7 of the Quirkiest Towns in New England

New England is an area in the northeastern corner of the United States, and it is composed of six states—Connecticut, Maine, Massachusetts, New Hampshire, Rhode Island, and Vermont. While these states are known for their rich history, beautiful coastlines, and scenic landscapes, a peculiar quirkiness sets the New England states apart from the rest of the United States. Steeped in folklore, legends, and ghost stories and home to very eccentric landmarks, be prepared to expect the unexpected when planning a day trip or weekend getaway to any of these quirky New England towns.

Wallingford, Vermont

Wallingford, Vermont, is a beautiful historic village on Route 7, surrounded by the peaks of Southern Vermont’s Green Mountains—a rugged and wild landscape of boulders, lush forests, and streams. Wallingford is a town steeped in mystery, and the looming mountains are known to hold quite a few dark secrets. One such tale recounts the discovery of a skeleton alongside a rusted gun barrel behind an old stone shop on Main Street. Speculation at the time suggested that the remains were that of a soldier from the French and Indian wars, but how he came to meet his fate has never been discovered. 

One of Wallingford’s quirkiest attractions is its “Boy and the Boot” statue, one of only a few Boy and the Boot statues worldwide. The statue, erected in 1898, is made out of cast iron, colorfully painted, and depicts a young boy holding a boot that eternally drips water from a small hole into a circular pool below. For years, the statue sat on the front lawn of the Wallingford Inn, but in 1910, the boy went mysteriously missing. The boy turned up again ten years later in the Inn’s attic. Since 1927, the statue has stood on the Inn's front lawn and serves as the symbol of the town of Wallingford. 

In 2023, the state produced over two million gallons of maple syrup, more than any other state in the US. Locals can choose from any number of producers in and around Wallingford, like Coles Mapleside Sugar House.

Jonesport, Maine

Jonesport, Maine, is a historic seaport town that boasts pristine beaches, spectacular views of the Atlantic Ocean, local culture, and chartered boat tours to hard-to-reach inlets and coves. Visitors can see seals basking on rocks in the hot sun, great blue herons flying overhead, and the historic and still-operational Moose Peak Lighthouse on Mistake Island. The vistas from the lighthouse are incredible, making it a memorable spot for a picnic lunch where you can relax and watch for birds and butterflies and smell the wildflowers. 

Any visit to Jonesport merits a stop at the unusual Maine Coast Sardine History Museum—a tribute to the lowly sardine—in the peaceful fishing town once home to at least 15 canneries. Exhibits at the museum include photographs, original sardine cans, labels, packaging, crates, letterheads, and more.  

Beals Island, accessible by the award-winning Beals Island Bridge, offers a laid-back lifestyle full of natural beauty. The bridge was opened in the summer of 2020 and is expected to remain in use for at least 100 years—25 years longer than the typical lifespan of a bridge. The island dates back to 1925 and is a paradise for photographers and artists. Nearby trails provide stunning views and are perfect for hiking, bird-watching, and biking.

Salem, Massachusetts

The town of Salem has embraced its spooky history with witch-themed shops, haunted tours, and museums. It's an excellent destination for those interested in the paranormal and Halloween enthusiasts. But lurking beneath the surface of ghosts, goblins, and things that go bump in the night belies a dark history.

The Salem Witch Museum is a famous local landmark that educates visitors about the Salem Witch Trials and attracts over 300,000 visitors annually. Perhaps inspired by the “witchcraft craze” that took hold of Europe during the 14th-17th centuries, where thousands of witches, mostly women, were executed, the Salem Witch Trials began when three young girls were purported to be experiencing “strange visions and fits.” A doctor diagnosed the girls with “bewitchment,” and so began what might be the equivalent of the modern-day “satanic panic.”. 

The historic House of the Seven Gables was built in 1668 and made famous in the 1851 novel by Nathaniel Hawthorne by the same name. Literature buffs will enjoy hearing about the house’s dark and ominous past. Today, the colonial mansion is one of New England's oldest surviving wooden mansions and is a museum showcasing furnishings, artifacts, and rare books from the period. 

Located along the Salem Habor waterfront, the Salem Maritime National Historic Site, established in 1938, preserves and interprets over 600 years of the maritime history of Salem—a major seaport in the late 18th and 19th centuries. The site covers nine acres of land, twelve historic buildings, and a replica of the tall ship Friendship. 

