7 Most Eccentric Towns in New England

While tourists may not know it, locals will tell you that New England is home to some of the quirkiest, most one-of-a-kind attractions in the country. Record-breaking giant arcades, massive 20-foot chair monuments, and century-old art colonies are just a few of the interesting experiences found throughout the region. Tired of the typical vacation spots and craving something a bit more unusual? These eccentric towns are sure to give you the weird and wonderful experience you have been seeking.

Laconia, New Hampshire

Home to the largest arcade in the world, a visit to Laconia, New Hampshire gives visitors the chance to unleash their inner child. Funspot Arcade is home to over 600 games, ranging from bumper cars and mini golf to claw machines and video games, covering just about every arcade game under the sun. After a morning at the arcade, travelers can spend the afternoon soaking in views on the Granite State Scenic Railway, which offers a 2-hour round-trip train ride that winds along the shores of Lake Winnipesaukee.

Also along the lake, visitors can enjoy some waterfront dining and seafood, Lobster in the Rough being a delicious restaurant to check out. Every June, Laconia puts on its annual Laconia Motorcycle Week, a town tradition since 1916 that welcomes around 300,000 visitors each year.

Westerly, Rhode Island

Visitors to the coastal resort town of Westerly, Rhode Island might be surprised by the popularity of its carousel. However, the Watch Hill Merry-Go-Round, dating back to 1883, holds the distinction of being the oldest operating carousel in the country, where children can ride for as little as $1. Regarding Westerly’s beaches, tourists and locals are often found sunbathing along the shoreline in the warmer months, with Misquamicut Beach and Watch Hill Beach being popular access points.

Westerly is also home to one of New England’s most historic lighthouses. Commissioned by President Thomas Jefferson himself, Watch Hill Lighthouse dates back to 1806 and is open in the summer months for visitors to see up close. Visiting during the winter months? There are still plenty of events going on. The Holiday Lights Spectacular, for example, is Southern New England’s largest holiday display and is free to the public, running through the end of January in Olde Mistick Village, which is just a 15-minute drive from downtown Westerly.

Provincetown, Massachusetts

Provincetown, Massachusetts, the country’s oldest continuous art colony, has attracted artists for over a century, inspired by the beauty of Cape Cod. Every year, artists apply to live in Provincetown’s Dune Shacks. This primitive and isolated community does not have running water or electricity, allowing artists to connect to their natural surroundings and further inspire their work.

To appreciate the work of these local artists, visitors must spend a morning at the Provincetown Art Association and Museum, home to more than 3,000 works from over 700 artists. Those looking to take a masterpiece home with them may want to explore the galleries on East End & Commercial Street, which features over 400 galleries that showcase local art. Between April and October, lucky visitors may have the chance to spot a humpback, fin, or right whale in the seas, with several companies offering whale-watching tours.

Freeport, Maine

Situated along the shores of Casco Bay, Freeport, Maine has made a name for itself among outdoor enthusiasts, thanks to its renowned outdoor outfitters and nearby natural attractions, such as the intriguing Desert of Maine. This desert is often seen as a contradiction to Maine’s lush forested ecosystems, home to 20 acres of sand dunes with a history dating back to the 19th century. On the premises, visitors can also camp at its well-kept campsites or enjoy a game of mini golf on the beautifully landscaped course. In need of camping gear? Visit L.L.Bean on Main Street, the store's largest location in the country.

Stowe, Vermont

Stowe, Vermont, is best known for its internationally acclaimed Stowe Mountain Resort, featuring 116 ski trails and Mount Mansfield, the highest peak in the state. In addition to downhill skiing and snowboarding, the resort attracts snowshoers and ice skaters and is regarded as one of the country’s top destinations for cross-country skiing.

Whether you want to travel in the chillier or warmer months, Stowe’s shopping district is the perfect pastime year-round, with local shops such as the Stowe Mercantile, Shaw’s General Store, and the Country Store on Main offering great gifts and souvenirs. For lunch with a view, Cliff House Restaurant is hard to beat, featuring floor-to-ceiling windows with views looking out over the surrounding alpine peaks.

Old Lyme, Connecticut

Founded at the end of the 19th century, the art colony of Old Lyme, Connecticut played a pivotal role in the development of American Impressionism. Visitors can explore this art style in depth at the Florence Griswold Museum, housed in a historic artist boarding house. Visitors can also attend events at the Lyme Academy of Fine Arts, which frequently showcases student work throughout the year.

For a night of jazz music, grab a drink at the Side Door Jazz Club, a jazz venue located at the historic Old Lyme Inn. Those wanting to head outdoors can enjoy one of Old Lyme’s 20 nearby hiking trails, located in preserves such as Jericho Preserve, Belton Copp Preserve, and Boggy Hole Preserve.

Gardner, Massachusetts

Towering over 20 feet tall and weighing more than 3,000 pounds, the Bicentennial Giant Chair stands prominently in the heart of Gardner, Massachusetts as one of the town’s most iconic landmarks. Due to its history of fabricating chairs, the city has been affectionately nicknamed the “Chair Capital of the World.” After grabbing a photo on the massive chair, visitors can find an incredible bargain at one of Gardner’s famed furniture outlets, such as Gardner Outlet Furniture or LaChance Interiors Inc.

Want to get some exercise? Spend an afternoon ice skating at the Veterans Skating Rink or kayaking on the lake of Dunn State Park. For a bit of entertainment, check out the Theatre at the Mount show calendar to catch a play put on by the students of Mount Wachusett Community College.

Final Thoughts

New England's quirky character and elaborate arts scene have flourished over centuries, perhaps largely thanks to being one of the country’s oldest settled regions. Artists and engineers have shaped the region’s creativity for hundreds of years, leaving their mark in both big cities and small towns. Whether you want to go on an art retreat or relive your childhood at a giant arcade, these seven towns may just bring out some creativity in you too.