The Berkshires is a popular region of western Massachusetts known for its natural beauty and cultural attractions. From hiking and skiing in the snow-capped mountains to visiting world-class museums and attending live performances, there is something for everyone in the Berkshires. If you’re planning a trip to this picturesque region, we’ve got you covered with the top 20 things to do during your visit.

1. Visit the Norman Rockwell Museum

The Norman Rockwell Museum is a must-see for art lovers. The museum features over 600 of Rockwell’s iconic paintings and illustrations, including some of his most famous works like “Freedom from Want” and “Freedom from Fear.” The museum also has a number of temporary exhibitions throughout the year, so there’s always something new to see even if you’re a returning guest.

Source: Visit MA

2. Explore the Massachusetts Museum of Contemporary Art (Mass MoCA)

Mass MoCA is one of our favorite contemporary art museums nationwide! The museum features a wide variety of exhibitions and installations, including works by some of the most talented artists of our time. The museum also hosts a number of music and performance events throughout the year, so be sure to check their calendar before you visit.

Source: New York Times

3. Take a hike on Monument Mountain

If you’re looking for a scenic hike with great views, Monument Mountain is the perfect destination. The mountain is home to several hiking trails, including the popular Monument Trail, which takes you to the summit for panoramic views of the surrounding area. The hike is moderate in difficulty and takes about 2 hours, so pack snacks and plenty of water!

4. Visit the Berkshire Botanical Garden

The Berkshire Botanical Garden is a beautiful 15-acre garden that features a wide variety of plants and flowers. The garden is open year-round and is particularly beautiful in the spring and summer when the flowers are in bloom and Instagram-ready. There are also several walking trails on the property, so you can explore the gardens at your own pace (we like to stop and smell the roses, literally).

5. Enjoy a performance at Tanglewood, the summer home of the Boston Symphony Orchestra

Tanglewood is one of the most famous music venues in the country and the summer home of the beloved Boston Symphony Orchestra. The venue hosts a wide variety of musical performances throughout the summer, including classical music, jazz, and popular music. If you’re a music lover, be sure to check out their calendar before you visit. 

6. Visit the Eric Carle Museum of Picture Book Art

The Eric Carle Museum of Picture Book Art is a must-see for families with children. Eric Carle is a widely popular children’s author with beloved books like The Very Hungry Caterpillar. The museum features a wide variety of picture books, as well as interactive exhibits that are designed to inspire creativity in children. The museum is open year-round and is a perfect family-friendly destination for a rainy day.

7. Take a scenic drive on the Mohawk Trail

The Mohawk Trail is a beautiful scenic drive that takes you through the heart of the Berkshires. The road is lined with stunning views of the mountains and valleys, and there are several lookout points along the way where you can stop and take in the scenery (and take plenty of photos for your social feeds). The drive takes about 2 hours without stops, so pack road trip snacks for the journey!

Source: New York Times

8. Visit the Ventfort Hall Mansion and Gilded Age Museum

The Ventfort Hall Mansion is a beautiful Gilded Age mansion that is open for tours. The mansion is a great example of the opulent homes that were built by the wealthy during the late 19th century. The mansion is also home to the Gilded Age Museum, which features a number of artifacts and exhibits about the history of the period, perfect for the history buff in your life.

9. Explore the natural beauty of Bash Bish Falls

Bash Bish Falls is the highest waterfall in the state of Massachusetts and one of the most beautiful natural attractions in the Berkshires. The falls are located in a state park, and there are several hiking trails to get there, ranging from moderate to difficult. Bonus – the trails are pet-friendly (dogs must be on leash) so you can bring your furry friends along!

Source: Inspired Lifestyle

10. Visit the Berkshire Athenaeum

The Berkshire Athenaeum is another great place to learn about the history of the area, as a public library based off of what was previously a private athenaeum. The library has an expansive collection of historical documents and artifacts, including photographs, maps, and newspapers. They also have a unique collection of local authors and works of literature.

Source: Library Postcards

11. Take a relaxing soak in the natural hot springs at the Cranwell Spa & Golf Resort

The Cranwell Spa & Golf Resort is a great place to relax and unwind. The spa features a variety of services, including massages, body treatments, and facials—a perfect way to get some peace on vacay. They also have a natural hot spring pool that is open year-round, so you can soak and relax in the warm water.

12. Attend a performance at the Williamstown Theatre Festival

The Williamstown Theatre Festival is a summer theater festival that features a variety of plays, musicals, and other performances. The festival is held at several venues in the area and is a great way to experience live theater in a beautiful setting.

13. Visit the Berkshire Hills Eisenberg Camp

The Berkshire Hills Eisenberg Camp is a Jewish summer camp that is open to the public. The camp offers a variety of activities, including swimming, hiking, and arts and crafts. They also have a number of special events throughout the year, so be sure to check their calendar before you visit.

14. Take a guided tour of the historic homes in Stockbridge

Stockbridge is a charming town that is home to a number of historic homes. Many of these homes are open for tours, and they offer a glimpse into the lives of wealthy families who lived in the area during the 19th century.

15. Visit the Lenox Library Association

The Lenox Library Association is an interesting place to learn about the history of the area as well. The library has a wide collection of historical documents and artifacts, including photographs, maps, and newspapers. They also have a unique collection of local authors and works of literature.

Source: Wikipedia

16. Take a trip to the Hancock Shaker Village

The Hancock Shaker Village is a living history museum that is dedicated to preserving the history of the Shakers. The village features a number of historic buildings, including a church, a school, and a barn. In addition to the museum, there’s also a working farm on-site that uses traditional Shaker farming practices. They offer tours, internships, volunteer opportunities, and seeds in the retail shop for you to take home and grow yourself! Keep in mind that the museum is closed during winter months, so make sure to check its website and calendar for open hours. 

Source: Trip Advisor

17. Visit Bartholomew’s Cobble nature reserve

Bartholomew’s Cobble is a nature reserve that is home to a wide variety of plants and animals. The reserve is a great place to go hiking, bird-watching, or just enjoy the scenery. 

18. Enjoy a round of golf at one of the area’s many golf courses

The Berkshires are home to a number of golf courses, including the Cranwell Resort, Spa & Golf Club, and the Taconic Golf Club. These courses offer challenging and beautiful golf experiences and are great for golfers of all skill levels.

19. Check out local vacation rentals

The Berkshires are a popular vacation destination, and there are many vacation rentals available throughout the area. From cozy cabins to large family homes, you can find a rental that suits your needs and budget for your crew. Be sure to check out AvantStay’s vacation rental listings before you plan your trip, to find the perfect place to stay for your group.

In conclusion, the Berkshires is a beautiful area that offers a wide variety of activities and attractions. Whether you’re interested in art, music, history, or the outdoors, there is something for everyone in your group!

Source: AvantStay

Published by Danielle Vito

As Senior Social Media Manager, Danielle manages AvantStay's social media platforms and writes content for the Atlas blog. Previously, Danielle was the Social Media Producer at The Points Guy where she ran TPG's Instagram and wrote articles on the most social media-worthy destinations, and tips on hacking your travels by using credit cards.

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