The Best Small Towns In New England To Chill Out 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. Renowned for remarkable fall foliage, maritime playgrounds, and Old World architecture, the delights of these small-town gems hold endless adventures. From the bewitching cobblestone streets of Salem, Massachusetts, to the picturesque waterfront of Portsmouth, New Hampshire, there are plenty of enchanting locales fit for a relaxing East Coast retreat.

Salem, Massachusetts

Just north of Boston, the bewitching town of Salem is brimming with spooky lore. Home to the infamous 1692 Salem Witch Trials, it is a popular Halloween destination, beckoning visitors from all corners of the world. Local museums like The Witch History Museum and historic homesteads like The Witch House offer a deep dive into the town’s haunting history. After learning about the origins of the 1600s witchcraft hysteria, visitors can pay 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 spellbinding shops packed with mystical trinkets and treasures. Fans of Hocus Pocus can visit its famous filming locations like Old Town Hall, The Ropes Mansion, and The Old Burial Hill Cemetery. Cloaked in colonial charm and magical allure, Salem is sure to put a spell on you.

Sleepy Hollow, New York

Less than an hour by train from New York City on the cusp of New England proper lies Sleepy Hollow. Named after Washington Irving’s classic spooky tale, “The Legend of Sleepy Hollow,” the fabled village is a fall favorite, especially around All Hallow’s Eve. While you won’t find the Headless Horseman galloping through town, the Sleepy Hollow Cemetery features a statue of the eerie equestrian and is the final resting place for Irving himself. During the month of October, Halloween lovers can delight in haunted happenings like the SUP Witches Festival and the Haunted Hayride. Full of historic buildings, 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 gorgeous gardens. For a quiet, storybook-like retreat from the Big Apple, Sleepy Hollow is the perfect destination.

Stowe, Vermont

At the base of Vermont’s highest mountain, Mount Mansfield is stunning Stowe. A popular ski and snowboarding destination, the mountain resort town boasts picturesque views, historic buildings, and a vibrant arts and culture scene. The natural landscape is especially breathtaking during the fall when the foliage is bursting with autumnal colors, and in the colder months when the snow transforms the town into a winter wonderland. Brimming with Old World charm, there are three classic covered bridges in Stowe, including the eerie Emily’s Bridge, which is said to be haunted by the love-scorned spirit of Emily. Apt for romantic mountain getaways and retreats rich with New England history, Stowe has you covered.

Mystic, Connecticut

Resting halfway between New York City and Boston is the aptly named seaport village of Mystic, Connecticut. Rich with history, the community features the Olde Mistick Village, an 18-century re-creation of a quaint New England village packed with period-era shops and charming dining locales. Maritime enthusiasts can explore the Mystic Seaport, which is home to old-fashioned clipper ships and museums, and the must-see Mystic Aquarium. Be sure to pop into Mystic Pizza for a “slice of heaven.” The local eatery was made famous after inspiring the Julia Roberts romantic comedy of the same name.

Bar Harbor, Maine

Residing on Mount Desert Island, the quiet seashore community of Bar Harbor is an enchanting destination renowned for majestic coastal vistas, fresh seafood, and outdoor activities like whale-watching and kayaking. Its backyard is the Acadia National Park, which is lush with woodlands, 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-style mansions, Tudor summer cottages, and Victorian-era bed & breakfasts. Dating back to the late 1800s, the walkable Shore Path stretches a half-mile through town, offering picturesque sunrise and sunset views of the harbor. Meanwhile, the quaint downtown is lined with boutiques and local eateries boasting mouthwatering Maine lobster.

Portsmouth, New Hampshire

Sitting on the Piscataqua River just north of Salem, Massachusetts, lies the picturesque port city of Portsmouth, New Hampshire. Dating back to the 16th-century, the town combines Old World charm with a vibrant modern arts & culture scene. Historic buildings line the streets, along with jazz clubs, boutiques, art galleries, and an abundance of local restaurants. Explore one of New England’s most walkable cities on foot by taking a stroll along the waterfront to admire the tug boats in the harbor. Then, head downtown to spend a leisurely afternoon window-shopping at the local shops. With beautiful beaches, peaceful streets, and flourishing nightlife, there’s a little of everything in Portsmouth.

Woodstock, Virginia

As one of the oldest towns in Virginia, there’s a lot to learn and love about Woodstock. Resting along one of the “seven bends” in the Shenandoah River, the quaint village is rich in Revolutionary and Civil War history and adorned with well-preserved historic buildings. There are plenty of nearby hiking trails 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, providing a peaceful setting to sip while soaking up the gorgeous mountain scenery of this Virginian haven.

The Takeaway

While sprawling cities like Boston and Hartford may get most of the East Coast glory, the small towns are the heart of the Northeastern states. Beyond the bustle of city life is an array of bite-sized travel destinations that offer a peaceful pause in the day-to-day. Whether you’re craving a romantic weekend exploring covered bridges in the Vermont countryside or a hiking adventure in the peaks surrounding Woodstock, Virginia, there’s a taste of something for everyone in New England.