How Many Towns Are in the Berkshires?
The Berkshires are made up of 32 towns in total, each with its own charm and character. While some towns are more well-known, others remain hidden gems. Let’s explore a few of the most popular, as well as some lesser-known towns in the Berkshires, and what makes them a must-see.
Lenox
Lenox is perhaps one of the best-known towns in the Berkshires, and for good reason. It’s the ideal place to look for a combination of art, history, and nature, especially in the summer. Lenox is home to the Tanglewood Music Festival, the summer home of the Boston Symphony Orchestra, where music lovers can enjoy outdoor concerts in a beautiful natural setting.
While you’re here, visit Ventfort Hall Mansion and Gilded Age Museum to witness the area’s rich history and stunning architecture from the late 19th century. October Mountain State Forest is also just a short drive away, offering hiking trails with sweeping views, while nearby Stockbridge Bowl provides opportunities for swimming and boating.
Stay at Hampton Terrace Inn, Canyon Ranch Lenox, or The Yankee while you’re here for a superior lodging experience.
Great Barrington
Great Barrington is the quintessential Berkshire town, offering you a little bit of everything when it comes to a Berkshires vacation. A hub for arts, outdoor recreation, and food, this town is perfect for those who want to explore the Berkshires’ diverse offerings. The Mahaiwe Performing Arts Center hosts concerts, theater performances, and films, attracting top-tier talent. Venture through the town’s several art galleries and boutiques that offer local crafts and fine art. Great Barrington is also a foodie's paradise, with farm-to-table restaurants, local coffee shops, and a vibrant farmers market offering fresh, locally sourced produce.
Nearby Bash Bish Falls State Park is a fan favorite and just a short drive away. The park features a stunning waterfall and trails for hiking. Great Barrington is close to Lake Mansfield as well, where you can enjoy kayaking, swimming, or a leisurely walk around the lake.
In search of a place to stay? Both The Little Lion and Race Brook Lodge offer a rustic and charming take on country quaintness.
Stockbridge
Stockbridge is a must-visit for history and art lovers. The town is famous for its connections to Norman Rockwell, who lived and worked here for much of his life. The Norman Rockwell Museum is an iconic destination for you to visit, showcasing a large collection of his original works, depicting everyday American life in a nostalgic and heartwarming way. Stockbridge is also a great spot for shopping, with its charming main street offering unique stores, antique shops, and local boutiques. When it comes to dining, you’ll find plenty of cozy restaurants, many featuring locally sourced ingredients. Looking to get outside? Visit Beartown State Forest to hike, picnic, or simply enjoy nature.
Your Berkshires weekend getaway isn’t complete without a place to stay. The Red Lion Inn has been hosting generations of folks upholding family traditions and making memories. Situated in the lovely village setting of Stockbridge, the inn is centrally located to the Berkshires’ arts attractions and outdoor activities.
Cheshire
Time for a hidden gem: Cheshire is a small town that offers a charming and low-key atmosphere, perfect if you’re looking to escape the crowds. Located near Mount Greylock, Cheshire is a great place to enjoy outdoor activities, including hiking and birdwatching. The Ashuwillticook Rail Trail, a scenic biking and walking path, is a highlight, offering stunning views of the Hoosic River and surrounding landscape.
The town’s quaint downtown area offers both local shops, and family-owned eateries where you can enjoy a relaxing meal. Cheshire is an ideal choice if you want to experience the Berkshires' natural beauty without the busyness of larger towns.
Our lodging recommendations in the area: Hotel on North, Hotel Downstreet, The Porches Inn at MASS MoCA, or The Williams Inn.
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