A Vibrant, Uncrowded Fall Getaway Awaits At This Small But Mighty Massachusetts Mountain Town

There's something magical about autumn in Massachusetts. Whether you're getting in the spooky spirit in the witchy town of Salem, or enjoying a crisp coastal retreat on the shores of Cape Cod, there are plenty of towns where you can spend the season sipping pumpkin spice lattes and basking in the fall foliage.

However, if you want to avoid herds of tourists flocking to the more popular fall-friendly destinations, you can take the road less-traveled to Stockbridge. Tucked unassumingly into Berkshire County, the under 5,000 population town is brimming with all the quaint New England charm you could dream of. Packed with historic homes and gardens, art galleries and museums, cozy inns and B&Bs, gorgeous hikes, and a colonial style downtown, its picturesque setting is straight out of a Norman Rockwell painting. If you're planning your next romantic getaway or relaxing East Coast retreat, this Massachusetts mountain town is perfect for a serene autumnal escape.

Windy Hill Farm, Stockbridge is a New England town frozen in time. Home to a plethora of historic sites, you won't want to miss the town's most renowned attraction: the Norman Rockwell Museum. Boasting the world's largest collection of Rockwell's art, the museum includes his famous painting "Main Street Stockbridge at Christmas," which captures the small town charm of the place where he spent the last 25 years of his life. Open Thursday through Tuesday from 10 A.M. to 5 P.M., you can visit the museum for $25, and tour the Norman Rockwell Studio for an additional $10.

Lined with colonial-style storefronts and restaurants, take a stroll down Main Street, and you'll feel like you're stepping into a real-life Rockwell painting. Slip into Once Upon a Table for European-style bistro fare, or The Main Street Cafe for a charming New England breakfast or lunch. Afterwards, you can continue west down Main Street to marvel at the town's historic homesteads. Built during the Gilded Age, you'll see everything from beautiful cottages like the Mission House, to grandiose estates like the Chesterwood, which houses an art museum and sculpture garden.

If you're looking to catch some fall foliage on your trip, check out the nearby Gould Meadows, which has several easily accessible trails that lead to gorgeous views of the Berkshire mountains. The Mary V. Flynn trail is another popular option recommended for hikers of all levels who want a glimpse of Stockbridge's natural beauty during the autumn season. Finally, for more seasonal outdoor activities, take a short five minute drive outside of town and visit Windy Hill Farm for apple picking.

When it comes to lodging, you won't find any generic chain hotels in Stockbridge. Instead, a selection of historic inns and gorgeous B&Bs await, offering a quintessential New England experience. Hosting six U.S. presidents since opening its doors in 1773 , The Red Lion Inn is an iconic locale filled with vintage furnishings and historic charm. Similar to the famous Concord Colonial Inn — one of the oldest inns still operating in America — the interior will transport you back to the days of The Revolutionary War. You'll also find plenty of onsite dining options, including an Olde English style pub, Widow Bingham's Tavern, and an old-fashioned speakeasy, The Lion's Den.

If you're planning an East Coast couples trip, snuggle up in a romantic B&B. Housed in an 1906 Georgian style mansion on a beautiful 6-acre estate, The Inn at Stockbridge offers an elegant stay in a serene setting that's perfect for lovebirds. Closer to the local attractions, The Stockbridge Country Inn is another favorite amidst travelers that boasts spacious, antique-adorned rooms, and a sparkling pool surrounded by lush greenery. Wherever you choose to stay, an autumnal adventure to Stockbridge promises a peaceful retreat in an idyllic setting.