8 Quirkiest Connecticut Towns You Didn't Know Existed
Connecticut is mostly known for its stunning fall foliage, Yale University, and classic colonial architecture. As one of the original 13 colonies, Connecticut is a place teeming with American history. However, if you want something a little out of the ordinary, there are also quite a few surprises in the Constitution State. From flooded cities and uninhabited islands to recreations of old seaside villages in Mystic, Connecticut, it also has a quirky side. So, skip the conventional and explore the oddball corners of Connecticut! You’re sure to make new friends along the way.
Mystic
What many outside of Connecticut may not know is that the community of Mystic from the 1988 film Mystic Pizza is a real place! Even though the movie wasn’t technically filmed in Mystic, you can still visit classic Mystic Pizza recreations in the area, and even grab a slice of pizza at Mystic Pizza on Main Street. However, there’s so much more to this seaside community than just its movie references.
One of the more popular spots in Mystic is the Mystic Aquarium, where you can do more than admire sea creatures from inside their aquariums. It has exhibits where you can pet stingrays, and it’s the only aquarium in New England with Beluga whales. And who doesn’t immediately feel joy when they see a Beluga whale? When you want to learn a little more about Mystic’s maritime past, be sure to stop by the Mystic Seaport Museum. It’s more than a stuffy museum; it’s an entire recreation of the original seaport village, with historic ships, authentic reenactments, and vintage cobblestone streets. It almost feels like stepping back in time!
Marlborough
The small community of Marlborough is New England charm at its finest! With beautiful views of Lake Terramugus and charming parks like Blish Memorial Park in central Marlborough, it’s a great place to escape the bustle of the bigger cities. What makes Marlborough unique is the surprises you’ll find downtown! The most popular attraction in Marlborough is The Shops at Marlborough Barn. Every inch of this rustic barn is packed with unique finds from antique furniture to homemade crafts and gifts. If you can imagine it, you’ll likely find it in this quirky roadside attraction.
Just outside of town, you’ll find offbeat stops, like the Farm at Carter Hill. Think rusted cars on the lawn, outdoor pianos, and so many friendly goats! Or, you can stop in the Marlborough Tavern, a refurbished former stagecoach built in the late 1700s that serves up classic American fare and cold brews.
Brooklyn
The small village of Brooklyn is located in eastern Connecticut, not too far from the Rhode Island border. It’s a community known for its agriculture, most notably its bison. The Creamery Brook Bison Farm is a great place to shop for fresh meats, take wagon rides, and see the free-range bison roam. The farm is more than just a meat market and holds anticipated annual events like the Festival at the Farm, which showcases craft vendors, live music, wagon rides, and fantastic food trucks.
What makes Brooklyn unique is that it’s home to the Brooklyn Fair, which is one of the oldest agricultural fairs in the country. It started in 1809 as a modest community event and has since become one of the state's most anticipated summer fairs. It has carnival rides, zucchini races, chainsaw carving demos, and antique tractor parades. If you want to learn more about this hidden gem of Connecticut, be sure to swing by the Brooklyn Historical Society Museum.
Roxbury
In western Connecticut, far removed from the noise and traffic of the bigger cities, is the offbeat village of Roxbury in the seclusion of the Litchfield Hills. It’s a beautiful blend of historical ruins and manicured gardens with an offbeat artsy vibe. One of the coolest attractions in Roxbury is the Mine Hill Preserve, a natural wonder that weaves the tale of Roxbury’s iron mining past through the ruins left behind from the late 1800s. This 360-acre preserve features old stone ruins, blast furnaces, and rock quarries, with markers along the trails that explain their original purpose and historical significance.
Another notable attraction in Roxbury is the Kelsey Museum and Sculpture Garden. The garden hosts indoor exhibits, but nothing compares to its stunning outdoor sculpture garden. Amid blooming wildflowers and manicured gardens are contemporary sculptures that add a spiritual element to the walking paths, making it a must-see while in Roxbury. After a long day of exploring the offbeat sites of the area, nothing tastes better than a cold brew from Mine Hill Distillery, serving up craft spirits in a converted 19th-century mill.
