The Best Small Towns in New England to Relax in 2024

Stretching along the northeastern corner of the United States, the region known as New England is dotted with quaint coastal towns and charming historic villages. Famous for their striking fall colors, maritime playgrounds, and Old World architecture, the delights of these small-town gems offer endless adventures. From the enchanting cobblestone streets of Salem, Massachusetts, to the picturesque waterfront of Portsmouth, New Hampshire, there are plenty of enchanting locations fit for a relaxing East Coast getaway.

Salem, Massachusetts

Just north of Boston, the enchanting town of Salem is filled with spooky tales. Home to the infamous Salem Witch Trials of 1692, it’s a popular Halloween destination that draws visitors from all over the world. Local museums like The Witch History Museum and historic farms like The Witch House offer deep dives into the town’s spooky history. After learning about the origins of the witch hysteria of the 1600s, visitors can pay their respects to the victims at the Salem Witch Trials Memorial. For an enchanting afternoon stroll, the cobblestone streets of Salem Witch Village are lined with enchanting shops filled with mystical trinkets and treasures. Fans of Hocus Pocus you can visit famous film locations such as Old Town Hall, The Ropes Mansion and The Old Burial Hill Cemetery. Wrapped in colonial charm and magical allure, Salem is sure to enchant you.

Sleeping Cave, New York

Less than an hour by train from New York City, on the edge of New England, lies Sleepy Hollow. Named after Washington Irving’s classic horror story, “The Legend of Sleepy Hollow,” the legendary village is a favorite in the fall, especially around All Hallow’s Eve. While you won’t see the Headless Horseman galloping through town, Sleepy Hollow Cemetery is home to a statue of the grisly horseman and is the final resting place of Irving himself. In October, Halloween enthusiasts can enjoy spooky events like the SUP Witches Festival and the Haunted Hayride. Visitors can also wander through The Old Dutch Church, which dates back to the 1600s, and the Kykuit Rockefeller Estate, a majestic mansion surrounded by beautiful gardens. For a quiet, fairytale escape from the Big Apple, Sleepy Hollow is the perfect destination.

Stowe, Vermont

Nestled at the base of Vermont’s tallest mountain, Mount Mansfield, lies beautiful Stowe. A popular destination for skiers and snowboarders, the mountain resort town offers picturesque views, historic buildings, and a vibrant arts and culture scene. The natural landscape is especially breathtaking in the fall, when the foliage bursts with autumn colors, and in the colder months when snow transforms the town into a winter wonderland. Stowe is full of Old World charm and boasts three classic covered bridges, including the eerie Emily’s Bridge, said to be haunted by the lovelorn ghost of Emily. Boasting romantic mountain getaways and historic New England retreats, Stowe has it all.

Mysticism, Connecticut

Halfway between New York City and Boston lies the aptly named harbor town of Mystic, Connecticut. The community is rich in history and features the Olde Mistick Village, an 18th-century reconstruction of a quaint New England village filled with period shops and charming eateries. Maritime enthusiasts can explore the Mystic Seaport, home to vintage clipper ships and museums, and the must-see Mystic Aquarium. For a slice of heaven, be sure to stop by Mystic Pizza. The local eatery rose to fame after being the inspiration for Julia Roberts’ romantic comedy of the same name.

Bar Harbor, Maine

The quiet coastal community of Bar Harbor, located on Mount Desert Island, is an enchanting destination known for its majestic coastal views, fresh seafood, and outdoor activities like whale watching and kayaking. Its backyard is Acadia National Park, which is lush with forests and lined with rocky beaches. A popular vacation spot for high society in the 19th century, the town’s historic charm is preserved in Mediterranean mansions, Tudor summer cottages, and Victorian-era bed and breakfasts. Dating back to the late 1800s, the walkable Shore Path stretches a half-mile through town, offering picturesque sunrise and sunset views over the harbor. Meanwhile, the quaint town center is lined with boutique shops and local eateries serving up mouthwatering Maine lobster.

Portsmouth, New Hampshire

Nestled along the Piscataqua River just north of Salem, Massachusetts, lies the picturesque harbor town of Portsmouth, New Hampshire. Dating back to the 16th century, the city combines Old World charm with a vibrant modern arts and culture scene. Historic buildings line the streets, along with jazz clubs, boutiques, art galleries, and a plethora of local restaurants. Explore one of New England’s most walkable cities on foot by taking a stroll along the waterfront and admiring the tugboats in the harbor. Then, head downtown for a relaxing afternoon window shopping at local boutiques. With beautiful beaches, quiet streets, and a thriving nightlife, there’s plenty to see and do in Portsmouth.

Woodstock, Virginia

As one of the oldest towns in Virginia, there’s much to love and learn about Woodstock. Nestled on one of the “seven bends” of the Shenandoah River, the picturesque village is rich in history from the Revolutionary and Civil Wars and is adorned with well-preserved historic buildings. There are plenty of hiking trails nearby for nature lovers, as well as a main street lined with urban delights like trinket shops and European-style cafes. Idyllic wineries like Muse Vineyards and North Mountain Vineyards and Winery surround the town, offering a peaceful setting to sip while taking in the beautiful mountain scenery of this Virginian paradise.

The takeaway meal

While sprawling cities like Boston and Hartford may get most of the glory on the East Coast, small towns are the heart of the Northeastern states. Away from the hustle and bustle of city life, there’s a range of small-town destinations that offer a peaceful break from everyday life. Whether you’re looking for a romantic weekend exploring covered bridges in the Vermont countryside or a hiking adventure in the peaks around Woodstock, Virginia, there’s something for everyone in New England.