When I get the itch to escape New York City, my sights often turn to the Hudson Valley. But just three hours outside of NYC is the Berkshires, a collection of small towns and villages in Western Massachusetts. This cluster of small towns surrounded by gorgeous hillsides filled with all the art, food, and nature you desire for a 3-day weekend getaway!
A long weekend in the Berkshires has something for everyone from the foodies, to the outdoorsy types, to the and of course the artists and artists at heart. This is how I suggest spending three days there to get the best of all sides of the Berkshires.
Where to Stay in the Berkshires?
The Berkshires stretch up the entire Western side of Massachusetts. It takes more than an hour to drive from North Adams down to Great Barrington (the Northern and Southern extremes of the area). In order to be able to see it all in one weekend, I suggest staying somewhere that is central. Both Lenox and Pittsfield are central towns with enough dining and activities to keep you busy while using them as a home base. I stayed at the Hotel on North in Pittsfield.
Friday – Arrival and Check in
Hotel on North – Pittsfield
The Hotel on North allows small dogs (like Chewy, above!) and check in is a breeze. Take some time to relax in your room decorated with local art, or the comfy lounge before departing for dinner. The hotel itself is a great option for pre-dinner drinks. Staff will make one of their own craft cocktails or bring a local beer to you in your room or any public area of the hotel. (Hotel on North has its own highly rated restaurant but due to COVID it was closed when I visited.)
The rooms here are big enough for a small seating area to enjoy your cocktail with your dog in her bed at your feet as well as a large bedroom area. If you’re traveling with a pup, this is a win!!
There is a large common area on the second floor with multiple seating areas, coffee table books, and board games. It’s a great place to unwind after a day of hiking or to jump into a competitive game of Scrabble.
Even without the hotel restaurant open there are plenty of bars, cafes, and restaurants along Pittsfield’s main street just a couple minutes walk away.
33 Main – Lenox
33 Main is part bed and breakfast, part luxury hotel. I was attracted to the amenities like the included breakfast and pretty interiors. This hotel also offers dog friendly rooms. Just like any hotel I would consider, it’s within walking distance of many bars and restaurants.
Where to Grab Dinner in the Berkshires
I’m all about a walk after a day of travel rather than getting back in the car. So both of these restaurants are less than a 10 minute jaunt from the hotel. The perfect stroll to get some fresh Berkshires air on your face without feeling too daunting as a return trek.
District Kitchen & Bar – Pittsfield
This is a contemporary gastropub, so it was right on the top of my list. They have classic gastropub fare like mussels and chicken liver mousse plus creative dishes like a kimchi burger so both the adventurous and the not-so-adventurous can find something to their liking on the menu.
Since you just got to the Berkshires be sure to give the local beer a try. The menu at District has the location of each brewery denoted so you can see just how “local” you’re ordering. I suggest Big Elm brewery if they have it available!
Bistro Zinc – Lenox
It’s always fun to feel a little fancy on the first night of vacation, but still casual enough to be comfortable after a day of work. Bistro Zinc strikes this perfect balance. This bistro has French classics like steak frittes and French onion soup alongside comfort foods including burgers and curries.
After finishing dessert you can head back to the hotel for a good night’s rest before you explore the area…or move to lively bar at Bistro Zinc to chat with locals and try the barkeep’s recommendations.
Saturday – A Fancy Day in the Berkshires
There are two sides of the Berkshires: the nature and small town feel or the extravagant resorts and cultural and historical institutions. Today we’re discovering our elegant side.
Crepes and Art at Starving Artist
Start the morning light with a sweet or savory crepe at Starving Artist. The crepes are tantalizing but the real draw is lingering over tea in the connected gallery that displays local artists. The space is large and airy with tons of natural light falling on the paintings and sculptures.
Early Dinner at Red Lion or Blantyre
There’s nothing especially stylish about a 5pm dinner, but these two locations are certainly beautiful in the daylight. A sunset dinner in the Blantyre’s intricate solarium is unforgettable. Light bounces off the antique crystal and glass chandeliers and the view of the forests of the Berkshire hills. The menu at Café Boulud at the Blantyre is pretty standard for a Boulud restaurant with things like filet mignon, duck confit, and cauliflower veloute.
The Main Dining Room at the Red Lion Inn leans more charming than the grandiose atmosphere at the Blantyre. The menu is rustic while still being upscale with items like braised pork shank and traditional prime rib service. For the enophilies the wine list features more than 30 bottles.
Since you’ll arrive when it’s still light out take a walk around the grounds of the inn and if there is time enjoy a tea or a cocktail in the outdoor courtyard.