Barkhamsted
Nestled among the greenery of the Litchfield Hills in northern Connecticut is the village of Barkhamsted. While there's plenty to see in the area, the most fascinating part isn't what you can see today—it's what used to be there. At the bottom of the Barkhamsted Reservoir (a reservoir created in the 1940s to supply water to Hartford) is Barkhamsted Hollow, the original town. Unless you packed your scuba gear, exploring the original town is impossible. When the water supply in the reservoir is low, you can see some of the old stone walls and original structures peeking over the surface. The Center Schoolhouse survived the flood, but the local historical society moved the building to Center Hill Road, where you can still visit it today!
Another unique peek into Barkhamsted’s past is the serene Lighthouse Village located nearby. No visit is complete without a visit to Lighthouse Village. It was a culturally diverse community with residents of African, Native, and European descent. The village no longer stands, but you can explore the ruins within the American Legion State Forest.
Branford
East of New Haven is the seaside town of Branford, known for its stunning coastal scenery and small-town vibes. It’s a great place to relax at Stony Creek Beach with a good book, but the real adventure in Branford lies just off its shores at Thimble Islands! The Thimble Island Cruise takes you on a tour of the cluster of nearly 100 islands. Money Island is the most unique of all the islands. While it has everything you’d find in a small village— a post office, grocery store, and library— no one lives on the island year-round.
Traveling inland to central Branford, you’ll find the Legacy Theater, formerly known as the Stony Creek Puppet House. It opened in 1903 as a silent theater and then shifted into a puppet theater in the 1960s. The venue closed down in the 2000s due to code violations, but it was purchased and cleaned up, and now serves as the Legacy Theater with live performances. And if you love beer, you have to check out the Caius Farm Brewery. It's Elagabalus brew, which won a silver medal at the World Beer Cup, making it a must-try for beer connoisseurs!
Chester
Along the shores of the Connecticut River, inland from coastal Connecticut, is the welcoming village of Chester. The winding city streets are home to delightful shops like the Space Chester and the Leif Nilsson Spring Street Studio and Gallery, which display everything from fine art to truly eclectic finds. Chester’s diners are classic New England—rustic and packed with personality, like Simon's Marketplace, with a vintage style and bistro tables set outside on the sidewalk. The Villager is another hidden treasure in Chester, known for its amazing omelets.
One of the neatest things to do outside of casually shopping in its artsy downtown area is to hitch a ride on the Chester-Hadlyme Ferry. The ferry service, which started in 1769, shuttles visitors across the Connecticut River. Today, there are better ways to cross the Connecticut River, but the ferry still operates as a way to take in the stunning views of this unique New England retreat.
Norfolk
In northern Connecticut is Norfolk, a small village with a big heart. The entire town looks like a scene from a storybook! There are colonial-era brick buildings with steep roof peaks, accented by ivy and flowers planted along the sidewalks. It has classic New England staples, like charming general stores like the Berkshire Country Store, and lovely public parks like Memorial Green, which also serves as a World War 1 memorial. However, it’s not its old-world charm that makes Norfolk unique— it’s the lively music scene!
There are quite a few places you can catch a live show in Norfolk at the Music Shed, a historical building constructed in the early 1900s by E.K. Rossiter (who also designed Steinway Hall in New York City!). It hosts classical music events throughout the year and is also home to the Norfolk Chamber Music Festival. If you prefer something a little more laid back, Infinity Music Hall is a local favorite in Norfolk. It opened in 1883 and was part opera house, part barbershop, and part saloon. Today, it operates as a cozy and dreamlike concert hall where you can watch live shows showcasing everything from jazz to indie rock!
Cozy up to Connecticut’s Quirkiest Hideaways
On the outside, Connecticut may seem buttoned up—maybe even a little stuffy. If you head beyond the tourist retreats, you’ll realize it has a weird side! And sometimes, the best adventures lie in places you’d never expect. They may boast that usual New England charm, like white church steeples, covered bridges, and winding mountain roads, but it’s the unusual details hidden inside that make them unique. From old puppet theaters to abandoned mining operations nestled in the forest, the best adventures are in places you’ve never heard of before— until now. So, explore these hidden hamlets before everyone else catches on!
