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5 Reasons to Hop on Board the Berkshire Flyer This Summer

Posted on May 09, 2023Written by 1Berkshire Marketing Team
Updated on May 06, 2024

Craving a weekend away in the Berkshires – but dreading the stress and hassle of driving there from the city? This summer, there’s a better way.

Catch the Berkshire Flyer and relax in comfort from New York’s Penn Station all the way to Pittsfield, MA, in the heart of the Berkshires.

Spend four hours napping, watching a movie, planning your trip, or taking in the scenery of the Hudson River Valley – not worrying about traffic on the Thruway. Starting June 21st and running each weekend through Labor Day, the Berkshire Flyer is the ideal way to reach this idyllic region of Western Massachusetts.

Read on for the must-see summer spots, plus a few pro tips to help you have a hassle-free visit.

Before you go:

  • Tickets for the Flyer are on sale now! Book early to guarantee yourself a seat.
  • Consider upgrading to business class for more flexibility, a fully refundable ticket, plus complimentary nonalcoholic drinks on some trains.
  • Planning a visit for Memorial Day or Labor Day weekend? Those are the only two weekends when you’ll get two full days and three nights in the Berkshires.
  • While you don’t need a car to get to the Berkshires, you’ll want one once you arrive. Make advance plans to rent (or hire) a car!
  • For the first time this year, the Berkshire Flyer now includes train service from New York City to Pittsfield on Sunday mornings!

5 things you won’t want to miss during your weekend in the Berkshires

You could spend every weekend in the Berkshires all summer and still not experience everything the region has to offer. To help you plan your next trip, we’ve narrowed it down to five themes highlighting the best of the Berkshires – and you can get there from NYC on the Berkshire Flyer!

The cultural experiences

The performing arts abound in the Berkshires so once you’ve gassed up your rental car, head toward the center of the Berkshires for a show at Tanglewood. For the full experience, pick up a bottle of wine at Dare Bottleshop & Provisions in Lenox, some local cheese from High Lawn Farm in Lee and freshly prepared picnic fixings or pizza from Guido’s Fresh Marketplace in Great Barrington or Pittsfield. Don’t forget a picnic blanket and some candles.

To the north, there’s MASS MoCA in North Adams – one of the country’s largest centers for contemporary visual and performing arts. Little ones will love the Kidspace, and grown-ups will love the performances. This summer, you can catch The Pixies & Modest Mouse, comic Ilana Glazer and more.

For dance lovers, Jacob’s Pillow in Becket can’t be missed. Watch dance shows from around the world in a setting that’s equally stunning.

The outdoor thrills

Craving a weekend filled with adrenaline? Fly to the Berkshires by rail service to string together the most exciting outdoor adventures, starting with the two-hour zipline tour at Catamount Mountain Resort. At over a mile long, the final zipline – dubbed the “CataMonster” – is the longest in the contiguous US.

Let your heart rate return to normal, then explore on your own two feet. Climb Mount Greylock if you’re feeling ambitious, or choose Parsons Marsh for a more accessible hike. Been there, hiked those? Find other, less traveled trails. Prefer rapids over trails? Book a half or full-day whitewater rafting trip with Crab Apple Whitewater. You’ll ride the Flyer back to the City refreshed!

Tanglewood Music Festival, credit Fred Collins

The history and education

If you’re a history buff, the Berkshires is your playground. Plan your weekend around a museum hop, beginning in Williamstown with the Clark Art Museum. This rare gem is both an art museum and a research institution. Start with the outdoor sculpture exhibits, wander the grounds, then visit the Manton Study Center for Works on Paper – to see how many of the more than 6,500 prints, drawings and photographs you can view in one visit. Head south to Lenox where you can take a guide tour at the Berkshire Scenic Railway Museum’s Lenox Station – perfect for train enthusiasts, especially after riding the Berkshire Flyer. From there, visit Hancock Shaker Village, a working farm and living history museum dedicated to life in early New England. Go early so you don’t miss the baby animals! Finally, wrap up your tour at the Norman Rockwell Museum in Stockbridge with an impressive collection of illustrations from Rockwell and other American artists.

The culinary adventures

Plan a foodie weekend or squeeze in a few local hot spots between your other adventures. For drinks and live music, head to the Lion’s Den at the famous Red Lion Inn (a Berkshire institution). Their wine list offers 300-plus choices and is a perennial award winner.

Satisfy your sweet tooth with handmade European-style chocolates at Chocolate Springs Cafe in Lenox, feel like a kid again at Robin’s Candy Store in Great Barrington or get to Shire Donuts in Dalton bright and early for fresh, hot donuts made while you watch. Whatever your confection of choice, buy a treat for the sweet ride home on the Flyer!

Book a night in Sheffield to sample the best of the region’s beer and spirits. Start with small-batch tastings and flights at Berkshire Mountain Distillers, or sip on a rotating roster of craft beers at Big Elm Brewing. Up north, check out the modern, creative craft brews at Bright Ideas Brewing in North Adams.

Craving a caffeine boost? The coffee scene is big in the Berkshires.

The wellness services

After all that activity, wind down with a visit to any of the luxury day spas and retreats in the area. For door-to-door service, book with Miraval Berkshires – they will coordinate direct pick-ups and drop-offs if you take the Flyer. Or choose the equally renowned Kripalu Center for Yoga & Healing or Canyon Ranch. No matter where you unroll your yoga mat or book a massage, you’ll end the weekend relaxed and rejuvenated.

After you have packed in a fun-filled weekend in the Berkshires, simply get on board the Berkshire Flyer and take the relaxing train ride back to the city. Just one trip to the Berkshires will most likely not satisfy, so think about buying train tickets for multiple weekends to ensure you get your “Berkshire fix.”

For more world-class summer travel ideas in the Berkshires, visit Learn more about visiting Massachusetts at

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