If you’re looking for how to get to the Berkshires, there are lots of transportation options available to you! The Berkshires are one of the loveliest places to visit in New England, and the towns here are a great place to visit year-round.
In this guide, we’ll go over the different areas in the Berkshires and the different ways to get to the Berkshires — from Boston, from New York City, and other destinations.
Whether you’re coming to the Berkshires for the outdoor activities, the musical performances, the art museums, or the quaint villages, you’re going to love it here.
Where are the Berkshires, exactly?
The Berkshires consist of the entirety of Berkshire county, the westernmost county in Massachusetts, next door to New York State. Not all of Western Massachusetts is part of the Berkshires, but all of the Berkshires are part of Western Mass.
Pittsfield is the largest city in the Berkshires, with a population of about 43,000. And while there’s plenty to do in Pittsfield, some of the more popular towns in the Berkshires worth visiting are Stockbridge, Lenox, Great Barrington, and North Adams.
The Berkshires is quite a large region — driving from Bash Bish Falls in the southwest to North Adams in the north would take you 90 minutes. For this reason, many Berkshires visitors like to base in one region and take day trips.
Most people drive to the Berkshires; while there is public transportation to the Berkshires, it’s very limited within the Berkshires, and you’ll have a much easier time with a car.
Within the Berkshires, there are three roughly divided sections: North, Central, and South.
North
The northern part of the Berkshires includes cities like North Adams, Williamstown, and Pittsfield.
North Adams is a former mill town that reinvented itself as an artistic haven. Today it’s home to Mass MoCA, the Massachusetts Museum of Contemporary Art, as well as Natural Bridge State Park, home to North America’s only natural white marble arch.
Williamstown is a tiny, immaculate college town, home to Williams College. Here you can enjoy the outstanding Clark Art Institute with its stunning Impressionists collection, and the town hosts the Williamstown Theatre Festival during the summer.
Pittsfield is the largest city in the Berkshires, but still not THAT big. and home to the Berkshire Museum, Hancock Shaker Village, the Pittsfield State Forest, and Herman Melville’s home Arrowhead.
Central
The central part of the Berkshires is home to some of the top activities in the Berkshires region, and is a perennially popular part of the Berkshires to visit. Some of the popular towns here include Stockbridge, Lenox, and Lee.
Stockbridge is one of the most beautiful towns in the Berkshires, filled with well-maintained historic homes and a lovely downtown. It’s home to the outstanding Norman Rockwell Museum, Berkshire Botanical Garden, historic homes like Naumkeag and Chesterwood, and the historic Red Lion Inn.
Lenox is most famous for being home to Tanglewood (the summer home of the Boston Symphony Orchestra) and world-famous Canyon Ranch Spa, but it also has cool historic homes like Ventfort Hall and Edith Wharton’s The Mount, as well as the Pleasant Valley Wildlife Sanctuary.
Lee is a low-key town known as “the Berkshires on a budget” and has some of the cheaper accommodation around. Here you can shop at the Lee Premium Outlets or head to October Mountain State Forest, the largest state forest in Massachusetts.
South
The southern part of the Berkshires is home to towns like Great Barrington.
Great Barrington is a small town that feels like the Brooklyn of the Berkshires, home to one of the best Main Streets around, the Housatonic River Walk, and lots of cool shops and boutiques. It’s also home to Monument Mountain, one of the great Berkshires hikes.
How to Get to the Berkshires by Car
Most people road trip to the Berkshires by car, including from New York and Boston. This is a very pleasant way to explore the region — there’s nothing like driving around the rolling hills, stopping at apple orchards and coffee shops, enjoying the rural atmosphere!
No matter whether you start from, you’ll probably end up on I-90 (the Massachusetts Turnpike). This is a toll road.
The exits that you want are either Exit 2 in Lee, which is the heart of the Berkshires. From here you’re close to Stockbridge and Lenox. From here you can head north to Pittsfield, North Adams, and Williamstown, or south to Great Barrington.
Know that the Berkshires are at their busiest during the summer months. Many Bostonians and New Yorkers leave for the Berkshires on Friday afternoons, coming back on Sunday afternoons, and endure a ton of bumper-to-bumper traffic as a result.
