Our Favorite Things To Do In Western Massachusetts
This season, discover a new destination to add to your bucket list that you’ll want to keep revisiting time and time again. Western Massachusetts has something for everyone - from skiing + après-ski, to culture + cocktails, to literature, wellness, and everything in between!
Let Pack Up + Go plan your dream getaway to Western Mass with a You Pick Trip, or snag a Picks Destination Guide for the best things to see, do, and eat in the region!
Here are some of our favorite things to do in Western Mass!
Ski + Après Ski:
Western Mass is a leading destination for ski + après ski, sporting multiple resorts to fit the needs of families, couples, large groups, and solo travelers.
Berkshire East Mountain Resort: Berkshire East Mountain Resort is perfect for ski and après-ski lovers, showcasing diverse trails, night skiing, and eco-friendly operations powered by renewable energy. After a day on the slopes, relax at The Crazy Horse Bar & Grill with delicious food, craft beers, and unique decor and architecture. With its welcoming atmosphere, year-round outdoor adventures, and cozy vibes, Berkshire East is perfect for both thrilling skiing and cozy après-ski relaxation.
Jiminy Peak: Experience Jiminy's fantastic skiing experience with various beautiful trails and even a thrilling Alpine Mountain Coaster. If you work up an appetite, get some grub at John Harvard’s Restaurant & Brewery with hearty meals, hand-made cocktails, and a warm ambiance, perfect for après-ski lounging. Jiminy Peak combines nature exploration with quaint mountain charm, making it a great destination for winter enthusiasts.
Bousquet Mountain: You can find Bousquet Mountain and spend a day skiing, tubing, or snowboarding while enjoying the breathtaking natural scenery of the area. After a day of play, hit up Drifters for chef specials, comfy seating, and even live music. Their ski + stay packages make it easy to plan the perfect vacation of exhilaration and tranquility.
Culture + Cocktails:
From world-class museums to nationally-renowned cocktail bars, no trip to Western Mass would be complete without a stop at these local gems.
Mass MOCA: The Massachusetts Museum of Contemporary Art is a must-visit for its cutting-edge exhibitions, featuring large-scale contemporary art installations that can’t be found anywhere else. Housed in a sprawling, repurposed factory complex, the museum offers a unique blend of industrial architecture and modern creativity. It’s also a vibrant cultural hub, hosting live music, performances, and events that make every visit dynamic and engaging.
Norman Rockwell Museum: The Norman Rockwell Museum offers visitors an extensive collection of the artist's iconic illustrations, including his celebrated Saturday Evening Post covers. Guests can explore rotating exhibitions, an immersive studio tour, and interactive programs that delve into Rockwell’s creative process and influence on American culture. The museum is set in the scenic Berkshires, providing a picturesque backdrop for an enriching artistic experience.
Naismith Basketball Hall of Fame: The Naismith Basketball Hall of Fame celebrates the history and legends of basketball, from its invention to the modern game. Visitors can explore interactive exhibits, memorabilia from iconic players and teams, and an iconic dome-shaped court where they can shoot hoops. As the birthplace of basketball, Springfield provides a fitting home for this museum, making it a must-see for basketball fans.
Clark Art Institute: The Clark Art Institute combines a world-class collection of European and American art by masters such as Renoir, Degas, and Turner. Visitors can also enjoy the institute’s elegant architecture and outdoor walking trails!
Yankee Candle Village: Pay a visit to the charming + cozy Yankee Candle Village. In addition to visiting the flagship store of the iconic brand, visitors can also make their own candles! It’s the perfect way to get a relaxing keepsake to take home as a souvenir.
The Tunnel Bar: The Tunnel Bar doesn’t take reservations, but it should absolutely be on your Western Mass bucket list! Located within the historic Union Station, the tunnel bar has been listed as one of the most unique bars in America. You don’t want to miss it!
