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Writer's pictureRyan Jones

The Ultimate Guide to Visiting Lenox, MA: Top Things to Do in the Berkshires

If you’re planning a trip to the Berkshires, Lenox, MA, should be at the top of your list. Known for its vibrant arts scene, historic landmarks, and stunning natural beauty, Lenox offers a perfect mix of culture and outdoor recreation. Whether you’re visiting to enjoy a concert at Tanglewood or explore the town’s historic estates, this guide will help you discover the top things to do in Lenox, MA.


Tanglewood in Lenox Massachusetts
Courtesy of Tanglewood

1. Tanglewood: Summer Home of the Boston Symphony Orchestra

No visit to Lenox is complete without experiencing Tanglewood, the summer home of the Boston Symphony Orchestra. Set against the stunning backdrop of the Berkshire Hills, Tanglewood hosts world-class concerts ranging from classical music to contemporary performances. Bring a picnic, relax on the lawn, and enjoy the music in this scenic outdoor venue. Popular performances, including John Williams’ Film Night, are not to be missed.


The Mount in Lenox Massachusetts
Courtesy of The Mount

2. The Mount – Edith Wharton’s Home

Step back in time with a visit to The Mount, the historic home of famed author Edith Wharton. This stunning estate, designed by Wharton herself, is a testament to her architectural and literary talents. Visitors can tour the beautifully preserved mansion, explore its formal gardens, and learn about Wharton’s life and works. The Mount also hosts events like book talks, outdoor theater performances, and lectures throughout the year.



3. Shakespeare & Company

For theater enthusiasts, Shakespeare & Company in Lenox offers some of the best productions of Shakespeare and modern plays in the region. The summer season is particularly popular, with performances taking place in both indoor and outdoor venues. This acclaimed theater company is known for its high-quality performances and commitment to bringing the Bard’s works to life. Be sure to check their schedule for workshops, educational talks, and behind-the-scenes tours.


 Pleasant Valley’s varied trails wind through forests, meadows, wetlands, and along the slopes of Lenox Mountain, making this site an excellent location for easy-to-strenuous hiking. Well worth the hike to the top to be rewarded with a gorgeous panoramic view of the valley and mountain ranges beyond.
Pleasant Valley's Trails | Courtesy of Books P. Trip Advisor

4. Pleasant Valley Wildlife Sanctuary

Nature lovers will enjoy the Pleasant Valley Wildlife Sanctuary, a peaceful retreat with over 1,000 acres of forests, meadows, and wetlands. Managed by Mass Audubon, this sanctuary features several hiking trails, including the popular Lenox Mountain trail, which offers breathtaking views of the Berkshires. Visitors can also enjoy birdwatching, nature programs, and scenic walks along Pike’s Pond. It’s a great place to connect with nature during your visit to Lenox.


Berkshire Scenic Railway Museum
Courtesy of Berkshire Scenic Railway Museum

5. Berkshire Scenic Railway Museum

Take a ride back in time at the Berkshire Scenic Railway Museum. This family-friendly attraction offers scenic train rides through the beautiful Berkshire countryside, showcasing the region’s natural beauty and historical significance. The museum also features exhibits on the history of railroads in the Berkshires, making it an educational and fun experience for visitors of all ages.



6. Explore Lenox’s Cultural and Art Scene

The Berkshires are known for their vibrant arts scene, and Lenox is no exception. Art lovers can explore local galleries such as the Frelinghuysen Morris House & Studio, showcasing modernist art, or stop by The Wit Gallery to discover contemporary works by local artists. Throughout the year, Lenox hosts various art events and festivals that celebrate the town’s creative spirit.


7. Historic Downtown Lenox

A stroll through downtown Lenox is a must during your visit. This charming area is filled with boutique shops, art galleries, and inviting cafes. Be sure to visit The Bookstore, a cozy independent bookstore, and enjoy a meal at Alta Restaurant & Wine Bar, a local favorite. The downtown area is also home to historic inns and hotels, making it a great place to stay and explore the town’s unique New England charm.


Ventfort Hall Mansion in Lenox Massachusetts
Ventfort Hall Mansion | Courtesy of Trig Photography

8. Ventfort Hall Mansion and Gilded Age Museum

Discover the grandeur of the Gilded Age at Ventfort Hall Mansion in Lenox. Built in the 1890s, this impressive mansion has been restored to its former glory and now serves as a museum. Visitors can take guided tours of the mansion’s luxurious rooms and learn about the history of the wealthy families who once lived there. Ventfort Hall also hosts special events, including lectures, teas, and seasonal exhibits.


Miraval Berkshires Resort & Spa view of the lake
Courtesy of Miraval Berkshires Resort & Spa

9. Miraval Berkshires Resort & Spa (Formerly Cranwell Resort)

For those seeking relaxation, the luxurious Miraval Berkshires Resort & Spa (formerly known as Cranwell Resort) offers world-class spa treatments and wellness programs. Set on 380 acres, the resort features an 18-hole golf course, indoor and outdoor pools, fitness classes, and yoga. It’s an ideal destination for those looking to unwind while enjoying the beauty of the Berkshires.



10. Outdoor Recreation in Lenox

Lenox is a perfect destination for outdoor enthusiasts. In addition to the hiking trails at Pleasant Valley, visitors can enjoy kayaking and canoeing on nearby Laurel Lake. During the winter, Lenox transforms into a winter wonderland with cross-country skiing and snowshoeing at Canterbury Farm and Notchview, while Bousquet Mountain and Jiminy Peak offer skiing and snowboarding for all levels.



Conclusion: A Perfect Getaway to Lenox, MA

From world-class performances at Tanglewood to historic estates like The Mount, Lenox, MA, offers a perfect blend of culture, history, and outdoor activities. Whether you're a music lover, nature enthusiast, or history buff, Lenox has something to offer everyone. Plan your visit to this charming Berkshires town and experience the best that Upstate Massachusetts has to offer.


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