Lenox, Massachusetts

Nestled in the southern portion of the region, Lenox is the town you’ll have the pleasure of calling home when staying with us at Downtown Upstairs. Often referred to as the cultural capital of the Berkshires, Lenox is packed to the brim with all sorts of sites and attractions, ranging from luxurious wellness retreats and spas to relaxed cultural excursions.

Throughout the small town you’ll find countless examples of both historic New England architecture and Gilded Age opulence. In fact, the town has one of the highest concentrations of Gilded Age mansions in the country, including author Edith Wharton’s home, the Mount, and Bellefontaine Mansion, now the world-famous Canyon Ranch spa and health resort.

Downtown Lenox is also not to be missed. Take a stroll down the tree-lined streets and you’ll find yourself in a picturesque American Main Street, complete with cafes, restaurants, art galleries, local artisan shops, and much more.

In case you're more in the mood for some pampering though, Lenox has gained popularity in recent years as a wellness destination. As just mentioned, Canyon Ranch is located right here in town, but you’ll also find the newly opened Miravel Berkshires Resort and Spa and the Kripalu Center for Yoga and Health.

But above all else, Lenox is most famous for being the home of Tanglewood. In addition to being the summer residence of the Boston Symphony Orchestra, Tanglewood is known for hosting countless concerts, festivals, and performances every single summer. In fact, Tanglewood has actually become one of the main reasons that the Berkshire’s regulars come back and visit year after year!

Tickets for these shows tend to sell out fast though, so be sure to plan and book your trip well in advance if one of your favorite artists is set to perform soon!

In addition to Tanglewood and the downtown area, as is the case with most of the Berkshires, you’re never too far from nature in Lenox. To the south, you’ll find Laurel Lake, where visitors can enjoy boating and lake recreation on sandy beaches. Head east to the area around Olivia’s Overlook and you’ll be able to explore some exceptional hiking trails with panoramic views of the region.

Lenox embodies everything that makes the Berkshires so unique, and no trip to the region would be complete without paying a visit. Additionally, in recent years, the town has seen a dramatic growth in its cultural and hospitality offerings, transforming it from what was once a summertime retreat for the New York and Boston elite into a year-round destination that has something for everyone to enjoy!