The Berkshires is calling your name with its breathtaking landscapes, vibrant culture, and farm-fresh cuisine. Whether you’re dreaming of a peaceful weekend retreat, planning an extended two-week escape, or even considering making this dynamic region your new home, our 30 charming towns and two welcoming cities are eager to embrace you. Come and experience the warmth and beauty that await your arrival—each community ready to share its unique stories and spirit with you. Your journey toward serenity, creativity, and connection starts here in the heart of the Berkshires.
Getting from Boston to the Berkshires
Travelers from Boston have a variety of options to reach the serene landscapes of the Berkshires. If you enjoy the freedom of the open road, a scenic drive will take you there in about 2.5 hours—perfect for those who love to meander through picturesque New England towns. Prefer to sit back and relax? Hop on a Peter Pan or Greyhound bus, and you’ll arrive in Pittsfield in around 3.5 hours. For a touch of nostalgia, consider the Amtrak Lake Shore Limited, which offers a 3.5-hour train journey that lets you watch the countryside unfold as you journey toward tranquility.
Getting from NYC to the Berkshires
If you’re traveling from New York City, the Berkshires offers several delightful travel options. From July to September, you can embark on a scenic 4-hour journey aboard the Berkshire Flyer, an Amtrak service that lets you unwind and soak in the views, departing on Friday afternoons and returning Sunday. For those traveling year-round, driving is a convenient option, with a 3-4 hour drive that takes you from the bustle of the city to the peace of the countryside. Bus services from Peter Pan or Greyhound bus are also available, though they require a transfer in Albany, making it a 4-5 hour trip. For an adventure that combines different modes of travel, you can take a train to Albany-Rensselaer Station and continue by bus to Pittsfield.
Arriving via Airport
For those flying in, the Berkshires is within easy reach of several airports. Albany International Airport, just 60 minutes away, is the closest major hub, offering a quick gateway to the region. Bradley International Airport in Connecticut is another convenient option, located about 80 minutes from the Berkshires. If you’re arriving from further afield, Boston’s Logan International Airport and New York City’s airports (JFK, LGA, EWR) are viable options, though you’ll need to plan for a longer drive to reach your destination. For a more personalized arrival, private jet and plane options are available at smaller local airports like Harriman-West in North Adams, Lyon Aviation in Pittsfield, and Great Barrington Airport.
Local Transportation Tips
Once you’re in the Berkshires, the best way to explore is by car, giving you the flexibility to wander at your own pace. While public transportation is limited, the Berkshire Regional Transit Authority (BRTA) provides bus services connecting major towns and attractions—ideal if you’re looking to explore without driving. Rental cars are available from Enterprise in Pittsfield, offering a convenient way to dive into your adventure. For a more eco-friendly option, consider renting a bike from a local shop—there’s no better way to experience the breathtaking landscapes and charming towns up close. Taxi services and limited ride-sharing options are also available in some areas, ensuring that you can get around with ease.
