7 Most Eccentric Towns in New England

New England’s reputation for tidy villages and measured traditions misses an important truth: the region also excels at sanctioned weirdness. Small towns here turn local history into spectacle, then double down until it becomes identity.

A lakeside city can host a motorcycle pilgrimage that draws hundreds of thousands. An arts colony still sends creatives to live in dune shacks without modern utilities. Maine even has a “desert” built from a strange mix of geology and human land use. These eccentric places are the product of old institutions, stubborn pride, and communities that choose to preserve their quirks instead of sanding them down. The seven towns below show how New England stays surprising!

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 charming art colony of Old Lyme, Connecticut, has been a cornerstone in shaping American Impressionism. Visitors are warmly invited to discover this beautiful art style more deeply at the Florence Griswold Museum, set in a lovely historic artist boarding house. You can also catch inspiring events at the Lyme Academy of Fine Arts, which often features the incredible work of talented students throughout the year.

For a lively night filled with jazz, stop by the Side Door Jazz Club, a cozy venue nestled inside the historic Old Lyme Inn. If you love spending time outdoors, you'll be delighted to explore one of Old Lyme’s 20 scenic hiking trails, found in wonderful preserves like Jericho Preserve, Belton Copp Preserve, and Boggy Hole Preserve.

Gardner, Massachusetts

The Bicentennial Giant Chair, towering at over 20 feet and weighing more than 3,000 pounds, proudly stands in the heart of Gardner, Massachusetts, and is one of the town’s most beloved landmarks. Known as the “Chair Capital of the World” because of its rich history of chair-making, it's a must-see for visitors. After taking a memorable photo on this enormous chair, you can enjoy amazing deals at local furniture stores like Gardner Outlet Furniture or LaChance Interiors Inc.

If you're looking to get active, spend your afternoon ice skating at Veteran’s Skating Rink or kayaking on the peaceful waters at Dunn State Park. For some entertainment, be sure to check the Theatre at the Mount’s schedule to see a play performed by the talented students of Mount Wachusett Community College.

Final Thoughts

New England's distinctive charm and vibrant arts scene have developed over centuries, likely fueled by its status as one of the earliest settled regions in the country. For hundreds of years, artists and engineers have contributed to the area's creative landscape, leaving their influence in both bustling cities and charming small towns. Whether you're interested in an art retreat or nostalgic fun at a large arcade, these seven towns might inspire your own creativity.