place to unwind and take your mind off of the impending hectic week that is about to begin Monday!

Curator. Dreamer. Designer. Founder of FreshGrub. Based in NYC. Seeking Inspiration Everywhere.

Be first to comment

Leave a Reply