Islands    •   10 min read

Massachusetts' 'Gateway To The Berkshires' Is A Postcard Town With Classic New England Charms And Cozy Inns

WHAT'S THE STORY?

downtown district of Lee, Massachusetts

A vacation to New England is bound to be memorable. From quaint farms in Connecticut filled with four-season delights to the stretch of scenic coastline in Massachusetts and Rhode Island that boasts amazing fresh-off-the-boat seafood, there's a new adventure waiting in every corner. And tucked along lush foothills is Lee, a charming small town sometimes called "the gateway to the Berkshires" for its proximity to the delights of Berkshire County's idyllic landscape. With a cozy main street with historic

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buildings, elegant townhouses, and a serene public park, Lee is the perfect postcard of an iconic New England community. Thanks to a bustling downtown district bursting with shops, nearby lakes, and hiking trails, the town offers something exciting for all types of travelers.

Founded around the 1760s, the town was named for General Charles Lee, a prominent officer during the Revolutionary War. The town is about two hours west of Boston by car, so you could easily visit on a quick day trip escape from the busy city. Better yet, make it a weekend getaway and enjoy a cozy time relaxing in one of Lee's many quaint bed and breakfasts or charming country inns. Visit between June and September for the Farmer's Market, where you can pick up all sorts of local produce and fresh goodies. Plus, a visit in the summer means you'll get to see the flower baskets hanging from the lampposts around town, adding a storybook flair to an already magical town.

Just a short drive away is Basin Pond Trailhead and October Mountain State Forest, where you'll find trails through stunning woodlands, great fishing spots, and picnic areas for the family to enjoy. Also nearby is Laurel Lake, a great place for a refreshing swim in calm waters or to simply relax in one of the Adirondack chairs on the green lakeshore.

Read more: The Best Vacation Destinations Where The US Dollar Goes Furthest

Fun Things To Do In Lee, Massachusetts

The Mount, home of American author Edith Wharton near Lee, Massachusetts

Start off your adventure in Lee with a walk around the historic district. Here you'll find the First Congregational Church, a magnificent Romanesque edifice with a majestic steeple towering 150 feet over the square. Next, enjoy a stroll around Church Park, its shady trees and water fountains fringed by stately Victorian-style homes. Anyone who enjoys a good book should definitely stop by the Lee Library, a Carnegie library built from local marble, and history buffs might enjoy the Civil War Memorial Hall, another marble structure where plaques are inscribed with the names of local Union soldiers who lost their lives.

For a little retail therapy, head to downtown Main Street and browse the local boutiques. Finders Keepers is a vast antique store known for rare finds, while Paperdilly stocks all kinds of cute stationery. If you're at Laurel Lake, stop at the Retro Pop Shop to pick up unique collectibles and retro memorabilia, plus a few refreshing scoops from the adjoining ice cream stand.

Lovers of classic literature and refined architecture shouldn't miss The Mount. Found just a 10-minute drive away, this stunning, whitewashed Italianate villa, built around 1902, was the home of celebrated American author Edith Wharton, best known for her Pulitzer Prize-winning novel, "The Age of Innocence." A guided tour explores the opulent bedrooms, salons, and impressive library where Wharton and her husband lived for ten years. The tours sell out fast, but you can also explore The Mount at your own pace. There's a café that serves light refreshments if you get hungry, and a bookstore where you can purchase souvenirs. Stroll through the stunning formal gardens surrounding the house before heading back into downtown Lee to grab a hearty meal at the end of the day.

Places To Eat In Lee, And Cozy Inns For A Memorable Stay

the library inside Edith Wharton's home near Lee, Massachusetts

Whether you're craving fancy French dishes, fresh seafood, or comforting pub favorites and craft brews, Lee has it all. Located conveniently on Main Street is Chez Nous, a French bistro where you can dine outdoors on the porch or indoors amidst a cozy bar setting. The menu offers a range of tasty French classics like boeuf bourguignon, salad lyonnaise, and salmon poached in chardonnay, plus a selection of delicious desserts. Also on Main Street is Alpamayo Restaurant, a cozy eatery serving authentic Peruvian cuisine. Or, if you prefer, you can grab coffee at the Barrington Coffee Roasting Company or sip whiskey and relax at Moe's Tavern.

For a memorable stay in Lee, book a night at the Devonfield Inn, a stunning bed and breakfast ranch set amidst acres of parkland not far from Main Street. Dating to the 1800s, the Devonfield is elegantly furnished with antique pieces and modern amenities, making you feel like a guest in a stately country manor. For a more cozy experience, try the Chambery Inn on Main Street, a former parochial schoolhouse now offering charming guest rooms inspired by French design. A select number of rooms also boast canopy beds and a fireplace. Then, grab a scrumptious breakfast down the street at the Starving Artist Cafe and Creperie, where they have options like French toast, granola parfait, or skinny pancakes dusted with sugar.

To extend your trip with a little added excitement, you can drive an hour north to the town of Savoy, where you'll find the Savoy Mountain State Forest, which hides a scenic trail to a mesmerizing waterfall. Or, perhaps you'll opt to stay a few days longer in Lee and soak up the quaint New England atmosphere. No doubt you will leave feeling refreshed after a visit to this idyllic Berkshires town.

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