Ultimate Guide to Western Massachusetts

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Since the Gilded Age, the Berkshires of Western Massachusetts (Western Mass) have provided a city escape for New Yorkers- wealthy Gilded Age tycoons built summer mansions there, and the Berkshires were inundated with wealthy socialites. There is good reason for it, too. Western MA is filled with gorgeous scenery loads of outdoor activities, and, through the years, has brought several attractions that make the allure even more powerful.

I spent the summer in the Berkshires years ago, doing an apprenticeship at the Berkshire Theatre Festival (now the Berkshire Theatre Group). I got to experience the Berkshires at their finest. I also lived in Western Mass for several years, in Hampden County, east of the Berkshires. Most recently, I visited the Berkshires and Western Mass for the first time as a tourist and was excited to see all it has to offer through the eyes of a tourist. 

What Is Considered Western Mass? 

Before I delve into all of the wonderful things that Western MA offers, let’s go through what (or where) Western MA actually is. Western Mass is anything west of and including the city of Springfield. This is a giant chunk of the state, and to say there is much to see and do would be an understatement. The counties included are: 

• Berkshire County
  Renowned for its stunning scenery, the Berkshires are home to charming towns, world-class art at the Clark Art Institute, and cultural landmarks like Tanglewood and the Norman Rockwell Museum.

• Franklin County
  Featuring the Deerfield River Valley and the Mohawk Trail, this county offers outdoor enthusiasts a range of activities, from hiking and biking to kayaking and fishing.

• Hampshire County
  Home to college towns like Amherst and Northampton, Hampshire County boasts a vibrant arts scene, historic sites, and a thriving culinary scene.

• Hampden County
  As the largest county in Western Massachusetts, Hampden County offers a mix of urban amenities in Springfield and rural charm in its surrounding towns.

How to Get to Western Mass

Western Massachusetts is easily accessible by train, plane, bus, and car. 

Flying to Western Mass

Bradley International Airport in Connecticut is about twenty minutes from Springfield and an hour to the Berkshires. The Albany, NY, airport is an hour from several Berkshire hotspots. Public transportation is available from the airport to the bus and train stations, where you can book a bus or train to your Western Mass destination. 

Train

Springfield has an Amtrak station, which offers direct rides to several Northeast cities and connects train rides all over the US. Pittsfield, Holyoke, and Greenfield also have Amtrak stations. 

Driving to Western Mass

Major highways, such as Interstate 91 and Interstate 90, connect the region to other parts of the state and beyond.

Things to Do in Western Mass

Outdoor Activities

Hiking

There are several opportunities for hiking, including Mount Greylock, the highest peak in Massachusetts. Mount Tom, located in Holyoke, offers stunning views of the Connecticut River Valley. Northfield Mountain offers 26 miles of trails for biking and hiking and special events like Hiking and Yoga, which involve hiking with breaks for yoga poses. 

Other popular hiking spots include: 

• The Berkshires 
  Beyond Mount Greylock, explore the diverse terrain of the Berkshires. The Appalachian Trail offers challenging hikes with stunning vistas. Consider day hikes or multi-day backpacking adventures.
• Taconic Mountains
  Venture into the Taconic Mountains for a less crowded experience. Discover hidden waterfalls, rocky peaks, and peaceful trails.

Skiing and Snowboarding 

Western MA has its share of skiing and snowboarding spots during the winter months. You can hit the slopes at Berkshire East, Jiminy Peak, Butternut Ski, and more for some winter fun.

Kayaking, Canoeing and Paddleboarding

Loads of smaller lakes and rivers are perfect for kayaking and canoeing; of course, the Connecticut River offers plenty of opportunities for water sports. Companies like Paddle N’ Party in South Hadley have single-person and tandem kayaks, paddleboards, and Hydro-Bikes available for rental. Spots perfect for paddling include Lake Wyola in Shutesbury and Aldrich Lake in Granby, which prohibits motorboats, so you’ll have a genuinely peaceful adventure. Further west, you’ll find Stockbridge Bowl, Lake Mansfield, Pontoosuc Lake, and more. 

Cultural and Historical Attractions

Western MA is chock-full of cultural and historical attractions to check out during your stay.  

You can see world-class art in a stunning setting at The Clark Art Institute in Williamstown. Get a glimpse into Americana and explore the life and work of Norman Rockwell at the Norman Rockwell Museum in Stockbridge. You can explore Historic Deerfield, comprised of twelve preserved houses dating from 1730 to 1850, to get a real glimpse into New England life in the 18th and 19th centuries. Wistariahurst, in Holyoke, is a Victorian mansion with public gardens, house tours, an art gallery, and special events throughout the year. You don’t have to head to a big city to check out some of the best up and coming art- just head to the Massachusetts Museum of Contemporary Art (MASS MoCA), in North Adams. 

Western MA is not without its choices for music and theatre either, especially during the summer months. World-renowned Tanglewood brings top performers to the Berkshires every summer and is the summer home to the Boston Symphony Orchestra. Summer theatre includes the Berkshire Theatre Group,  Williamstown Theatre Festival, and Shakespeare and Company – all in the Berkshires. Check out a play or musical at The Majestic Theatre in West Springfield; Happier Valley Comedy provides gut-busting performances in Hadley if you’re looking for laughs.  