Woonsocket, Rhode Island

Woonsocket is a small Rhode Island town rife with quirky traditions, like exclusive sandwiches and a Chinese restaurant called Chan's Fine Oriental Dining, featuring a unique combination of jazz and eggrolls. This mill town, once thriving with industry along the Blackstone River, is now known for its historic dams, notably the Woonsocket Falls Dam.

The city retains a vibrant French Canadian culture, initially settled by French Canadians for millwork in the 1840s. Visitors can explore this heritage at the Museum of Work and Culture on 42 South Main Street, shedding light on Woonsocket's industrial past. While the museum covers history, it won't reveal the city's best-kept culinary secret—the “Dynamite” sandwich, similar to a Sloppy Joe, but served on a torpedo roll. The long-standing Ye Olde English Fish & Chips, open since 1922, offers a taste of traditional British-American cuisine. If nostalgia beckons, explore the third-generation candy store on the city's border—Pearls Candy & Nuts—filled with treats reminiscent of childhood. 

The Stadium Theater Performing Arts Centre & Conservatory, a rare Vaudeville Theatre era survivor, was built in 1926 and has hosted top-notch music, dance, and theater performances since its restoration in 2001. 

Mystic, Connecticut

Mystic, Connecticut, is renowned for its maritime history, offering a picturesque waterfront paired with a delightful quirkiness. At the Mystic Seaport, the nation's largest maritime museum, you'll encounter historic ships, a whimsical 19th-century village, and diverse naval exhibits. The town's allure extends to a charming drawbridge, eclectic shops, and the famous Mystic Pizza, featured in Julia Roberts' 1988 film. Mystic seamlessly blends nautical history with contemporary eccentricities, earning its reputation as a delightfully quirky destination in Connecticut.

Explore the shopping haven in Mystic, where commerce meets history in Olde Mistick Village. The village hosts over 40 shops and eateries in colonial-style buildings, providing a unique shopping experience amidst historical charm.

Mystic Seaport, a monumental maritime museum, is a testament to America's naval legacy. Visitors can tour a recreated 19th-century coastal village, historical ships, and a naval gallery, offering a captivating journey into maritime history.

The Mystic River Bascule Bridge is an iconic drawbridge spanning the Mystic River. This engineering feat has regularly opened with a distinctive counterweight design since 1920, creating a scenic and nostalgic view that adds to the town's quirky charm. 

Portsmouth, New Hampshire

Portsmouth, New Hampshire, nestled along the coast, is a town that fuses colonial history with a vibrant contemporary spirit, creating a uniquely eccentric atmosphere. Visitors can wander through the downtown center and Market Square, where independent bookstores, art galleries, peculiar boutiques, and an array of eclectic eateries are all within walking distance. Portsmouth's annual Halloween parade adds to the town's odd charm, attracting locals and visitors adorned in imaginative and offbeat costumes. 

Take in the historical oddities of Portsmouth at the Strawbery Banke Museum, a landmark that preserves homes and gardens spanning four centuries. Strawbery Banke provides an immersive journey through Portsmouth's ever-evolving architecture, culture, and daily life from the late 17th century to the mid-20th century. It's a quirky time-traveling experience that showcases the town's distinctive charm.

Prescott Park, a waterfront oasis steeped in history and beauty, provides some of the city’s most scenic walking paths and views of the Piscataqua River. But don't be fooled by its tranquility, as Prescott Park is a lively venue hosting unusual events, concerts, and outdoor theater productions every summer. 

Rockport, Massachusetts

This coastal town is known for its picturesque scenery and bohemian side. Bearskin Neck, a narrow peninsula in Rockport,  Massachusetts, features a mix of small shops, galleries, and seafood shacks on the waterfront. Wander down narrow streets, admire the picturesque views, and shop for unique gifts and souvenirs.

Motif No. 1, a famous red fishing shack, is a popular offbeat landmark on Bradley Wharf in Rockport. Often referred to as the "most often-painted building in America," Motif No. 1 has inspired artists and photographers for over a century and remains a symbol of Rockport's artistic community and maritime heritage.

Halibut Point State Park is a natural landmark known for its rocky coastline and granite quarries—remnants of the granite industry that was once prominent in the area. The park also features the iconic Halibut Point Lighthouse, providing a glimpse into the region's maritime history.

A Journey Through New England's Eccentric Charm

Discover the quirkiest towns in New England, each offering a blend of history, eccentricities, and unique charm. With dark secrets buried in lush landscapes, like the “Boy and the Boot” statue, the Salem Witch Trials, a museum devoted to the history of the sardine, “Dynamite” sandwiches, and an inspirational red fishing shack, these seven towns offer a delightful journey into the unexpected in the heart of New England.