2 Days in the Berkshires, MA: An Easy Weekend Getaway from NYC
A glass of wine and a view at Balderdash Cellars in Richmond, MA.
This was my first time in the Berkshires, and after two days there, I understood the appeal immediately. It's close enough to NYC that you don’t spend your entire weekend getting there, and once you're there, you’re immediately surrounded by beauty and a different pace.
Here's exactly where I went over two days, in the order I experienced them in. It's not the only way to see the Berkshires, and definitely not everything the region has to offer. But it's a varied, unhurried mix of indoor and outdoor activities I really enjoyed, and I think you will too.
Planning Your Trip
Getting there from NYC
The Berkshires are roughly a 3-hour drive from New York City, which is part of what makes it an easy weekend option rather than a full weekend of driving. Leaving early morning on a Saturday and heading back Sunday afternoon is enough time to cover the two days above without feeling rushed. I packed everything for the weekend in my (gifted) Incase A.R.C. Duffle, which held up perfectly for a quick trip like this, with just enough room for clothes and small equipment.
Where to stay
Lenox and Stockbridge are both good home bases if you want to be centrally located to everything in this itinerary.
Best Time to Go
There's something to do in the Berkshires in every season. I went in late summer for this itinerary, but know there are plenty of outdoor and cultural activities that take place then, like the summer concert season at Tanglewood. Fall is absolutely beautiful, but expect foliage crowds (still worth it in my opinion). If you're going in winter, this itinerary shifts: swap the garden and orchard for a day at Bousquet Mountain in Pittsfield, a smaller, family-friendly ski area that fits the same low-key pace as the rest of this trip.
Day 1: Art, Wine, and a Walkable Small Town
The Clark Art Institute (Williamstown)
My first stop was the Clark Art Institute. There's a reflecting pool near the entrance, and installations spread across the walking trails and meadows before you even get inside. The museum itself covers Renaissance through Impressionist work, and I could've easily spent half a day there.
MASS MoCA (North Adams)
A few minutes away in North Adams, MASS MoCA is the opposite of the Clark. It's a former textile mill, now one of the largest contemporary art museums in the country. Where the Clark is quiet, this is loud in the best way, and having both in the same morning gave the day some real range.
Balderdash Cellars (Richmond)
By early afternoon, I wanted to slow down, so I stopped at Balderdash Cellars. The views were spectacular; you could walk right through the vines, the wine was good, and the whole place had this lively energy.
Downtown Lenox
Before it got dark, I explored downtown Lenox. It's small, walkable, and cute, with little shops, great restaurants, and an idyllic feel that makes it easy just to wander. There's even a bookstore that doubles as a wine bar called “Get Lit.”
Dinner AT MINT Indian Lakeside Dining & Bar
I found an Indian restaurant near downtown Lenox, in Lee, right on Laurel Lake with great sunset views, called Mint Indian Lakeside Dining & Bar. The food was excellent, and so was the service. Two things worth noting: it’s located inside the Black Swan Inn, and they have a Sunday buffet.
Where I Stayed: Berkshires Untold
I ended the night checking into Berkshires Untold. Built as a motor lodge in the 1970s, it has since been reimagined into a modern space with vintage charm. The club room was the perfect spot to grab a cocktail before heading out to the fire pit to sit under the stars.
Day 2: Coffee, Gardens, and an Orchard
No. Six Depot (West Stockbridge)
Day two started at No. Six Depot, an old train depot turned coffee shop and roastery in West Stockbridge. They roast the beans on-site, sourced from small farms around the world.
Downtown Stockbridge
Stockbridge itself is the postcard version of a classic New England town, and it's worth slowing down for even if you're just passing through. Norman Rockwell lived here, and Main Street is the same one he painted for his famous 1967 illustration, so it's worth strolling even if you're not stopping in the shops.
Berkshire Botanical Garden
Berkshire Botanical Garden was one of the stops I was looking forward to the most. You can take your time walking through at your own pace, and there's a self-guided audio tour app you can use on your phone if you want more context as you go.
Hilltop Orchards
My last stop was Hilltop Orchards. You can pick your own apples or just shop the farm store, and I couldn't leave without a few of their signature cider donuts to bring home.
Would I Go Back?
A quiet moment on the water that was worth pulling over to take in.
By the time my two days wrapped up, I felt like I'd gotten a real mix of what the Berkshires has to offer: fascinating museums, wine with a view, walkable downtowns, dinner on a lake, fresh coffee, a botanical garden, and an orchard stop. None of it felt rushed, and most of all, it felt easy.
What stuck with me most is how much range fit into so little time. I didn't plan around a single theme, and that variety is exactly what made it feel like a getaway instead of a checklist. A next visit would likely look completely different, since I only scratched the surface of what's here, and that's part of the appeal. If you're weighing whether the Berkshires is worth a weekend from NYC, this itinerary is my answer: yes, easily, and you won't need more than two days to feel like you actually got away.
FAQ’s
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It's enough for a solid first taste, especially if you pick a mix like this one: a couple of museums, one winery, a small town, and one nature or farm stop. You won't see everything, but you won't feel like you're rushing either.
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About 2.5 to 3 hours by car, depending on where in the Berkshires you're headed and traffic out of the city.
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Yes. The towns are walkable once you're in them, but the stops themselves (Williamstown, North Adams, Richmond, Lenox, Lee, West Stockbridge, Stockbridge) are spread across the region, so a car is the only practical way to link them together.
✧ For the intentionally curious traveler - pass it on.
More weekend getaways from NYC to New England:
Why Rockport, MA Is the Best-Kept Secret on the New England Coast
A Charming Weekend Summer Escape in Rhode Island: Narragansett and Block Island
Karen Gomez
I'm a NYC-based travel writer, photographer, and the founder of Passport in Photos — for those who want to feel somewhere, not just see it.