As snowflakes cover the world in glistening white, we envision sleighbells, crackling fires, and time spent with those we love. Nothing beats the charm of Massachusetts’ small towns, and we’ve handpicked some of the best hidden gems for you to explore this winter.

Groton, MA

Picturesque Groton stands as a testament to the perfect harmony between rich historical heritage and bucolic rural life. Don’t miss a stay at the Groton Inn, a lovely boutique hotel in the center of town that offers fine dining, a welcoming outdoor courtyard complete with fireplace, and pastoral views of Gibbet Hill topped by the ruins of Bancroft Castle, said to be haunted. Groton gives easy access to area hiking trails and ice fishing for the outdoor enthusiast, plus contemporary art at the Fitchburg Art Museum or amazing concerts at the glorious Groton Hill Music Center for arts lovers. 

Sterling, MA

Quaint Sterling epitomizes the charm and character of a classic New England town. Just minutes from the shores of beautiful Wachusett Reservoir, the ski slopes of Wachusett Mountain or the breathtaking panoramic views of Wachusett Meadow Wildlife Sanctuary, Sterling offers much to delight outdoor lovers. Book a sleighride at Cornerstone Ranch, then a room at the romantic Chocksett Inn to experience legendary New England hospitality. Be sure to visit The Icon Museum in nearby Clinton, which boasts North America’s largest collection of Russian, Greek, and Ethiopian icons and Eastern Christian works of art. 

Hudson, MA

Voted one of the most picturesque small towns in Massachusetts, Hudson is eminently walkable. From the Clover Road Brewing Company on one end of town to Medusa Brewing on the other, you can wander through Hudson’s charming shops and boutiques, with stops in between for a little aerial yoga, an escape room, or a cocktail in a real speakeasy (hidden in a cobbler’s shop!). Just outside of downtown is the American Heritage Museum, full of immersive exhibits highlighting their one-of-a-kind collection of antique planes, tanks, and automobiles. Head a little further down the road to The Wayside Inn in Sudbury—the oldest inn in America offers excellent dining in their cozy restaurant warmed by fireplaces, as well as historical exhibits around the property, including at the beautiful Grist Mill. 

Natick, MA

Surrounding the quintessential Town Common lies the Natick Cultural District, rich with working artists’ studios, interesting shops, farm-to-table restaurants (like chef-owned Buttercup), and fascinating history. Plan to take in a show at TCAN or slightly further afield at Hopkinton Center for the Arts, then hunker down for the night at the Warren Conference Center and Inn. Built on a lake with woods for strolling through, this inn is the epitome of an old-world lodge, complete with massive wooden beams and cozy fireplace in the lobby perfect for snuggling in front of with a warm drink after a day spent snow shoeing or hiking in the nearby state parks.

Sturbridge, MA

With miles of hiking and biking trails, recreation areas, and nature sanctuaries, Sturbridge is at its heart a rural community, but it’s also a charming town in Central Massachusetts that serves as a gateway to New England’s past. Old Sturbridge Village, the largest living history museum in the Northeast, is a recreated 1830s town encompassing 200+ acres and 40 buildings. Winter is particularly lovely in the Village, with horse-drawn sleighrides and fascinating craftsmen that you can watch create cabinets, metalworks, and more. Definitely stay at the Publick House Historic Inn, where they greet your arrival with warm pecan rolls from their Bake Shoppe. 

Worcester, MA

Though technically a city, Worcester feels more like the very best New England town—beautiful old buildings, charming hotels, enticing winter activities, and mouthwatering dining. The Worcester Art Museum has a stunning collection of Old Masters, even older frescoes, and medieval armor juxtaposed with contemporary works. The Hanover Theatre offers plays, concerts, and other performances in a beautiful historic auditorium. Go ice skating on the Oval downtown, and do a little shopping at Vaillancourt Folk Art, famous for their chalkware. Reserve a fireplace suite at the elegant Beechwood Hotel, perfect to cozy up to on a cold winter night. 

Visit TheHeartofMA.com/digital-guide for a free guide to help plan your trip