A weekend in the Berkshires: Putting the “high” in highbrow


The quaint towns that make up the Berkshires feel straight out of a Norman Rockwell painting. Photo: @later_nyc

You may think of the Berkshires in Western Massachusetts as a vacation spot for highbrow intellectuals. It is. Just about every night of the week during summer, Tanglewood has offered outdoor performances by the Boston Symphony, the Boston POPS, and various jazz musicians and chamber players since the 1930s. There is also a literary heritage to the area that would make your head spin. Lately, though, you can feel the Brooklyn vibe, as borough transplants open restaurants and hotels, and more and more New York residents are visiting and investing in real estate. This makes sense: For New Yorkers it’s a quick three-hour drive, providing country air as well as a cultural paradise with centers for art, great food, and music venues. In between Tanglewood and the fussy bed and breakfasts, there is also an adorable cheese shop, a perfect dive bar, and a stylized roadside motel, too. It’s possible to pivot from skiing on the mountain one morning to spending the afternoon at a top museum. Plus, did I mention a recreational weed dispensary just opened? Here’s everything you need to know for a weekend away in the Berkshires.

An Airbnb might be your best option depending on the size of your group. Photo: @later_nyc

Where to stay


The spread of the Berkshires is over an hour stretching from Great Barrington to the south to North Adams on the border of Vermont. Both times I’ve visited recently, I’ve managed to get as far as Great Barrington before I maxed out on my driving enthusiasm. Going anywhere with a posse of children is difficult in the best of times, but in winter, being confined to a hotel room feels like torture. Therefore, Airbnb is a great option. We stayed at Alexa & Jake’s completely renovated home ($245/night) that sleeps 10 comfortably just minutes from the downtown. A kitchen table fit for a large gathering anchored us to the spacious kitchen where we spread out cooking a makeshift dinner the first night. An outdoor grill worked magic on our fish (even in the winter.) The bedrooms are nicely spread out with an enormous room complete with four twin beds, perfect for a brood of kids. The downstairs bedroom connects to a dreamy sun porch, and the master bedroom has space enough for a yoga class if you can pry yourself out of soaking in the clawfoot tub. So much wine was drunk in front of the burning fireplace, before passing out on a crazy comfortable mattress in the silence of the country.

A renovated roadside motel offers a firepit on the base of a mountain. Photo: @briarcliffmotel

The Briarcliff Motel

When you’re looking for a quick getaway that won’t break the bank, let me recommend The Briarcliff Motel, a 60s style roadside motel that was fully renovated in 2016. Each room is bright and nicely designed with Marimekko bedding and quirky touches throughout. It sits at the foot of Monument mountain, giving easy access to hikes and nature. It’s not fancy, but it checks all the cool boxes and is situated conveniently to everything. Mornings include a hearty breakfast in the comfortable lobby while evenings are best spent in front of the firepit talking with the other visitors about which neighborhood in Brooklyn you hail from. The Briarcliff Motel, at Monument Mountain, Route #7, Great Barrington. Rates around $240/ night for 2 adults. Pets allowed.

Tourists are definitely welcome at this beautiful retreat in the woods. Photo: @touristswelcome


In North Adams, at the border of Vermont, is a new “retreat” called Tourists that’s gotten a lot of press since the owners include the bassist from Wilco and the founder of Brooklyn Magazine, and the restaurant is run by a James Beard Award-winning chef. The decor, as shown on the website and Instagram, combines exposed wood, glass, and views for days. All of this could end up being fussy, but at around $300/room, the hotel seems intent on being an accommodation that helps you connect with nature and the surrounding towns and not a fortress to hide in. From here, you’d be close to Mass MOCA and the Clark Art Institute, both world-class institutions with much to offer the weekender. (In contrast, most of this itinerary focuses on the Southern part of the Berkshires.) Evenings can be spent stargazing by the fire pit or swimming in the pool during the warmer months. Although I haven’t been yet, it will be on my spring bucket list. Tourists, 915 State Rd, North Adams. Rates around $300/ night.

Stock up on gourmet cheeses and other picnic supplies here. Photo: @rubinerscheesemongers

Where to eat & drink

Rubiner’s Cheesemongers

Every weekend to the Berkshires should start with stocking up at Rubiners. Here’s a sampling of what you could find the last time I was there. Winnimere cheese (a decadent cheese only made during the winter months), french butter, Wabash Cannonball goat cheese, fondue-in-a-bag, red onion marmalade, biscotti, ring dings, local eggs from nearby farms, and boxes of toffee. If all this makes you too hungry to leave without eating, you can stop into Rubi’s in the back which sells sandwiches and espresso with tables on which to feast. Rubiners, 264 Main St., Great Barrington.