Dewey’s Lounge: If you’re looking for live music and a world-class cocktail, look no further than Dewey’s! Located in the heart of Springfield, Dewey’s is a must-visit for your trip to Western Mass. We love their cocktail menu and the local musicians who perform many nights a week.
Hilltop Orchards: Visit Hilltop Orchards and discover this stunning working farm producing delectable wines and craft ciders from 27 different varieties of apples. Enjoy tastings, tours, and hikes on the property, and snag some of their ciders to take home with you!
Notch 8 Grille: This local favorite is known for their delicious steak and seafood options, as well as their incredible bar program. Their drink menu has something for everyone, from delicious wines, to cocktails, to mocktails!
Literature Buffs:
Did you know that Western Mass was home to some of the country’s most famous authors? On your visit, you can visit their homes and learn more about them!
Mark Twain House: Literature buffs will love visiting the Mark Twain House, where the ‘father of American literature’ lived and wrote several of his most famous works, including the Adventures of Huckleberry Fin and The Adventures of Tom Sawyer. Today, visitors can tour the beautiful house, the beautiful grounds, and enjoy food at the on-site cafe.
The Amazing World of Dr. Seuss Museum: All literature buffs have one thing in common: they all read Dr. Seuss as a child. Dr. Seuss was a Western Mass native, and visitors to the museum can now learn more about the world-famous author, see never-published pieces of art, and engage with his art and creations in real life!
The Eric Carle Museum of Picture Book Art: Founded in 2002 by Eric and Barbara Carle, this museum is dedicated to preserving and showcasing picture book art. They created a place for families and communities to come together and celebrate the joy and artistry of literature in order to encourage everyone to read and appreciate the beauty around them.
The Mount, Edith Wharton’s Home: This National Historic Landmark was Edith Wharton’s home, where she resided when she wrote some of her most famous works. Today, visitors can enjoy the beautiful grounds, take a tour (including ghost tours!), or enjoy a bite to eat in the cafe. The Mount is open from May through October.
Wellness:
You’re guaranteed to leave Western Mass feeling rejuvenated. Paying a visit to these recommendations will ensure you have a wellness-focused experience!
Miraval Berkshires Resort and Spa: The renowned resort’s Western Mass location is the perfect place to relax and rejuvenate! Even if you’re not staying on-site, if you’re looking for a spa day, you can purchase a day pass to their incredible spa.
Canyon Ranch: A visit to Canyon Ranch will leave you feeling completely refreshed. The all-inclusive spa resort is known for their incredible food, wellness activities, and spa treatments. Staying at Canyon Ranch is an experience you won’t want to miss!
Mohawk Trail: Relax outdoors on this scenic road! It’s an excellent spot for hiking, offering a mix of stunning trails that cater to various skill levels. The area boasts gorgeous views of the Berkshires, lush forests, waterfalls, and opportunities to spot wildlife along the way. Popular hiking destinations along the trail include Mount Greylock, the highest peak in Massachusetts, and the Hairpin Turn overlook, which provides breathtaking panoramic vistas.
Family Activities:
Traveling with families is a breeze in Western Mass! There are so many great museums and sightseeing opportunities that the whole family will love. Here are a few of our favorites!
Magic Wings Butterfly Conservatory + Gardens: Visitors of all ages will love this attraction. The 18,000 sq. ft. facility is filled with butterflies, moths, and tropical vegetation. Even if the weather is chilly outside, the space will feel like a tropical wonderland, complete with over 3,000 butterflies of all colors, shapes, and sizes. You won’t want to miss it!
Springfield Museums: With a host of different collections, varying in focuses and histories, Springfield Museums are home to renowned artists, animals, a Dr. Suess sculpture garden, and so much more. The five museums are D’Amour Museum of Fine Arts, George Walter Vincent Smith Art Museum, Amazing World of Dr. Seuss Museum, Science Museum, and Wood Museum of Springfield History, leaving no subject untouched, creating a vast world of unforgettable experiences and lessons for the whole family to learn together.