6 Whimsical Towns to Visit in New England
The much-loved region known as New England comprises six states: Connecticut, Maine, Massachusetts, New Hampshire, Rhode Island, and Vermont. Renowned for its charming small towns, breathtaking fall foliage, and scenic coastlines, New England offers something for every type of traveler. Whether you're a nature lover seeking rugged mountains or someone who prefers sandy beaches and quaint seaside villages, the region’s landscape is as diverse as its attractions. So pull up an iconic Adirondack chair, sit back, and get to know six whimsical towns that are perfect for a visit in 2024.
Montpelier, Vermont
Voted No. 7 in USA Today’s “10 Best Small Towns in the Northeast for 2024,” Montpelier is the smallest state capital in the United States. The town’s Vermont State House, easily recognizable by its gleaming golden dome, was built in 1859 and remains one of the oldest and best preserved in the country. Located in an area called the Capitol District, the Vermont History Museum, Supreme Court Gallery, and the Vermont Arts Council are all within walking distance, where visitors can learn more about the history and art of the state.
Behind the capitol building, birders can discover Montpelier’s crown jewel, historic Hubbard Park, and nearby North Branch River Park, where ruby-throated hummingbirds, woodpeckers, warblers, and wood thrushes call the park home. Go bird watching, hiking along the riverbank, or mountain bike up Roll Call or Sapsucker trails for the thrilling coast down. The town hosts several quirky, whimsical events throughout the year, like “Ice on Fire,” where locals get together for sledding, hot chocolate, and a Christmas tree bonfire, and “All Species Day,” where visitors come dressed as their favorite species, and October’s “Enchanted Forest” celebration of music, fire, storytelling, and enchantment.
Woodstock, New Hampshire
Woodstock, New Hampshire (not the famous Woodstock) is a small town with 1,500 residents in the rugged White Mountains region on the northeastern coast of New Hampshire and Maine. It is so close to the neighboring town of Lincoln that it is sometimes called “LinWood” by the locals. Stroll downtown on Main Street to discover its one-of-a-kind shops, like the family-owned 1896 Fadden’s General Store & Maple Sugarhouse, Fig Tree North featuring local art and healing jewelry, and All Jammed Up. Visit the Woodstock-Inn-Brewery for a backstage pass to tour the new 30-barrel brewhouse.
The Lost River Gorge & Boulder Caves is a whimsically “gorge-ous” natural attraction where visitors can follow a one-mile wooden boardwalk trail along the Lost River to glacial boulder caves and a stunning waterfall. Climb the Giant Bird’s Nest for a view as far as the eye can see, or follow the Forest Adventure Trail to discover the treehouse and suspension bridge. During the winter, head back to Woodstock for Ice Castles—a must-see attraction where visitors escape into a world of fairy-tale ice caves, tunnels, slides, and frozen waterfalls.
Bethel, Maine
A classic New England town with two quirky Guinness World Records: in 1999, Bethel was the home of the World's Tallest Snowman, and then in 2008, the town beat its original record by building the World's Tallest Snowwoman. Bethel is an outdoor lover’s paradise all year round, with plenty of hiking, biking, and skiing opportunities, thanks to its unique locations between Sunday River and Mt. Abram Ski Area. Mt. Abram offers a more laid-back experience with 560 acres of skier-and-snowboarder-friendly terrain. From September 21 to October 13, 2024, Sunday River hosts River Fest, a series of whimsical weekend festivals like Maine Brew Fest, Flannel Fest, Fall Fest, and the dog-friendly Ruff Mountain weekend.
For even more adventure outside, head to nearby Grafton Notch State Park, tucked in some of Maine's most spectacular mountains, the Mahoosuc Range. With lots of rugged terrain for backcountry hikers, the park includes twelve of the most challenging miles along the entire Appalachian Trail, like the Old Speck Trail, which ascends to Maine’s fourth-highest peak at 4,170 feet, full of stop-and-stare scenery along the way and a spectacular view from the summit.
Mystic, Connecticut
Visitors will want to spend more than a day in the historic seaport town of Mystic, home to the famous Mystic Seaport Museum, where millions of visitors have walked the wooden deck of the 1841 Charles W. Morgan whaling ship. Stroll through the re-created seaport village and imagine the life of a 19th-century coastal New Englander. Explore the funky shops and eateries in downtown Mystic, tucked alongside colonial-era homes, churches, and landmarks like the iconic 1922 Mystic River Bascule Bridge—a drawbridge connecting Mystic with Stonington, where visitors can climb the 29 steps of the Old Lighthouse Museum, built in 1840, to see three states from the tower’s top: Connecticut, Rhode Island, and New York.
A must-see spot is the Mystic Aquarium, where families can see the only beluga whales in New England, African penguins, fish, frogs, and more. Follow it up with a visit to the whimsical, brightly-colored pink Alice in the Village Tea Room for tea and treats. Finally, ward off any evil spirits on September 21 to 22, 2024, at the town’s annual Garlic Festival 2024, where farmers, artists, and musicians will display their food and crafts along the path to Olde Mistick Village.
Martha’s Vineyard, Massachusetts
An island community just off the coast of Massachusetts, Martha’s Vineyard is a whimsical destination full of scenic beaches, lighthouses, and six charming villages, including Oak Bluffs—a magical town renowned for its gingerbread cottage style of architecture. Known as “The Campground,” where 19th-century Methodists would worship, the original tents were replaced by colorful wooden cottages. Today, there are over 300 storybook cottages and the landmark Iron Tabernacle that visitors can visit or the Cottage Museum to book a tour. For a different take on local history, the Flying Horses Carousel is the oldest platform carousel in the U.S. It was originally built in Coney Island in 1876 and moved to Oak Bluffs in 1884.
For boutique shopping and restaurants, head over to Edgartown, wander downtown, and have lunch at Among the Flowers Cafe, followed by homemade ice cream at Mad Martha’s. It’s only a 10-minute walk to the Edgartown Harbor Light for spectacular views of Edgartown Harbor.
Westerly, Rhode Island
A two-hour drive from Boston, Westerly is a nostalgic step back in time. A must-see for beach lovers is the Misquamicut State Beach, the state’s most popular beach with a half mile of beachfront. Further down the coast, overlooking Block Island and the tip of Long Island, beachgoers will discover Atlantic Beach Park, a charming landmark since 1921. The main attraction was the 1915 Herschell-Spillman Carousel, which sadly retired in the summer of 2024 due to the unpredictability of storms along the Atlantic coastline.
If it’s whimsical carousels visitors are after, look no further than the Watch Hill Flying Horse Carousel, the oldest continuously operating carousel in the United States, dating back to 1876. The carousel is located in the Westerly neighborhood of Watch Hill, once a mid-19th-century summer destination for the wealthy families of Providence; the area still retains much of its Gilded Age glory. Bay Street is the shopping district where shoppers find everything from chic boutiques to souvenir t-shirt shops flogging Taylor Swift merch (as the singer famously owns a “cottage” on Watch Hill).
Summary
Visiting any of these six whimsical New England towns is like revisiting wonderful childhood memories. The young-at-heart won’t go wrong with a trip to Mystic, a tour of storybook cottages on Martha’s Vineyard, or a nostalgic turn on the oldest operating carousel in the United States. From Montpelier’s quirky local events to Woodstock, New Hampshire’s “gorge-ous” setting, to the small town of Bethel, Maine—on the map for setting the world record for the tallest snowpeople—hop in the old wood-paneled station wagon, fill up the tank, and travel back to simpler days.