Beware if you go to this restaurant the first night, you may be back every remaining night. Photo: @later_nyc

The Prairie Whale

Some of my all-time favorite restaurants include Diner and Marlow & Sons, so of course, I was interested in dining at The Prairie Whale, a restaurant in Great Barrington opened by Mark Firth, a founder of those Brooklyn institutions. My first time in Great Barrington, I made various restaurant reservations all over the county, but after the first night at Prairie Whale, I canceled them all and just came back for dinner every succeeding night. The name stems from the 19th-century term for a pig, and the meat-heavy menu includes an incredible grass-fed cheeseburger, a brick chicken that was simple yet succulent, and a fried chicken that was served with cornbread and maple butter. The vibe inside is a comfortable pub that encourages lingering and meeting with old friends. Outside, during the summer months, there are cornhole games and customers waiting for a table in the sun holding a beer. It’s unpretentious yet cool—a perfect mix of Brooklyn and Berkshires. The Prairie Whale, 178 Main St., Great Barrington.

A simple breakfast sandwich is done well at GB Eats. Photo: @later_nyc

GB Eats

You’re on vacation, so you should probably sleep in. But whether you are up with the chickens or rolling out of bed after the cows come home, there will be eggs waiting for you at GB Eats. This bustling bistro does a brisk business of omelets, pancakes, and burgers. There is also a wide selection of lattes, cappuccinos, and coffees, but even more popular seemed to be the flowing bloody mary’s. It’s a casual and crowded place. While we were there the credit card machine malfunctioned and the waitress yelled to her table, “better have some cash!” Luckily there was an ATM machine outside, but be ready to be flexible and ready to roll with it. GB Eats, 282 Main St., Great Barrington.

This is the candy shop of your dreams (and your dentist’s nightmares.) Photo: @later_nyc

Robin’s Candy

There is no real reason why adults should be so excited by a candy store, but I can attest that Robin’s Candy is pretty magical. It’s filled to the brims with selections of classic New England (Sky bars, Clark bars, Boston Baked Beans) and nouveau choices (tiny chocolate mice, bacon pralines.) There are also novelty gifts like hangover drops or Mary Janes candy joints. Pop your head in, even if you don’t have a sweet tooth. It’s an interesting experience that will be worth a mint on your Instagram if nothing else. Robin’s Candy, 288 Main St., Great Barrington.

There is no Coors Light served at this perfect dive bar, but there is craft beer and whiskey. Photo: @nocoorslight

Moe’s Tavern

What’s the best bar in the Berkshires? Well, the people have spoken, and the winner is Moe’s Tavern. It was voted “The Best Bar in the Berkshires” by the Berkshire Eagle Readers Poll in 2018, and it turns out that all these responders were correct. This might actually be the best bar ever, anywhere. It’s a dive bar for a craft beer community (their website is nocoorslight.com) that doesn’t feel depressing during the day or obnoxious at night. You can watch the game, you can flirt with strangers, and you can even order a pizza to be delivered—as I witnessed on my last visit. Moe’s Tavern, 10 Railroad St., Lee.

Even if you haven’t skied for years (or ever!), Butternut should be on your to-do list. Photo: @later_nyc

What to do

Butternut Ski Mountain

The Berkshires is amazing because there is skiing in the winter and nature in the summer. Butternut is a perfect mountain for learning to ski. The trails are well groomed and maintained. There are classes every half hour for newbies, that you can sign up for the same day. There are kid’s ski schools to keep kids engaged and having fun. There are enough chairlifts to keep the lines down, especially on non-holiday weekends when the mountain is not that crowded, but it offers enough slopes for different levels that there is something for everyone. You can rent all the gear there, including a seasonal ski rental, if you plan to go a lot. Butternut Mountain, 380 State Rd., Great Barrington.

You’ll be amazed at how much of Norman Rockwell’s canon of work you will immediately recognize. Photo: @later_nyc

The Norman Rockwell Museum

If the tiny, charming towns of the Berkshires make you gasp with how antiquated and small-town Americana it all feels, you’re not alone. Norman Rockwell lived and worked in Stockbridge, on a property that has since been converted to the Norman Rockwell Museum. A visit to the museum means an astonishing retrospective of all of Rockwell’s work which has left an indelible impression on the makings of American myths. It’s amazing how many of his paintings everyone knows. Also, it’s possible to step into his studio, a beautiful separated house where you can just imagine creating Saturday Evening Post covers while smoking a pipe. Norman Rockwell Museum, 9 Glendale Rd., Stockbridge, MA. Open 7 days a week. $20 adults, free for kids.

