The Heart of the Berkshires - LEE - Northeast Traveler Magazine

When I stroll through the heart of Lee, Massachusetts in October, the crisp autumn air filled my lungs, and the vibrant hues of fall foliage painted the town in a breathtaking palette of reds, oranges, and yellows. The classic New England square, with its historic buildings and quaint shops, felt like stepping into a postcard.

Leaves crunch underfoot as I wandered past charming boutiques, cozy cafes, and the iconic Joe’s Diner, where the aroma of freshly brewed coffee and homemade pies wafted through the air. Seasonal decorations adorned the storefronts, with pumpkins, gourds, and cornstalks adding to the festive atmosphere.

Walking around downtown Lee, I can’t help but admire the beautifully preserved architecture.

The Congregational Church, with its towering steeple (the tallest wooden steeple in the country), is iconic New England. This church features beautiful trompe l’oeil stenciling inside, making it a significant example of this almost-forgotten craft.

The Lee Library, built from local marble, adds a touch of elegance to the streetscape. Each storefront seems to invite exploration, from antique shops brimming with unique finds to art galleries showcasing local talent. The crisp air carries the faint scent of wood smoke, a reminder of the cozy fireplaces that would soon be lit as the evenings grew cooler.

Lee occupies land that was originally the territory of the Mahican Indians. The first non-native settlement in the area, known as Dodgetown, was established around 1760 by Asahel Dodge, who migrated from Cape Cod. Lee was officially incorporated in 1777, named after Revolutionary War General Charles Lee.

In its early years, Lee was a bustling mill town. The abundant streams and rivers provided the necessary water power for mills that produced textiles and wire. By 1806, papermaking had become the town’s principal industry with the construction of the Willow Mill by Samuel Church in South Lee.

The Columbia Mill, established in 1827, became the first to supply 100% groundwood newsprint to The New York Times.

Lee’s marble industry also flourished in the 19th century. The town’s high-quality marble was used in notable buildings such as a wing of the Capitol in Washington, D.C., and St. Patrick’s Cathedral in New York City. The prosperity of this era is still evident in the town’s architecture, including its town hall, library, and several historic churches and homes.

Today, Lee retains its historical charm while embracing modernity, making it a fascinating destination for history enthusiasts and travelers alike.

Lee’s downtown is a shopper’s delight, with a variety of unique stores and boutiques.

Main Street Books is a beloved independent bookstore offering a cozy atmosphere and a carefully curated selection of books, from bestsellers to local authors. It’s a perfect spot to find a new read or enjoy a quiet moment amidst the hustle and bustle of Main Street. The knowledgeable staff and frequent author events make it a hub for book lovers.

Whether you’re looking for the latest bestseller or a rare find, Main Street Books has something for every reader. The scent of freshly brewed coffee from a nearby cafe mingles with the crisp pages of new books, creating an inviting ambiance.

Paperdilly is another charming shop in downtown Lee, offering a delightful selection of stationery, greeting cards, gifts, and unique paper products. It’s a great place to find a special souvenir or a thoughtful gift for someone back home. The store’s whimsical atmosphere and friendly staff make shopping here a pleasure. The shelves are adorned with colorful paper goods, and the sound of soft music adds to the relaxed shopping experience.

For those looking for fresh, organic, and locally sourced products, Berkshires Green Grocer is the place to go. Located at 42 Park Street, this local grocery store offers a wide selection of gourmet foods and specialty items.

The attached Claire’s Cafe provides a cozy spot to enjoy a meal or a coffee while shopping. The aroma of freshly baked bread and the sight of vibrant, locally grown produce make this a must-visit spot for food enthusiasts.

One of my favorite spots for a meal in downtown Lee is The Starving Artist Creperie and Cafe. This delightful venue combines an art gallery with a cozy cafe, creating a vibrant and creative atmosphere. As you enjoy a freshly made crepe—whether sweet or savory—you can admire the local artwork that adorns the walls.

The cafe also serves fair-trade and organic coffee, making it a perfect place to relax and soak in the artistic ambiance. The friendly staff and the ever-changing art exhibits make each visit a unique experience. The menu changes seasonally, ensuring that there’s always something new and delicious to try. The cafe also offers a variety of other gourmet foods, including panini sandwiches, soups, salads, and baked goods, all made with quality local and organic ingredients.

The warm, inviting interior, with its rustic wooden tables and soft lighting, makes it an ideal spot to escape the autumn chill.

Just next door, the Good Purpose Gallery showcases the works of artists who identify as neurodiverse, as well as local artists and artisans from the Berkshires, adding another layer of artistic charm to your visit.

For more dining options, Lee offers a variety of restaurants to suit every palate. Joe’s Diner is a classic American diner known for its friendly service and hearty meals.

If you’re in the mood for seafood, Salmon Run Fish House is a must-visit, offering delicious seafood dishes in a charming setting. For a taste of international cuisine, Mint Indian Lakeside Dining provides a delightful array of Indian dishes with a beautiful lakeside view.

