7 Whimsical Towns to Visit in Connecticut

Although the New England state of Connecticut is known for its rich history and serious abundance of cultural and natural attractions, it still knows how to embrace its whimsical side. Travelers looking for a fun, lighthearted escape are in luck in Connecticut, which is home to a long list of interesting small towns that are ready to show visitors a good time. Whether you want to kick back and enjoy nature at a beautiful preserve or park or kick up your heels at a local festival, you will find it in Connecticut. Discover seven hometowns worth adding to your "must-visit" list.

Cornwall

Incorporated in 1740, pretty Cornwall is set in the foothills of the Berkshire Mountains and was dubbed the greenest town in Connecticut due to its abundant natural surroundings. The idyllic town is also situated among the Mohawk State Forest, which is known for its rugged hills, miles of trails for hiking and biking, diverse wildlife, and lush forest. Although Cornwall has a rich farming and industrial history dating back to the 1700s, and plenty of serious attractions and sites worth seeing, it maintains a whimsical, free-spirited feel.

You are in luck if you love outdoor adventures, as the area is ideal for fishing, all types of water sports, skiiing in the winter, and golfing, just to name a few. Climb up to the top of Mohawk Summit, which has an impressive elevation of 1,683 feet and is the highest point on the Mattatuck Trail. Anglers can spend a day on pretty Mohawk Pond, a 16-acre kettle pond that is stocked to the gills with largemouth bass. Do you love the romantic allure of covered bridges? The town is home to the West Cornwall Covered Bridge, which makes the ideal backdrop for photographs.

Mystic

Best known as the setting for the classic '80s hit movie Mystic Pizza, the fun, quirky town of Mystic stepped into the ship-building scene soon after it was founded in the mid-17th Century. Today, the quaint, scenic town, situated on the Mystic River, has the quintessential New England feel, complete with plenty of seaport charm.

Explore historic downtown Mystic while you are in the area, and discover a fun and vibrant collection of waterfront shops and eateries. You can sample freshly caught seafood at the family-owned and operated J&R Seafood Market. For dessert, satisfy your sweet tooth at Kenzie's Fudge and Chocolate Shop. If you love learning about local history, check out the historic Mystic Drawbridge, as well as a variety of sea captains' homes from the Colonial Era. Also, don't miss the Mystic Museum of Art or the Mystic Aquarium, both of which are fun for visitors of all ages.

Bethel

Beautiful Bethel's claim to fame is that it was the birthplace of the late, great circus ringmaster PT Barnum, and that piece of historical significance adds to the town's whimsical feel. Although it's just over 70 miles from New York City, Bethel is able to maintain plenty of small-town charm, as well as more than its fair share of green spaces and natural beauty. Let loose at one of Bethel's well-planned parks, including Meckauer Park and Bennett Memorial Park.

Take a stroll through downtown Bethel, where you will encounter adorable antique shops, farm-to-table eateries serving food made with regional ingredients, and cute cafes, including the mouth-watering Putnam House Restaurant & Tap Room. If you are a movie lover, the Greenwood Features Theater shows a mix of new releases, independent, and classic films.

Chester

The fun never ends in charming Chester, which plays host to a wide variety of fun special events all year long. Its rich and varied social calendar includes festivities such as December's Starry Nights Illumination Celebration, spooky Halloweentown, and weekly farmers markets. The whimsical town is also filled with natural delights, including nearby lakes, brooks, and even waterfalls. Appreciate nature during a trip to the nearby Cockaponset State Forest, where you will find miles of trails for hiking and biking, as well as a lake for fishing, boating, and other recreational activities.

Branford

Although picturesque Branford is located just over five miles away from the bustling city of New Haven, it has an idyllic, New England small-town vibe. Situated on the scenic Long Island Sound, Branford offers visitors 20 miles of beachfront, opportunities for hiking and biking on the 30-mile circular Branford Trail, which winds past wetlands and woodlands, and plenty of scenic roads for exploring the region.

Adults looking to have a good time while sampling local craft beer can head to Thimble Island Brewery, Stony Creek Brewery, or the Duvig Beer Company. Constructed in 1724, the Harrison House Museum gives history lovers a look into Branford's past with a vast collection of memorabilia.

Westport

Lovely Westport, which has long been known as a relaxing respite for New Yorkers looking for a break from city life, has both a quaint and cosmopolitan appeal. Visitors come from all over to experience the Westport Country Playhouse and the Westport Museum of History and Culture, as well as a variety of other fun and interesting attractions. Westport cs a touch of whimsy with its playful feel, as it perfectly straddles the line between urban and rural life.

Among Westport's long list of recreational and leisure activities are lounging on sandy Burying Hill Beach and strolling through the vibrantly colored and sweet-smelling Gilbertie's Herb Gardens in the spring and summer months.

Old Saybrook

Despite Old Saybrook's name, the town has a youthful feel, as well as unparalleled natural beauty, a rich history, and plenty of the famous New England charm to spare. Old Saybrook is well-known for being the former home of the world-renowned classic actress Katharine Hepburn and for being one of Connecticut's oldest towns. Settled in 1635, Old Saybrook is situated at the point where the Connecticut River meets the Long Island Sound, making it a water-lovers paradise. There are many nearby places where visitors can enjoy stunning water views and outdoor activities, such as the breathtaking Rocky Neck State Park and family-friendly Harvey's Beach. Get in touch with your playful side by checking out Mini-Golf at Saybrook Point or browsing quirky local shops such as Re-Unique.

From funky, historic towns teeming with quaint boutiques, cultural attractions, family-run eateries, seaports, and even pristine beaches to fast-paced, world-class cities, the picturesque state of Connecticut has it all. Visitors seeking a lighthearted, stress-free getaway, whether it be for a family summer vacation or a weekend respite, are especially in luck in this New England state. Not only do Connecticut's picturesque small towns have a warm and welcoming ambiance, but they also offer an abundance of fun activities to enjoy at any age or time of the year.