On a sunny day, the Terrace Cafe at The Mount would be the perfect place for lunch (preferably with a book for company.) Photo: @later_nyc

The home of Edith Wharton

There must be something in the water in the Berkshires because there is no shortage of creative talent to come out of the area. Bookworms will be overjoyed with a literary tour through writer’s workplaces. Start with The Mount, Edith Wharton’s house, an unparalleled estate with beautiful gardens for wandering and a tour of the mansion in which she lived and worked. If it’s a nice day, you could plan to have lunch on the Terrace Cafe or attend one of many events that happen year-round on the grounds. (I can’t wait to return for one of the Ghost Tours they offer in the fall.) The author of books like The Age of Innocence and Ethan Frome wrote about high society and lived the life herself. It’s breathtaking to see the remnants from these times gone by. Don’t forget to stop in the delightful gift shop. The Mount, 2 Plunkett St., Lenox, MA. Tickets: $20 adults, $18 seniors, $13 students, free for kids.

This is the desk where Moby Dick was actually written. Photo: @later_nyc

The home of Herman Melville

Herman Melville’s house, on the other hand, is a modest affair. Compared to the Mount, Arrowhead is a dreary place that feels haunted with oppressive depression. It’s not that it’s a small house, it’s just that it’s dark and in the upstairs bedrooms where he lived with his large family, Melville used half of the floor for his office. It’s a fascinating look at one of America’s most well-known authors. He wrote Moby Dick here, and if you visit the house, a guided tour will tell you all about his life and his work. It’s even possible to follow a Melville trail around the Berkshires, for those who’d like to see where his inspirations came from. Arrowhead, 780 Holmes Rd., Pittsfield, MA. Tickets: $15.

Get to this wellness center before it opens to avoid standing in a 90-minute line for cannabis tinctures, vape pens, flower and edibles. Photo: @later_nyc

Theory Dispensary

Recreational marijuana is legal now in Massachusetts, and everyone is excited. Theory Wellness, a recreational dispensary that just opened in Great Barrington, has been seeing between 40-minute and 90-minute lines for entry. The randomness of the people standing in line rivals that of the DMV, without any commonalities between each person (besides the obvious fact that they want some weed). The place itself is like a wellness spa in a strip mall. Great Instagram-worthy displays and seating options abound, and after you check in with the front desk, you are ushered into the room where it all happens. Think of a bank, where you stand in line to wait for a teller, but instead of money you are getting ganja. There’s a four-page menu for you to peruse beforehand, but the weed tellers will also help answer any of your questions. From edibles to oils to pens, there’s a lot to digest. (For instance: regular old weed is now called “flower.”) Even if you aren’t into cannabis culture, you should stop through here, if only because it is a piece of history. Think of those first people to step into a bar after Prohibition. This feels like what I imagine that did: a sort of sci-fi, very strange setting where everyone is laughing. There are limits on how much of each thing you can buy, and of course, you can’t take it with you over state lines. So remember how I said Rubiners should be your first stop of the weekend? I lied. This really should be your very first stop. Theory Wellness, 394 Stockbridge St., Great Barrington.

For folk music fans, Arlo Guthrie’s community center is worth a visit. Photo: Guthrie Center

Guthrie Center

Although I haven’t been, I would regret not recommending the Guthrie Center at the old Trinity Church. The center was founded by Arlo Guthrie and acts as a community center, offering talks, free yoga and (of course!) music. There are performances most weekends through the summer and the fall and also year-round interfaith services in the church that are “BYOG: Bring Your Own God.”  Guthrie Center, 2 Van Deusenville Rd, Great Barrington, MA. 

3 Responses

  1. Brian Tobin -

    Be sure to stop in our little town of Mount Washington in the southwest corner of MA on the NY/CT state line. You’ll see the highest waterfall in the state and take a brief hike along the Appalachian trail before heading down to Great Barrington (20 minutes) and all that wonderful town has to offer!

  2. James -

    Berkshire Roots is another spot to check out in Pittsfield, you can order online before and the lines don’t sound as bad. It’s a nice spot with a cool vibe.


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