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How to Plan the Perfect Weekend in the Berkshires

May 21, 2018 by Ali Bloomston
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Sure, your epic weekend in the Berkshires is going to be centered around theater and the arts, but amazing performances at Jacob’s Pillow, Barrington Stage Company, and Tanglewood only take so many hours each day. Luckily, there is so much more to do in Western Massachusetts, and we’ve assembled a guide of the best lodging, restaurants, activities to partake in when you’re not enjoying a show.

Where to Stay

Hotel on North
This adorable boutique hotel really embraces the quirky. On their website, they even admit that “some walls are not precisely straight. Ceiling heights vary. No two guest rooms are exactly alike. Every piece of décor was handpicked for its individuality.” But that is what lends Hotel on North its charm and makes it one of the most in-demand hotels in the Berkshires. It’s also the preferred hotel of Barrington Stage Company, so this is the perfect place to rest up before catching award-winning plays and musicals.

Red Lion Inn
This is the charming, colonial inn that you picture when you think of a New England getaway. It’s basically the real-life Dragonfly Inn. (“Gilmore Girls” anyone?) Voted one of the best hotels in New England by Conde Nast Traveler’s Reader’s Choice Award, Red Lion Inn has been hosting guests since 1773. The hotel has 125 guest rooms, ranging from B&B suites to individual guest houses, each uniquely decorated with antiques, and the inn also features  casual dining, a gift shop with Berkshires-made items, a casual restaurant with live music, and a pool and hot tub! The Berkshire Theatre Festival isn’t far.

(Photographed by Aimee Seavey)

Berkshires Courtyard
Surrounded by the beautiful hills of the Berkshires and only a short walk into downtown Lenox, this hotel is the Berkshires’ newest, completed in summer 2017. The views from the rooms and courtyard are breathtaking, and Marriott hospitality is always top-notch. Make sure to check out Shakespeare & Company when you’re in town.

Photographed by Ben Garver

Where to eat

Award-winning theatre should be accompanied by award-winning food. Chef Bjorn Somlo has been nominated Rising Star Chef and Best Chef Northeast by the James Beard Foundation more than once, in addition to The People’s Best New Chef for Food & Wine magazine. While the restaurant started out with a focus on pasta as the name suggests, the menu has evolved to include a variety of creative small plates and entrees. Make sure to grab a reservation as this spot is in demand!

Photographed by Ulf Nilsson

Alta Restaurant & Wine Bar
You’re in town supporting local theatre, so go one step further and eat local too! The mediterranean-inspired menu at Alta is locally-sourced from surrounding farms, including: Equinox Farm, Cricket Creek Farm, Farm Girl Farm, Berkshire Mountain Bakery, Berkshire Blue Cheese Company, Jennings Brook Farm, Mill River Farm, and Other Brother Darryl’s.

Upgrade your usual takeout routine with this Malaysian, Chinese, Thai, Indian fusion restaurant in Pittsfield. This super casual spot comes highly recommended, and is perfect for a group as you’ll want to try every dim sum and noodle option on the menu before going to a show at Barrington Stage. It’s also great for any dietary restrictions your crew might have, as all dishes can be made to be gluten-free or vegan.

Photographed by Paul Meijer

District Kitchen & Bar
Did someone call for comfort food? We dare you to try and read through this menu without your mouth watering. This Pittsfield staple whips up decadent dishes for brunch, lunch, and dinner, but we recommend this spot for brunch when you get a free mimosa or Bloody Mary with the purchase of an entree!

(Photographed by District Kitchen)

Cork N’ Hearth
Come for the fine dining and stay for the view. Located in Lee en route to Tanglewood, Cork N’ Hearth is situated on Laurel Lake, and the sunset over the water is truly postcard worthy. Go ahead and treat yourself to the french onion soup, filet mignon, and carrot cake. After all, you’re on vacation.

Photographed by Cork N’ Hearth

Where to shop

Great Barrington Antiques Center
Hitting the antique circuit is a must while weekending in the Berkshires, and if you only have time to venture to one store, this is the one to go to. This massive complex features treasures from more than 50 dealers. Whether you are looking for an antique nightstand, oriental rug, or just a cool Instagram photo of you antiquing, this is your place.

