7 Playfully Peculiar Towns In Connecticut

Connecticut, as one of the original 13 colonies, played a significant role in the overall development of America. It boasts an incredibly diverse economy, leads in technology, and is home to prestigious educational institutions. But that is not all Connecticut has to offer. Its location, between New York City and Boston, makes it highly accessible to those seeking a respite in gorgeous surroundings. Connecticut is also very appealing to families, as it offers a multitude of fun, family-friendly destinations.

As such, the Constitution State draws millions of visitors every year. Some of these visitors don’t only go in search of the most well-known attractions, but also the little, peculiar places in between. If you want to visit a compact state that offers much more than you thought possible, make Connecticut your next travel stop in 2025.

Moodus

Moodus was once inhabited by Native American Algonquians, with the three tribes inhabiting the area being the Wangunks, Mohegans, and Nehantics. The village is located within East Haddam and is home to fewer than 2,000 people.

What you may not know is that Moodus is short for Machinmoodus. This translates to "the place with bad noises" in an Algonquian dialect. The "bad noises" refer to the rumblings or crashings that can be heard around Mount Tom, which sits in Machimoodus State Park. Scientists say that the noises come from micro-earthquakes, which are at the lower end of the Richter scale. The natives who once lived in the area believed the noises came from evil spirits. Either way, if you climb Mount Tom, you may experience the thundering sounds for yourself while enjoying majestic views of the Salmon River.

If you prefer to avoid noises from tiny tremors, you can visit the Thankful Arnold House Museum. The museum is a historical house once inhabited by Thankful Arnold, her husband Joseph, and their 11 children.

East Haddam is also home to the Little Red Schoolhouse, where American spy Nathan Hale once taught. And, you can visit Gillette Castle State Park, where the imposing Gillette Castle stands. The castle once belonged to William Gillette, who was best known for playing the role of Sherlock Holmes on stage.

If you want to enjoy a day next to the water, the East Haddam Town Beach beckons. It lies on the Moodus Reservoir and has lifeguards and a pavilion you can reserve.

Wethersfield

Wethersfield is all about life’s simple pleasures. The Wangunks lived here for many centuries before the pioneers built the first settlement, and life was not always easy. But today, visitors love getting ice cream at one of the many sidewalk cafes downtown or buying fresh vegetables at a garden shop, and just having a relaxing time.

If you’re up for something completely different, you can participate in Wethersfield’s quirky escape room adventure. Lara’s Labyrinth is unlike any other escape room. Here, you have to get into character, which means you will likely stumble across an abandoned cabin in an enchanted forest while hunting for food. You can choose between the Spellbreakers, Malediction, and The Dark Side adventures. Each of these has a 1-hour time limit (keep in mind that The Dark Side is not suitable for children).

Back in the sunlight, you can stretch your legs along the Connecticut River’s shore. You’ll find well-trodden paths here that wind past historic stone walls. It is also an excellent vantage point for bird watching. The Wethersfield Cove offers deep water access to the river, and was also once the home of the very first ship built in the state, the Tryall. Another adventure of a different kind awaits at the nearby Dinosaur State Park and Museum, where you can see dilophosaurus tracks left on a lake shore more than 200 million years ago.

Chester

Chester is the type of town you picture when you hear the word "quaint." The town is situated along the Connecticut River, offering authentic New England charm. Here, you can visit the Villa Bella Vista, an Italianate farmhouse at 7 Old Depot Road. Also called The Ledges, this structure was built on a hill that overlooks the river. The building features concrete and stucco walls, as well as a three-story tower that evokes the architecture of Northern Italy.

The Chester Museum at The Mill is another popular attraction. It is situated in an 1860s gristmill on Pattaconk Brook and features award-winning exhibits. These exhibits provide incredible information on everything from Wangunk origins to steamboats. There are also two 285-year-old millstones on display.

For those who are less interested in history and more interested in cuteness overload, the Chakana Sky Alpacas are ready and waiting at the nearby alpaca farm. At the farm, you’ll meet six machos and eight hembras. The farm owners are also expecting a couple of crias (alpaca babies) to be born during the summer and fall.

