8 Of The Most Eccentric Towns In Connecticut
Besides its rich history, fascinating fall foliage, and charming coastal beauty, there's much more to the New England state of Connecticut. In fact, there is a lot to discover beyond its postcard-perfect landscapes and colonial past. While most tourists are used to the quaint, laid-back, and almost faultless facade of its small towns, dig deeper and you'll come across low-key communities with traditions that defy the concept of normal. Their personalities, quirky, unconventional, and delightfully offbeat, showcase a side of the Constitution State that many tourists didn't expect.
From attending a medieval-themed festival in Lebanon to hunting for paranormal activities in Southington, Connecticut, is home to places that go against the norm without fear of rebuke or ridicule. Whether you're a curious traveler or a local looking for something unexpected, Connecticut is home to eight of the most eccentric towns you'll likely every come across.
Uncasville
This tiny village in the town of Montville, New London County, hosts one of the most eccentric festivals in New England. At the Mohegan Sun Expo Center, residents celebrate the Connecticut Pickle Festival, which features everything pickles. Participants indulge in pickle-themed fun and activities, from sampling pickle martinis and taking pickle shots to eating pickle pizza and drinking Kool-Aid pickles. You also get a Pickle Eating Contest and the popular Pickle Juice Challenge, while the Pickle Pablo Mascot is always on hand to entertain the young festival goers.
Beyond its pickle festival, Uncasville is home to the country's oldest Native American-owned and operated museum. A tour of the Tantaquidgeon Museum exposes the story and heritage of the Mohegan tribe, with tours conducted by Native tribe members. Furthermore, you can take a trip down memory lane at the Fort Shantok Archeological District, a Native American historic site dating back to the 17th century.
Wethersfield
This small town in Hartford County promises guests one of the quirkiest escape room experiences in the country. Wethersfield is home to the infamous Lara's Labyrinth, an elaborate escape that thrusts guests into an alternate world of fantasy, mystery, and adventure. Participants have to get into character and venture down a series of abandoned cabins with challenging puzzles and fun themes. Each experience lasts about one hour and is curated for kids and adults alike. The Webb Deane Stevens Museum allows tourists to travel back in time to the 18th century in a period mansion that pays tribute to the American spirit. Meanwhile, those who wish to reconnect with nature can visit the Eleanor Buck Wolf Nature Center for a rich lesson in ecology and native wildlife species.
Southington
About 65 miles from Stamford, classic horror film fans and paranormal investigators visit Southington to relive one of the most chilling scenes in movie history. This vibrant town in Hartford County is home to the Snedeker House, which earned its infamy after the claims of paranormal activity and ghostly activities by the Snedeker family. This led to an attempted exorcism in the 1980s, which inspired "The Haunting in Connecticut." Today, it retains its eerie feel, and a dark cloud seems to hover over it, although there haven't been reports of hauntings by subsequent owners.
A pint of freshly crafted beer at Witchdoctor Brewing Company promises to shake off the fright and relax your mind after the paranormal tour. Alternatively, you can take a relaxed picnic on the pristine shores of Crescent Lake to revel in the paradisiacal scenery or dips in the water.
East Haddam
This quaint village in Middlesex County stands out from the crowd with its unusual townscape, punctuated by quirky architectural attractions. It is famous for hosting the Gillette Castle, whose rustic and medieval appearance turns heads. Rising high above the Connecticut River, the 24-room mansion was designed by the celebrated American actor and playwright, William Gillette, who portrayed Sherlock Holmes. This only adds to the allure of the 184-acre property, with guests coming to admire the rough building design and to explore the story behind it.
The Goodspeed Opera House is another architectural spectacle along the Connecticut River. Sporting a conspicuous white facade, this popular cultural hub has staged various theatrical presentations since the 1870s, birthing iconic musicals, such as Shenandoah and Annie. East Haddam boasts a rich natural scene and invites first-timers to take advantage of birdwatching and hiking opportunities in the serene wilderness of Devil's Hopyard State Park.
Plainville
Plainville boasts a vibrant downtown district that houses a thriving business environment with plenty of family-friendly entertainment venues. However, the laughter can easily turn into a scream for families visiting the Witch's Dungeon Classic Movie Museum. This unusual location exhibits a collection of movie props and life-size wax figures that bring life to classic movie monsters. The facility pays homage to characters and effects artists who contributed to the fantasy film legacy. While it is a low-key fun experience, you can always expect a gasp or yelp here and there.
Paderewski Park is the go-to spot for outdoorsy visitors in Plainville, offering a serene green space with grassy lawns and walking trails along a pristine pond. Meanwhile, one of the best times to visit the town is during the annual Plainville Fire Company Hot Air Balloon Festival, which draws hundreds of high-spirited attendees.
Rocky Hill
About 35 minutes from New Haven, Rocky Hill earns a mention among the most eccentric towns in Connecticut thanks to the motherlode of prehistoric treasures it houses. This quaint river community is known for Dinosaur State Park and Arboretum, which attracts dinosaur enthusiasts and other curious tourists year-round. The 80-acre site is believed to harbor one of the country's largest dinosaur tracks, believed to originate as far back as 200 million years. Besides the footprints, guests can also browse interactive exhibits and rare fossils, providing a vivid glimpse of the Mesozoic era.
There are more archaeological discoveries to make at Dividend Pond, which offers a charming blending of historical ruins and spectacular natural beauty, featuring a 28-foot waterfall. Finally, remember to board the Rocky Hill-Glastonbury Ferry for a laid-back cruise down the calm Connecticut River to soak in the pleasant scene.
Union
Nothing seems to be going on in this sleepy Tolland County village until you get to this one-of-a-kind diner, 31 miles from Hartford. Union is home to the Traveler Restaurant, known to serve delicious burgers and seafood, but with a twist. After a meal, patrons receive up to three books of their choice as part of the meal package. The best part about eating here is that bibliophiles can turn it into their personal library and indulge their love for reading books after a hearty meal in a welcoming atmosphere.
Despite its small population, Union boasts a rich heritage dating back more than 290 years. Its captivating backstory is preserved and shared by the Union Historical Society, where you can peruse a vast catalog of archives, photos, and artifacts. Meanwhile, outdoor lovers make the most of a 516-acre playground at Bigelow Hollow State Park, which opens doors to picnicking, hiking, fishing, camping, and other adventures.
Terryville
This adorable village in Litchfield County impresses visitors with its New England charm and a one-of-a-kind museum. The whimsical Lock Museum of America displays an extensive collection of locks, some dating back to the early ages. It features around eight rooms full of keys, handcuffs, locks, plates from safes, padlocks, and a curious 4,000-year-old wooden lock from an Egyptian tomb. Besides the exhibits, guests can indulge in the Lock Museum Adventure, a unique escape room experience where you have to solve complex puzzles in the form of safes and locks.
The Eli Terry Jr. Waterwheel is a vital landmark in the town and offers a unique perspective of 19th-century industry and engineering. Meanwhile, those who wish to step outside can relax by golfing at Pequabuck Golf Club.
From Rocky Hill's prehistoric fossils to Union’s bibliographic restaurant, these eccentric towns in Connecticut prove that the best experiences await where you rarely expect. Each quirky destination offers a unique blend of history, creativity, and local charm that defies the ordinary. Whether you're drawn to odd museums, whimsical architecture, or one-of-a-kind festivals, these towns invite you to explore an alternate world bursting with oddities in the United States. So pack your curiosity and take the scenic route to Connecticut’s most eccentric spots.