Asia Barong
The Berkshires has the largest gallery of Asian art, furniture, and sculpture in the United States, and it can be found at Asia Barong. The store advertises itself as an exotic vacation from your current vacation, and Architectural Digest, Yankee Magazine and AM New York all agree — this 25,000 piece Asian art emporium is a highlight of any trip to the Berkshires.

Photographed by Sarah Hedrych

Lee Premium Outlets
Calling all bargain hunters! This 60-store outlet mall is just a 10-minute drive from Stockbridge and Lenox, and 20 minutes from Pittsfield. Save big bucks on brands like Brooks Brothers, Calvin Klein, J. Crew, Coach, and so much more.

(Courtesy of Lee Premium Outlets)

Where to drink

Brava is the perfect location to grab post show drinks in Lenox. The vibe here is romantic and cozy, and the drink menu features pages of beers (including some local craft brews) and wines by the glass. If your stomach is grumbling from your early pre-show dinner, there are also plenty of small plates on the menu.

Photographed by Brava

Balderdash Cellars
Educational drinking? Sign us up! Owners Christian and Donna Hanson have made Pittsfield a spot on the wine-making map, producing “wicked” wines (this is Massachusetts, after all) sourced from world-class California vineyards. The tasting room is open from 1-5PM on Saturdays with live music. A tasting costs only $9 and includes seven wines!

(Photographed by Balderdash Cellars)

Patrick’s Pub
This casual Irish pub is perfect for grabbing a beer (they’ve got 16 on tap with more seasonal rotations) and some classic bar foods (voted some of the best wings in Massachusetts). Only a hop, skip, and a jump from both Berkshire Theatre Group and Barrington Stage Company, it’s perfect for a pre- or post-show drink.

What to do

Hancock Shaker Village
History nerds, rejoice! Step back in time with a visit to the Hancock Shaker Village. Established as the “City of Peace” by 100 Shakers in the 1780, the village is now a 20-building history museum with a working farm and collections of Shaker artifacts. Take a self-guided walking tour of the buildings like the meeting house, schoolhouse, and washhouse. Try the farm-to-table restaurant with food sourced from behind the restaurant (literally) and shop in the Shaker Mercantile for local goods and crafts. There’s also a barn with cows, goats, chicken, and sheep, and on the weekends during the summer they offer goat yoga!

Norman Rockwell Museum
The Norman Rockwell Museum in Pittsfield is not only home to the largest collection of Rockwell art, it is a museum established to study and preserve the art of illustration. Rockwell was famous for portraying the zeitgeist of mid-century America, and this museum showcases illustration’s ability to reflect the world in which we live. Also, Rockwell depicted the Berkshires in much of his work, so see if you recognize any of your new favorite Main Streets!

Photographed by Norman Rockwell Museum

Take a Hike
There are some who say you haven’t seen the Berkshires until you’ve hiked Monument Mountain. If you only have time for one hike, the 1.5 mile journey to the top of Monument Mountain, Squaw Peak, is a must. You’ll pass by the remains of Native American trails, walls of former pastures, and old horse and carriage roads, and the view at the top is utterly breathtaking. If you have time for another trail, we also recommend Olivia’s overlook in Stockbridge, where you have options to take a 1.5 mile loop or two different 4 mile loops. Any path you take will include the perfect vantage point of Monument Mountain.

(Photographed by Rich Thrasher)

You can find the intersection of music, sculpture, dance, film, painting, photography, and theater at MASS MoCA, a converted textile mill that is now home to some of the world’s most cutting-edge art. MASS MoCA utilizes it’s entire campus to create a unique cultural experience. Begin indoors with the enthralling 30,000 square foot Sol Lewitt: A Wall Drawing Retrospective, and then venture outside to find the Anselm Kiefer or Franz West sculpture installations. In the evenings, the parking lot is converted to a concert venue that will host acts this summer like The Decemberists and Debbie Harry of Blondie.

Photographed by MASSMoCA

Of course, we know this barely skims the surface of things to do in the Berkshires. Feel like we missed a great highlight? Email us at!