The Best Things to Do in Lenox, MA

The Mount Edith Wharton's Historic Home

Nestled in the Berkshire’s gentle hills, sophisticated Lenox is etched on the map of art lovers. Culture vultures flock to this corner of New England for its packed calendar of performing arts events. Stroll the manicured streets and you’ll be treated to galleries, independently owned shops and fine restaurants.

Keep your eyes open for Gilded Age mansions neatly tucked away on side streets. There’s an emphasis on wellness, with spas and retreats (including Canyon Ranch, Kripalu Center and Cranwell) in abundance, so schedule a nourishing massage between performances. Lenox is the ideal place to invigorate body and spirit.

The Must-Do Experiences

Shakespeare & Company outdoor performance

Music lovers make seasonal pilgrimages to Tanglewood, summer home of the Boston Symphony Orchestra. Classical, jazz and popular music magically blend with the sounds of nature as you listen on the rolling lawn. The grandeur of the acoustics is rivaled by the gourmet spreads that picnickers tote with them, feasting while the concert is being performed. Tanglewood is one mile from town.

If the Bard is more your style, Shakespeare & Company is located in the center of town, surrounded by meadows. While much of the programing is Shakespeare-centric, they’re known for spearheading ambitious new works. The season runs May-March.

Lenox was once known as the inland Newport, thanks to its plentiful number of sumptuous summer “cottages.” Ventfort Hall’s original details and stained-glass windows have garnered Hollywood’s attention (you might remember it from The Cider House Rules). Savvy travelers come for the Tea and Talk lecture series. You’ll listen to a guest speaker and indulge in a Victorian tea so authentic, you expect the cast of Downton Abbey to appear and daintily dollop clotted cream on a scone.

The Mount

Literati won’t want to miss visiting The Mount, author Edith Wharton’s stately self-designed home. The elaborate gardens include an Italian walled garden and formal French flower garden. Delve into the paranormal when you join a twilight ghost tour and enjoy free live music on weekend evenings. Open May 1-October.

The Eats

Brava Tapas Bar in Lenox

Casual Brava has brought tapas to town. Gourmet pizzas, small plates, creative salads and bite-sized nibbles pair perfectly with the top-notch wine list, with dozens of delectable by-the-glass offerings. Enjoy an intimate table with your honey or grab a seat at the welcoming bar.

Even Willy Wonka would be impressed by the intoxicating creations sold at Chocolate Springs Café. Cakes, sorbets, and confections are made from the highest quality cocoa beans. There’s nothing but chocolate on the menu, but no one’s complaining.

The Insider Tip

Kennedy Park Trails in Lenox

Don’t let the smorgasbord of cultural opportunities deter you from exploring the gorgeous natural surroundings. Kennedy Park is right off Main Street Lenox. This hardwood forest offers 15 miles of trails, ideal for hiking and groomed for cross-country skiing in winter.

The Digs

Garden Gables Inn B&B Room

Hampton Terrace is one of the Northeast’s finest bed and breakfast establishments, with a mint location in the heart of the village. If you’re looking for a roaring fireplace, Jacuzzi tub, gourmet breakfast with a Southern-twist, complimentary cognac bar and convivial on-site innkeepers, you can’t do better. Seasonal heated outdoor pool. Rooms from $229.

Garden Gables Inn is situated on five leafy acres in Lenox. Fifteen cozy rooms, heated outdoor pool and nightly sherry add an elegant note. Rooms from $220.

The Directions to Lenox from NYC

Ride the Peter Pan bus lines from Port Authority to Lenox in three hours.

For more information on visiting Lenox, go to and head to

Photos: Respective properties, Massachusetts Office of Travel & Tourism, mwms1916 for Kennedy Park