The Berkshires

Where to stay

Great Barrington is the best base in the region and, arguably, the best walkable downtown in eastern ski country. Main Street runs a few hundred yards of restaurants, a co-op grocery, a bookshop and the Mahaiwe theatre, and you can do a whole evening on foot. Butternut is five minutes east on Route 23 and Catamount about fifteen minutes west. The cost is that Jiminy Peak, the region’s biggest mountain, becomes a forty-five-minute drive, and that lodging here is priced off a New York City weekend market rather than a ski market.

Lenox is smaller, prettier and more expensive. The village core is a handful of blocks around Church Street with a small market, a few good kitchens and not much else in February — Tanglewood, which is the reason most people know the name, is shuttered from September to June. Its real argument is position: it sits in the middle of the Route 7 spine, which puts Bousquet, Jiminy and Butternut all within half an hour instead of forcing you to choose an end.

Pittsfield is the cheapest base and the least charming, and for some people that is the right trade. It is a working city of roughly 43,000 with a hospital, supermarkets, a downtown on North Street with year-round theatres, and Bousquet inside the city limits. It is also the only place in the region where an ordinary weeknight looks like an ordinary weeknight rather than a closed season.

Lee and Stockbridge are the pragmatic middle. Lee sits at the Mass Pike interchange and is the easiest arrival in bad weather; Stockbridge is a two-block postcard with the Red Lion Inn and almost nothing else open late.

Jiminy Peak itself has the Country Inn and a condo cluster — the only slopeside beds in the region. Take them if ski-in convenience matters more than anything else, and understand you are choosing a resort complex over a town.

This guide covers the Route 7 spine from Pittsfield south. Williamstown and North Adams are also Berkshire County and also worth a winter trip, but they are built around MASS MoCA and a college, not around lifts, and they belong to a different itinerary.

Getting there

Driving is the honest answer. From New York City it is roughly two and a half to three hours to Great Barrington, usually via the Taconic or I-684 and Route 22, then Route 23 east. From Boston it is about two and a half hours on the Mass Pike to the Lee interchange. Albany International is the nearest airport at around an hour to Lenox; Bradley near Hartford is a little further but often cheaper into Great Barrington.

Amtrak stops at Pittsfield on the Lake Shore Limited, one train each way per day. Westbound from Boston it is scheduled into Pittsfield in the late afternoon — around 4.30pm on recent timetables — and the eastbound Boston train leaves Pittsfield around 5pm. Both are awkward: you arrive after the lifts close and you leave before they do. The Albany–Boston leg was suspended for a stretch and only resumed in December 2025, so treat it as useful rather than dependable, and check the current timetable before you build a trip on it. The Berkshire Flyer, the seasonal train from New York, runs summer weekends only and is irrelevant to a ski trip.

Peter Pan coaches serve Pittsfield’s intermodal centre, plus Lee, Lenox and Great Barrington, on New York and Boston–Springfield routings. A couple of round trips a day is the realistic picture.

Getting around

BRTA is a real bus system by rural standards and it will get you between towns. Route 921 runs Pittsfield–Lenox–Lee–Stockbridge–Great Barrington; Route 2 covers Pittsfield–Lenox–Lee and Route 21 the Lee–Stockbridge–Great Barrington end. Service is Monday to Saturday only, with the last weekday departure from the Pittsfield intermodal centre around 7.30pm and a much shorter Saturday span. There is no Sunday service.

What BRTA does not do is reach a chairlift. Not Bousquet, eight minutes from downtown Pittsfield; not Butternut, five minutes from Great Barrington’s Main Street. There is no ski shuttle, no resort bus, and nothing linking the four local mountains to each other. Rideshare exists in Pittsfield and thins out fast going south.

So the region splits cleanly. Without a car you can live well in Great Barrington or Pittsfield for a week, eat, shop and see things — and not ski. With a car the whole cluster opens up, and the driving is genuinely easy: Route 7 is a good road, and the only crossing that reliably turns unpleasant is Route 2 over the Hoosac range if you go for Berkshire East.

Who it suits

• Mixed groups where not everyone skis. The single strongest case. Two days at Butternut and Bousquet, an afternoon at the Norman Rockwell Museum, dinner on Main Street — the non-skier is not being parked somewhere.
• Families with beginners. Butternut’s learning terrain and Bousquet’s night skiing are well-suited and cheap by Northeast standards, and the drives are short.
• Weekenders from New York. Nowhere else within three hours combines this quality of town with four lift-served mountains.

It suits advanced skiers least. Catamount’s steepest pitch and a good day at Berkshire East are the ceiling, and neither will hold you for a week.

Living for a season

Be clear about this: almost nobody spends a ski season in the Berkshires, and the region gives you very little reason to. There is no ski-town labour market — Jiminy Peak is the only operation here with a hotel, and none of the areas runs the kind of employee-housing programme that makes a Vermont or Maine season financially possible. Winter is the Berkshires’ quiet season. The cultural economy that supports the region runs from May to October; the lifts are a sideline.

What the region does offer is a genuine year-round base for someone who is not a seasonal worker. Pittsfield is a real city with Berkshire Medical Center, supermarkets you can reach on foot, and Framework, a coworking space on North Street — a combination almost no ski town in New England can match. If you are a remote worker who wants to ski two days a week and live somewhere with a dentist, this works better than Ludlow or Lincoln.

Housing is the constraint. Second-home and short-term-rental demand, heaviest in south county, has tightened the long-term market considerably since 2020, and winter is when owners hold inventory back for the summer season. Budget more than the mountains would suggest, and look at Pittsfield and Dalton before assuming Great Barrington is affordable.

What the town is like

There is no single Berkshire town, which is the point. Pittsfield is a post-industrial small city still working out what it is — North Street has theatres, a museum and stretches of vacancy in the same block. Lenox is manicured, expensive and half-asleep in winter. Great Barrington is the one that feels alive year-round: an independent grocery co-op, a working cinema and theatre, and enough restaurants that some are open on a Tuesday in March. Not all of them are — expect kitchens to go dark early in the week once the holidays pass.

The thing to understand is that the Berkshires were built for summer. Tanglewood, Jacob’s Pillow and most of the festival apparatus are closed all winter. What survives is quieter and, if you came to ski, better: the Mahaiwe and the Colonial programming through the cold months, the Norman Rockwell Museum and the Berkshire Museum open year-round, and lodging at a fraction of August rates. The mountains are small. The compensation is that you are staying in a place that would still be worth visiting if they closed.