Dance lovers will be enthralled by performances at Jacob’s Pillow, a National Historic Landmark that delivers award-winning dance performances. 

Wellness in Western Massachusetts

The Berkshires is home to two of the most well-known wellness resorts, Canyon Ranch and Mirival, both providing guests with all-inclusive wellness by means of healthy eating, mindfulness, spa treatments, and fitness. Western MA visitors can take a yoga class at Kripalu, relax in a hot tub at Elements Hot Tub Spa in Amherst, or enjoy salt therapy at 

Things to Do in Western Mass With Kids

There is plenty to do in the area for kids, including two museums dedicated to beloved children’s authors; the Dr. Seuss Museum in Springfield, and the Eric Carle Museum in Amherst. Thrill seakers will love Six Flags New England, young and old will love visiting Yankee Candle, and everyone will love the Magic Wings Butterfly Conservatory in South Deerfield. 

Dining in Western Massachusetts

Western Massachusetts offers a diverse culinary scene, from farm-to-table restaurants to historic inns. Here are some of the many options you’ll find: 

The Red Lion Inn – Stockbridge
A historic landmark, the Red Lion Inn features multiple dining options, including the formal Daniel Webster Restaurant and the more casual Shire Tavern.

Mezze Bistro + Bar –  Williamstown
Enjoy a Mediterranean-inspired menu featuring small plates perfect for sharing.

PUBLIC eat+drink – North Adams
This industrial-chic spot offers a modern take on American comfort food with a focus on local ingredients. The atmosphere is lively, and the cocktail program is impressive.

The Book Mill – Montague 
Lady Killgrew Cafe, the restaurant inside of the Book Mill, offers a unique dining experience with its cozy atmosphere and delicious menu of coffee, sandwiches, and more.

Champney’s Restaurant & Tavern – Historic Deerfield
Located in the historic Deerfield Inn, Champney’s offers a charming blend of classic New England cuisine and modern flair in a cozy, historic setting.

Breweries and Wineries 

Western Massachusetts boasts a thriving craft beer scene with a diverse range of breweries offering everything from classic styles to experimental brews. The region’s rolling hills and fertile land have produced a growing number of wineries, offering a variety of locally produced wines. And, of course, in true New England fashion, the area is brimming with orchards, so the area is littered with cideries as well. Here are some breweries, wineries and cideries you’ll find in the area: 

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Berkshire Brewing Company – South Deerfield 
Offers a wide range of beers, including their popular Purple Haze IPA.

Northampton Brewery – Northampton 
A pioneer in the Massachusetts craft beer scene, known for its consistent quality.

Abandoned Building Brewery – Easthampton 
Focuses on experimental and barrel-aged beers in a unique industrial setting.

Bright Ideas Brewing – North Adams 
Known for its innovative brews and vibrant taproom scene.

Barrington Brewery – Great Barrington 
Offers a family-friendly atmosphere and a wide selection of beers.

Wineries

Black Birch Vineyard – Hatfield 
Offers a variety of wines made with grapes grown in the Connecticut River Valley.

Mineral Hills Winery – Florence 
Produces award-winning wines with a focus on sustainability.

WineHaus – Granby 
Offers a diverse selection of reds, whites and roses. 

Balderdash Cellars – Richmond 
Known for its boutique wines made from grapes grown in the Berkshires.

Hilltop Orchards & Furnace Brook Winery – Richmond 
Offers a wide variety of wines and ciders made from apples grown on the orchard.

Les Trois Emme Vineyard & Winery – New Marlborough 
Produces handcrafted wines with a focus on French varietals.

Cideries

Carr’s Ciderhouse – Hadley 
A classic cider house offering traditional and modern ciders.

Headwater Cider – Hawley
Produces handcrafted ciders using locally grown apples.

Outlook Farm – Westhampton
Their cider, slow-fermented with a touch of honey, spice, or hops, offers a unique and refreshing taste experience. While primarily focused on cider, Outlook Farm also produces a small selection of wines, showcasing the versatility of their orchard’s bounty.

Where to Stay in Western Massachusetts

Blantyre – Lenox

Indulge in luxury at Blantyre, a historic estate offering world-class accommodations, including elegant suites and spacious cottages. Experience impeccable service and enjoy the estate’s extensive amenities.

The Williams Inn – North Adams/Williamstown

The Williams Inn provides a stylish and comfortable stay near MASS MoCA and Williams College. Choose from a selection of standard rooms and suites, designed with modern travelers in mind.

The Inn at Crumpin-Fox – Bernardston

Nestled in the heart of the Massachusetts countryside, The Inn at Crumpin-Fox offers a serene escape. With comfortable rooms featuring modern amenities like refrigerators and televisions, guests can unwind after a day on the golf course or exploring the surrounding area.

Hotel Northampton – Northampton

Experience the heart of downtown Northampton at Hotel Northampton. This historic landmark offers a range of accommodations, from standard rooms to potentially business-oriented options, ensuring a comfortable stay.

MGM Springfield – Springfield

Immerse yourself in the excitement of a casino resort at MGM Springfield. Choose from a variety of guest rooms and suites, featuring modern amenities and stunning city views.

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