Plymouth

You may not run into adorable alpacas in Plymouth, but there are plenty of peculiar attractions to choose from. At the Lock Museum of America, you will discover the largest collection of keys, locks, and handcuffs in the world. There are eight rooms filled with exhibits, including a 4,000-year-old wooden lock that came from an Egyptian tomb. When you’ve toured the museum, you can check out the Lock Museum Adventure. This escape room features several clues for you to solve the mystery by opening locks and safes.

If you visit Plymouth just before Christmas, don’t forget to stop at Towill’s Christmas Tree Farm. Here, you and your family can choose and cut down the perfect tree while shopping for wreaths.

If you want to do something a little more active, the Hancock Brook Lake area is a 721-acre playground for the entire family. You can fish, kayak, and canoe, while keeping an eye out for beavers and herons.

Putnam

Putnam is another small town in Connecticut with big outdoor spaces. The Putnam River Trail, for example, is an excellent place to bike or jog. You will pass several parks and woodlands, and you can even roller skate all the way if you want to.

For some old-school entertainment, the Bradley Playhouse is open all year round. This historic theatre hosts live shows and has been restored to its 1901 glory.

If you or your children love comics, you should stop by Wonderland Comics in downtown Putnam. This comics and collectibles store is the biggest of its kind in Northeastern Connecticut. Whether you favor Marvel over DC or just want to read Archie comics, this place has everything you need. Meanwhile, at Jeremiah’s Antiques and Shoppes, you’ll find wonderful antiques at great prices. And, the attached museum is filled with celebrity costumes and movie props.

Putnam also goes big when it comes to festivals. The Great Pumpkin Festival, featuring a Zombie Fashion Show, is the best way to get in the mood for Halloween in October. And, the Holiday Dazzle Light Parade is the most festive celebration on the town’s calendar. Santa arrives on a fire truck as glowing floats make their way through the charming small town streets.

Tolland

If you want level paths and extreme greenery when you go biking or hiking, there is no better place than the Hop River State Park in Tolland County. Tolland itself, a town of just over 14,000 people, offers more than 4,200 acres of open space. There are 45 miles of hiking trails, three fishing areas, and a disc golf course. You can even practice your archery skills here.

Tolland also offers several other attractions that lean more into the quirky side of the town. These include a visit to the Tolland Jail Museum. Here, you can step into a real 1856 jail cell and listen to the original bell tower bell at the Old Tolland County Courthouse Museum.

If you want to take home a souvenir from your Tolland travels, you can visit Birch Mountain Pottery. You will get a glimpse into a real, working pottery studio while you shop for finished pottery work in the showroom.

Noank

Noank is a small, sleepy coastal village that offers two Little Free Libraries, an old-timey barber shop, and a community garden. The village lies at the mouth of the Mystic River, where wooden boats bob in the water and restaurants face the Long Island Sound.

Ford’s Lobster is one of the most famous restaurants in Connecticut, not only because of the excellent lobster. It is also featured in the Julia Roberts movie, "Mystic Pizza."

Noank is also home to Argia Mystic Cruises, which offers family-friendly sailing adventures that start at Mystic’s Bascule Bridge. Another family-friendly activity is participating in the town's Memorial Day Parade, one of the longest-running parades in the country.

Christmas time is when Noank shines. As the temperatures drop on Christmas Eve, people join the Luminiaria Stroll. The streets are lined with candles, a tradition started by resident David Blacker many years ago. The Santa Claus and Carol Singing event features Santa in a fire engine and a merry group of carolers who visit homes to sing for families.

Conclusion

Each of Connecticut’s playfully peculiar towns has something wonderful to offer visitors and families. The state is doubling down on what makes it special, so from 2025 onwards, you’ll find even more attractions to enchant you in the small towns here. Whether you plan to visit for a weekend or you find a place you want to stay forever, even the smallest corners of the state will surprise you in the best way possible.