One of the most popular towns in the Berkshires is charming Lenox, Massachusetts. You can easily spend a few relaxing days exploring the area’s natural beauty, cultural offerings, and delicious cuisine. During the late spring and summer months, the area is buzzing with visitors and fun things to do. Autumn is a special time in the Berkshires when leaf peepers enjoy a quintessential fall foliage road trip. Winter is cold but holds its own when covered in snow.
Lenox is the perfect destination to immerse yourself in quaint New England charm.
Some information in this piece was obtained during a sponsored press trip, but all recommendations are my own.
1. Boston Symphony Orchestra
The Boston Symphony Orchestra (BSO) brings summertime music to the Berkshires at Tanglewood. The music of the BSO, the Boston Pops (originally the Promenade Concerts and later known as the Popular Concerts), and other popular musicians take the stage for a night of spectacular music in western Massachusetts.
Guests are allowed to bring blankets, lawn chairs, and a picnic dinner to enjoy under the stars when they purchase Lawn tickets. If you are in the Shed or other concert hall, outside food is not allowed for the music shows.
Pro Tip: In July and August, you can experience Saturday Morning Rehearsals for a fraction of the evening ticket prices. Watch as the BSO team shapes and molds the upcoming performance while enjoying scores from the show.
2. Pleasant Valley Wildlife Sanctuary
The Mass Audubon Pleasant Valley Wildlife Sanctuary encompasses over 1,000 acres along the slopes of Lenox Mountain and surrounding area. The area covers lush forests, pretty meadows, and marshy wetlands perfect for bird watching, searching for beaver lodges, and observing local wildlife. The whole family will enjoy the beautiful trails and green spaces.
AllTrails ranks several trails in Pleasant Valley Sanctuary. The hard, 2.6-mile loop — Overbrook Trail and Trail of the Ledges — rewards hikers with a beautiful overlook. A more moderate trail is the 2.5-mile, out-and-back Bluebird Trail and Overbrook Trail, also offering spectacular Berkshire views.
Pro Tip: There is a nominal per-person entry fee for the valley sanctuary.
3. Canyon Ranch
Spa aficionados around the world love Canyon Ranch. With five locations — Lenox, Tucson, Las Vegas, Austin (coming soon), and Woodside, California — you can be pampered across the country.
Its all-inclusive, resort-style spa offers guests both traditional and unique spa experiences along with health and wellness counseling, outdoor activities, and sumptuous cuisine. You can choose a pre-set pathway or sculpt your own spa adventure.
I spent a girls’ getaway at Canyon Ranch and it was one of our best group travel adventures. Three nights away with your besties filled with laughs, exercise, and health and wellness treatments are the perfect ingredients for self-love and good health.
4. Ventfort Hall Mansion And Gilded Age Museum
A 19th-century Gilded Age “cottage,” Ventfort Hall Mansion and Gilded Age Museum represents Lenox’s popular summer resort community of bygone days. The mansion, museum, and grounds offer guests tours, exhibits, and performances throughout the year.
5. Berkshire Scenic Railway Museum
The seasonal Berkshire Scenic Railway Museum is a fun spot for train enthusiasts. Docent-led tours will guide you through the history of local trains. Enjoy a short ride on the Lenox Jitney in restored vintage railroad equipment. You can even book a spot in the locomotive cab and play at being a train engineer.
Pro Tip: Hop aboard the Hoosac Valley Train, departing from the nearby Adams Visitors Center, for an hour-long ride through the beautiful Berkshire landscape.
6. Shopping
Unique specialty shops and galleries in and around Lenox will capture your imagination and tease you into adding stunning new pieces to your home.
An American Craftsman Galleries brings together works from fine artisanal crafts like glass, wood, and other specialty items. A must-stop for any shopper, the American Craftsman Galleries is filled with unique one-of-a-kind items.
The Sohn Fine Art gallery showcases a selection of beautiful and thought-provoking art. The Art and Chocolate gallery offers a little sweet and pretty artwork; it’s a charming shop. Wander around the Annie Selke homegoods shop and explore the bright and colorful décor ideas. Shopping in Lenox is a leisurely pastime where you can discover all the things you didn’t know you really needed.
7. Kripalu Center For Yoga And Health
Another Berkshire health and wellness center is the Kripalu Center for Yoga and Health in nearby Stockbridge. Whether you are seeking yoga for health, toning, or spiritual practice, you will find a class at Kripalu. The peacefulness of the forests surrounding Kripalu is ideal for meditation and self-reflection.
The stunningly picturesque landscape is ideal simply for breathing in the fresh, restorative mountain air.
8. Norman Rockwell Museum
As you wander through the galleries at the Norman Rockwell Museum, the 323 Saturday Evening Post covers will transport you back to another era. Pondering a Rockwell painting reveals more than a simple illustration. Subtle nuances reflecting American values are strategically placed, enhancing the overall topic. Beginning in 1916 and continuing for over 40 years, Rockwell painted tableaus depicting current events and small-town snapshots. Viewing his collective works is a walk through the life and times of rural America.
In addition to exploring the galleries at the Norman Rockwell Museum, you can schedule several interesting tours. A 40-minute-long Rockwell’s Life & Art tour takes you on a journey led by his storytelling and exceptional art. Additionally, enjoy a 20-minute guided tour of Rockwell’s studio and immerse yourself in his inspirational setting.
9. Hancock Shaker Village
In nearby Pittsfield is the Hancock Shaker Village. A lovely pastoral setting radiates from an 1826 centerpiece roundstone dairy barn. The Shaker village encompassed over 3,000 acres in the 1830s, tended by more than 300 Believers. Named “The City of Peace,” the utopian community was a once-prosperous haven for hard-working and peace-loving worshipers.
Today, the Hancock Shaker Village continues its farming traditions and is still operating. Education about Shaker history is an important piece of their mission, bringing life on the farm to their guests. From practicing goat yoga to the Shaker Supper series, there is always something fun, educational, and interesting happening at the Hancock Shaker Village.
Where To Dine
When it comes time to dine, there are terrific options in and around Lenox. Alta Restaurant and Wine Bar offers Mediterranean-inspired, fine-dining cuisine; reservations are recommended. Gateways Dine & Drink is the perfect spot for a quiet dinner date or a sumptuous Sunday brunch. Chic, casual, and delicious, Pizzeria Boema brings the classic Italian pizza tradition to the Berkshires. Breakfast served up straight or with a modern culinary twist, Haven Cafe & Bakery is the place to be for a morning coffee and delightful nosh. Wine time at Balderdash Cellars in nearby Richmond is a picturesque spot to sample a flight of wines, enjoy the Berkshire scenery, and relax with live folk music.
When it is time for dessert, Chocolate Springs Café offers up stunning hand-made chocolates that satisfy an end-of-day, sweet-treat craving.
Where To Stay
In the heart of downtown Lenox is the charming Gateways Inn. The 1912 Gilded Age mansion has been transformed into a beautiful inn. Keeping the historic décor and adding modern amenities, Gateways Inn is a charming blend of old and new. Originally a vacation home for Harley Proctor, of Procter & Gamble fame, the long white mansion’s exterior was built to resemble P&Gs iconic Ivory Soap Bar.
The getaway to Lenox is the perfect jumping-off spot for your Berkshire visit. The area’s beautiful landscapes beckon visitors back year after year. When you want to get away from it all, enjoy an outdoor concert, hike a few miles to discover beautiful overlooks, and explore a rich cultural heritage. Lenox needs to be on your getaway bucket list.
