8 Of The Most Captivating Small Towns In New England
New England is a historically rich region with stunning mountain landscapes popular among winter sports enthusiasts and coastal areas that will beckon beach and water lovers. The wide range of small towns in the region seems to definitively capture the aesthetic and appeal of New England. These eight towns are among the most captivating in New England due to their historical significance, rich cultural heritage, and vibrant destinations.
Towns like Mystic and Portsmouth represent the pivotal maritime industry that has buoyed many of these seafaring villages for centuries. Others, especially in Vermont, are known for their jaw-dropping foliage in the Fall when the leaves change colors in amazing ways. Whether you're looking for a rustic retreat or an upscale weekend getaway, these are the best spots in New England that stand out in a region renowned for its captivating towns.
Mystic, Connecticut
Historic Mystic was settled in the 1650s and rose to prominence by building over 600 ships in over 134 years, starting in 1784. Today, much of this history is interpreted at various museums, including the Mystic Seaport Museum. The destination also features a pleasant downtown district, where numerous other cultural attractions can be found.
The historic district is an eclectic blend of sea captains' homes and modern amenities, including restaurants like Milestone, serving contemporary American fare. The Whaler's Inn is in the heart of the district and is an excellent choice for those wanting to stay downtown. The boutique inn features 47 luxury rooms across five distinctive buildings with views of the iconic Bascule Drawbridge.
Stowe, Vermont
Stowe is a captivating four-season destination in Vermont, set against a backdrop of natural beauty and offering unparalleled experiences. A quintessential New England town, its covered bridges should not be missed by any visitor, including the 1964 Brookdale Bridge. Arts and culture are mainstays in the village, encompassing everything from galleries to live events.
Several art galleries are within walking distance of Main Street, including Bryan Fine Art Gallery. The gallery features a curated collection of work from New England artists. No trip is complete without visiting the nearby Ben and Jerry's Factory in Waterbury. Tours are available to see how the iconic ice cream is made, and visitors are encouraged to visit the Flavor Graveyard, where retired flavors are honored with humorous headstones. Meanwhile, Stowe Mountain Resort is a winter destination for skiers looking to sail through powdery snow on majestic Mount Mansfield.
Woodstock, Vermont
Woodstock is a rustic, historic, and artistic village in Vermont, and one of the most captivating in New England. A prime example of the area's artistry is on display at The Art of Craft Inc., an artisan-owned and operated gallery where guests can mingle with the local artists. Heritage sites are popular here, and no one should pass up the opportunity to see Vermont's only national historical park, the Marsh-Billings-Rockefeller National Historical Park.
The park features an elegant brick mansion and embodies several generations of conservationism. To complete the sophisticated and charming village atmosphere, book a room at the sophisticated Woodstocker Bed and Breakfast. The modern farmhouse-style inn is in the heart of the village and features nine guestrooms and suites.
Portsmouth, New Hampshire
Portsmouth is a historic seaport in New Hampshire, located on the Piscataqua River. It embraces the rugged maritime spirit of New England. What makes the port city so captivating is its collection of historical sites and modern attractions, making it a memorable destination for all. The community's preservation efforts are evident at sites like the iconic Strawberry Banke Museum. The outdoor history museum is among the most extensive in the region, spanning an entire neighborhood and allowing guests to witness the monumental changes that have occurred over the last 10,000 years.
Unique finds in town include the G. Willikers! Books and Toy Shop downtown, where shoppers are encouraged to test out the collection of toys before making a purchase. After exploring downtown, visit the Governor John Langdon House, built just after the American Revolution and brimming with history, defining Portsmouth's prestige in the region.
Kennebunkport, Maine
Kennebunkport is a picturesque coastal city in Maine, renowned for its historic architecture, stunning heritage sites, and walkable downtown area. Along with relaxing at Goose Rocks Beach, the area is known for fun activities, such as the nearby Vinegar Hill Music Theatre in Arundel. The theater is set in a barn setting, providing an intimate venue for multiple shows throughout the year.
The Seashore Trolley Museum offers a fascinating glimpse into another side of the hamlet, as well as the largest collection of electric railways in the world. Tours are available that explore the collection of railway cars that have been collected from all over the U.S. No trip is complete without visiting Maine's most photographed house, the 1825 Wedding Cake House. The striking residence earned its moniker for its white trim over yellow paint, built by a renowned shipbuilder, adding a tangible view into Kennebunkport's maritime history.
Bar Harbor, Maine
Bar Harbor is a quintessential New England town, featuring classic architecture and a walkable downtown area that is among the best in the state. The port town is known as the gateway to Acadia National Park, which lends an air of outdoor adventure to the downtown district that blends seamlessly with the cultural attractions. There are several art galleries to peruse, each featuring local art, such as Liz Cutler Fine Art, that add a unique flair to the area.
Bar Harbor has long been considered a summer vacation hub, and there are many inns to consider for an incredible experience in town. Sand Bar Cottage is a few steps from historic West Street and offers several cottages that embrace the maritime motif of the surrounding area. Landmark restaurants, such as Havana, that define the downtown district. Havana features fine dining and seafood, all with a Latin twist.
Newport, Rhode Island
Newport is known for its Gilded Age mansions, vibrant culinary scene, and maritime history. The mansions were the summer homes of the rich during the "Roaring 20s" and reflect the opulence of that era. Two of the most popular are the Breakers and the Marble House. There are several ways to discover these homes, including a chauffeured excursion from Newport Classic Car Tours.
The mansions are near a stunning nature trail known as the Cliff Walk. The trail offers panoramic views from the top of the cliffs. It is the only National Recreational Trail located within a National Historic District in the United States, adding to its charm. Although there is no shortage of interesting things to see and do, visitors can also find seclusion in Newport for a peaceful retreat. This dichotomy is part of what makes this seaside village so spectacular.
Provincetown, Massachusetts
Popularly known as "P Town", Provincetown, Massachusetts is a fun and vibrant city with a community that knows how to have a good time. It was where the Mayflower made landfall in 1620, commemorated in the Provincetown Museum, and today it is known for its LGBTQ+ friendliness. Many gather in the entertainment district to celebrate this fact at the annual Carnival in August.
P Town celebrates its cultural and artistic heritage in numerous galleries throughout town, including the Adam Peck Gallery and the Alden Gallery, both located on Commercial Street. The first features notable works by local artists who have been landmarks for over 15 years. The latter gallery showcases distinguished work from several artists in rotating exhibits, each adding a unique vibe to the area. This town is one of the most culturally diverse in the region, offering numerous reasons to book a trip to this popular summer destination.
New England is a fantastic region to visit at any time of the year, and these eight quintessential towns prove why that is. Whether looking for a ski destination in the winter or a rustic retreat in the fall, these hamlets are among the best in the region. Each one is a treasure trove of history, culture, and fun entertainment districts, which only adds to their charm.
Woodstock is an ideal place for a relaxing getaway, while P Town has a vibrant nightlife. This dichotomy of activities in the area is another fascinating aspect of New England. There is something for every traveler, any time of the year. If you are planning a trip to New England, these captivating towns should top your destination list.