After an early dinner head back toward the hotel and park the car! Then enjoy a night cap at a walkable bar or sip a tea with some dessert.
Methuselah Bar – Pittsfield
Eventually this bar will get a post of it’s own because it is simply perfection. Plenty of little corners for hushed conversations to end a romantic night as well as a bright and occasionally boisterous main bar for those that prefer to socialize with their drinks. The cocktail list is creative and extensive but of course the bartenders can also make any classic drink requested. The are at least half a dozen beers on tap that are well curated to feature classics as well as local brews and there are also special beers offered by the bottle. I couldn’t refuse a 750ml of La Fin Du Monde.
If you’re visiting for dessert I highly recommend the goat cheese cheesecake, I think I gushed to the bar owner Yuki about how much I enjoyed the perfect balance between sweet, tart, and savory for at least three minutes.
Brava – Lenox
Quiet and quaint Brava feels intimate as soon as you walk in. If your appetite comes back after such an early dinner the oysters or charcuterie board as light but still satiating. Wines are a specialty but beer and cocktails are also available. I suggest a negroni with a cheese board for the perfect end to a luxe day.
Sunday – Visit a Museum and a Brewery
Mass MOCA (the Massachusetts Museum of Contemporary Art)
On of the biggest draws in North Adams is Mass MOCA. The massive museum one of the largest centers for contemporary visual art and performing arts in the United States. The exhibitions are ever changing and especially in the busy summer and “leaf peeping” (aka fall) seasons it is best to book your tickets online in advance. Tickets are timed so you can plan the rest of the day around your museum slot.
Bright Ideas Brewery in North Adams
Bright Ideas is located on the campus of Mass MOCA, a perfect place to relax after exploring the expansive museum. It’s a big open casual taproom with plenty of light and friendly vibes. If you’re hungry barbecue from the shop next door can be brought in.
Bright Ideas makes a variety of classic beer styles, and I thought their dark beers were especially well done. Possibly inspired by the wealth of art just a few feet away, Bright Ideas has thoughtfully designed posters for each beer release. Check them out while you enjoy a local craft beer.
Beyond giving you an excuse for a pint after all that art, Bright Ideas is near Greylock Works, a warehouse spacing housing a cidery, distillery, and great little restaurant to boot. The Distillery at Greylock Works is one of those magical little stops that only exist in these smaller towns, an artisan crafting something beautiful hidden away. I highly suggest a visit!
The Norman Rockwell Museum
Stockbridge, Massachusetts in Norman Rockwell’s hometown. His eponymous museum located there displays not only a rich collection of his art, but also his personal memorabilia. The art doesn’t end inside the museum but also extends to sculpture throughout the grounds.
If you’d like to spend a full day at the museum that is definitely possible, especially as there is a restaurant where you can enjoy lunch on the outdoor terrace.
Tickets can be purchased online or walk up. If you’d like to take a guided tour I suggest booking in advanced.
Hilltop Orchards Cidery
Just about 15 minutes from the Norman Rockwell Museum is Hilltop Orchards. The Hilltop team makes hard cider using local apples. Some of the trees in their orchard are more than 100 years old.
Hilltop offers both guided tastings and full guided tours. They are proud of their artisanal cidermaking process which you can learn about on a tour or through chatting with enthusiastic staff.
Breweries in Greater Barrington, Sheffield and Southern Berkshires
I already suggested Big Elm’s beers but you can experience the very best of the selection at the brewery. It is a bit of a drive from Lenox or Pittsfield but the good news is the drive is scenic cutting through the rolling hills.
A little closer than Big Elm in Sheffield is Barrington Brewery & Restaurant in Greater Barrington. The brewery is close to several parks including Monument Mountain Reservation where you can hike or bird watch before a filling lunch at the brewery.
Monday – Breakfast and Bon Voyage to the Berkshires
Alas, three days goes fast in such a picturesque location. Best to stop somewhere local for a hearty breakfast before you hit the road.
Dottie’s Coffee Lounge – Pittsfield
Dottie’s is beloved throughout the Berkshires for the homey atmosphere paired with excellently crafted breakfast fare. Be careful! This spot is so popular they sometimes literally run out of food. The location is spacious with many people taking their bagel sandwiches and mochas to-go so even with the popularity it’s not likely you’ll need to wait.
Bagel & Brew – Lenox
Lenox Coffee is a solid stop for a morning bite, but I’m partial to the bagel shop that has a beer garden. Bagel & Brew has bagels and sandwiches that can be customized (but I go for the classic lox on an everything). If you’re more into brunch than a quick breakfast there’s a selection of special beers to complete the meal. Check the hours before you visit, they are often closed from 12pm to 3pm.