Even timing your trip to be a day earlier or later is a good way to miss out on the worst of the traffic.
How to Fly to the Berkshires
The closest airport to the Berkshires is Albany International Airport in Albany, New York. Albany Airport is about a 50-minute drive from Stockbridge.
Alternatively, Bradley International Airport in Windsor Locks, Connecticut, close to Hartford, is another close airport to the Berkshires. Bradley is about an 80-minute drive from Stockbridge.
Both Albany and Bradley have nonstop flights to destinations throughout the Eastern US with a few further-flung destinations as well.
Further afield, you have Westchester Airport in White Plains (2 hours from Stockbridge), Logan Airport in Boston (2.5 hours from Stockbridge), and the New York City airports: JFK, LaGuardia, and Newark (each about 3 hours from Stockbridge).
We recommend checking flights on Skyscanner to find the best prices.
If you’re flying private (look at you, moneybags!) there are a few airports in the Berkshires: Harriman-West Airport in North Adams, Great Barrington Airport in Great Barrington, and Lyon Aviation in Pittsfield.
How to Get to the Berkshires by Bus
Several bus lines give you easy access to the Berkshires. If you’ve traveled in Massachusetts by bus, you’re undoubtedly familiar with Peter Pan Bus Lines, and Greyhound Bus Lines run buses to the Berkshires as well.
Peter Pan buses run from Boston to Pittsfield via Springfield. Check their website for the latest schedules.
Greyhound runs buses from Boston to Lee and Pittsfield. Check their website for the latest schedules.
If you’re coming from New York, things are a bit more complicated. Bus websites will try to route you through Boston (yuck). Your best option is to take a bus from New York to Albany and switch to a Greyhound bus to Pittsfield.
How to Get to the Berkshires by Train
Believe it or not, you can get to the Berkshires by train, too! Pittsfield is an Amtrak stop on the Lake Shore Limited line.
The Lake Shore Limited has two arms — from Boston to Chicago, and from New York to Chicago — which join up in Albany.
That means that you can take the train directly from Boston to Pittsfield (or from Chicago or Cleveland to Pittsfield, if you’d like!) but if you come from New York, you’ll need to get off in Albany and switch to rail service going in the other direction.
Because it’s Amtrak, trains don’t run often — only once per day — so be sure to check the schedules before you book.
However, there’s another great option — the Berkshire Flyer! The Berkshire Flyer is an Amtrak train from New York to Pittsfield via Albany that runs seasonally from July through September.
The train leaves New York on Friday afternoons and makes the return trip from Pittsfield on Sunday afternoons.
This is a very popular way to get to the Berkshires from New York City, so be sure to book early if you want to take this train journey. Bookings open in March and you can learn more here.
How to Get to the Berkshires from Boston
You have four ways to get from Boston to the Berkshires:
Option 1: Drive. This should take around 2.5 hours if there isn’t much traffic, depending on where you’re going.
Option 2: Bus. The bus from Boston to Lee takes about 3 hours and 15 minutes, and it takes another 30 minutes to Pittsfield from there.
Option 3: Train. The train from Boston to Pittsfield takes about 3.5 hours.
How to Get to the Berkshires from New York
You have four decent ways to get from the Berkshires from NYC:
Option 1: Drive. It’s around a three- to four-hour drive depending on where you’re located in the city.
Option 2: Train. Take the Berkshire Flyer to Pittsfield Train Station on Fridays and Sundays, July through September (four hours).
Option 3: Bus. Take a bus to Albany (three hours), then switch to another bus to Pittsfield (one hour).
Option 4: Train and bus combination. Take any of the trains to Albany-Rensselaer Station (2.5 hours), then take a bus to Pittsfield (one hour).
How to Get Around the Berkshires
Again, the best way to get around the Berkshires is by car, because public transportation is extremely limited. There are cab companies if you need them, but Ubers are very few and far between.
That said, there are bus routes between different towns in the Berkshires. You can check current bus schedules on Berkshire Rapid Transit Authority.
And if you need to rent a car upon arrival, there’s an Enterprise car rental in Pittsfield.
More on the Berkshires:
Have you been to the Berkshires? How did you get there? Share away!
