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
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.
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
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
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
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 www.berkshires.org and head to www.Lenox.org.
Photos: Respective properties, Massachusetts Office of Travel & Tourism, mwms1916 for Kennedy Park
Allison is a native New Yorker, who has lived in Rome, Tuscany, Melbourne, Toronto and Los Angeles. She frequently contributes travel pieces to Family Travel Forum, using her own children as guinea pigs as they travel the globe. She is fluent in Italian and Spanish and laughably adequate in French. Her background as an Early Childhood Educator gives her an added understanding of what it takes to travel with kids in tow. She firmly believes that the most important part of education takes place outside of the classroom, on the road, around the world. She never misses a chance to sample local delicacies, as her love for travel goes hand-in-hand with her love for food and wine. Follow Allison at @gourmetrav.
Sarah Knapp is a Brooklyn based entrepreneur whose love for the outdoors and community building led her to the October 2013 creation of OutdoorFest. She has a BA in History, is a Wilderness First Responder and a NY state hiking, camp and boating guide. Her proudest achievement to date is reading the Aeneid in Latin. 
Allison was one of our first top writers and Chief Editor but is no longer working with offMetro. Allison is a native New Yorker, who has lived in Rome, Tuscany, Melbourne, Toronto and Los Angeles. She frequently contributed travel pieces to Family Travel Forum, using her own children as guinea pigs as they travel the globe. She never missed a chance to sample local delicacies, as her love for travel goes hand-in-hand with her love for food and wine. 
Josh Laskin is a freelance travel writer and photographer based in the White Mountains of New Hampshire. When he is not at work or on the road, you can find him in the mountains snowboarding, climbing, hiking, fly fishing, mountain biking, and eating bagel bites.
Annie is a travel writer, environmentalist, and surfer based in Venice, CA. She heads up our West Coast team, keeps our grammatical errors in check, and makes sure our California writers always have a plan for their next adventure. Follow Annie’s travels @annelisemcb.
Carly Pifer is a freelance writer who has been known to follow whims inspired by romantic movie scenes or colorful street style shots to India, Japan, Tunisia and Argentina. After stints living in Seoul, Boston, Paris and Los Angeles, writing and searching for something intangible, she landed somewhat steadily in Brooklyn and has begun to find inspiration in her more immediate surroundings. 
Kate E. O’Hara is a New York based freelance writer and photographer who loves all things food—especially the people who make it and market it. Her writing aims to capture the essence of the food experience; the stories that go well beyond a plate of ingredients. In addition to her love of food, Kate is also known to have a hankering for red wine and craft beer. You can also find Kate on Instagram