Arizona Pizza Company is another great option, known for its wood- fired pizzas, burgers, and a variety of other dishes. The full bar offers a selection of craft beers, wines, and cocktails, making it a perfect spot for a casual meal.

Another local favorite is 51 Park Restaurant & Tavern, which offers a diverse menu featuring everything from truffle fries to bacon jam burgers. For a more intimate dining experience, Chez Nous Bistro serves exquisite French cuisine in a cozy, welcoming environment.

The Morgan House Inn & Restaurant is a beloved establishment right on Main Street. This historic inn has been serving guests since 1853. Known for its romantic ambiance and proximity to local attractions, the Morgan House offers comfortable accommodations and a delightful dining experience.

The restaurant is well-regarded for its American cuisine, featuring dishes like pot roast, turkey, and a variety of steaks. It’s a perfect spot to enjoy a meal after a day of exploring the town.

The inn’s charming rooms, each uniquely decorated, provide a cozy retreat for travelers. Guests can enjoy modern amenities while soaking in the historic charm of the building. The creaking wooden floors and antique furnishings add to the nostalgic feel, making it a memorable place to stay.

For those looking for other lodging options, Lee has a variety of accommodations to suit different preferences and budgets. The Black Swan Lee – Lenox, Ascend Hotel Collection is a popular choice, offering beautiful lake views, comfortable rooms, and an on-site restaurant. Another charming option is the Chambery Inn, a historic bed and breakfast with French-inspired decor and lush gardens.

During my most recent stay in Lee, we had the pleasure of making the Holiday Inn Club Vacations Oak n’ Spruce Resort in South Lee our hoe base. This timeshare resort offered a perfect blend of comfort and

convenience, with spacious villas, a fully equipped kitchen, and a cozy living area. After a day of exploring, we enjoyed unwinding at the resort’s indoor pool and catching a movie at the on-site theater.

If you prefer a more personalized experience, consider booking an Airbnb. Lee has numerous highly-rated vacation rentals, from cozy cottages to spacious homes.

October in Lee is a time of celebration and community.

The Lee Farmers Market is a must-visit, offering fresh produce, artisanal goods, and a chance to mingle with friendly locals. For those seeking a bit of adventure, appropriately-named October Mountain State Forest just north of Lee provides ample opportunities for hiking, biking, and leaf-peeping. The trails here offer stunning vistas of the Berkshires, making it a perfect spot for nature enthusiasts.

A short drive away, the Norman Rockwell Museum in Stockbridge offers a glimpse into the world of one of America’s most beloved artists. The museum’s exhibitions, including “What, Me Worry? The Art and Humor of MAD Magazine,” are sure to delight visitors of all ages.

October is brimming with events that capture the spirit of the season. The Lenox Apple Squeeze is a delightful festival celebrating all things apple, from cider to pies.

For a touch of the macabre, the First Annual Masquerade Macabre at Ventfort Hall Mansion, also in Lenox, promises an evening of mystery and intrigue. And don’t miss the Ghost Tour with Robert Oakes, where you’ll hear spine-chilling tales of the Berkshires’ haunted history.

Another highlight is the Lee Art in the Park festival, which features the creative works of over 35 juried artists, including photography, drawing, ceramics, jewelry, painting, mixed media, printmaking, fiber, metal sculpture, and glass. The festival also includes an international food court and live music, making it a vibrant cultural event.

Just a short drive southwest of Lee, the Goose Pond Wildlife Management Area offers a tranquil escape into nature. This 94-acre wilderness park is a haven for outdoor enthusiasts, with its network of hiking trails that meander through dense forests and along the serene shores of Goose Pond.

In my hikes along these trails, I’ve been treated to breathtaking views of the Berkshires, making it a perfect spot for leaf-peeping during the fall season. The area is rich in wildlife, so keep an eye out for deer, beavers, and a variety of bird species.

After a day of exploring nature, you might want to check out some local arts venues. The Spectrum Playhouse, housed in the former St. George’s Church, is a multi-purpose performance space hosting a variety of events, including theatre productions, concerts, and community gatherings. Its mission includes developing the performing and visual arts talents of young adults with learning differences, making it a unique and inclusive cultural hub.

Additionally, Tanglewood, located nearby in Lenox, is one of the country’s premier summer music festivals and the summer home of the Boston Symphony Orchestra since 1937. Even in the off-season, the grounds are open for visitors to explore, offering a serene setting for a leisurely autumn stroll.

Lee, Massachusetts, in October is a destination that promises unforgettable experiences and stunning natural beauty. Whether you’re wandering the historic downtown, exploring the scenic trails, or immersing yourself in local events, there’s something for everyone. So pack your bags, grab your camera, and come see for yourself why Lee is a leaf-peeping paradise. Your autumn adventure awaits!

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