7 Most Beautiful Small Towns In Connecticut to Visit in 2024
Connecticut is one of the New England states with unique landscaping, encompassing elements from more northern areas with an urban influence from southern neighbors like New York and New Jersey. The state is known for its lush hills, meadows, and coastal shores, along with over 5,000 miles of riverfronts and streams to enjoy. Each town in Connecticut has its own blend of landscapes and natural attractions that offer different views from season to season. If you’re looking for some of the most beautiful views in Connecticut, be sure to add these seven small towns to your next travel itinerary.
Ashford
Nestled in the ‘Quiet Corner’ of Connecticut in Windham County is Ashford, a historic town dating back to 1714. Ashford has just over 4,300 residents and features rolling hills, thick forests, and farmland throughout its 38 square miles. Yet, even with its quiet and remote location, this town is centrally located, making it easy to commute to surrounding cities like Hartford or schools like the University of Connecticut, which is under ten miles from Ashford. This quaint town is also home to the Ashford Dairy Bar & Grill, a well-loved summer ice cream shop that has been a mainstay for over 50 years. The shop is also a short drive from the Henrietta House Bed and Breakfast, a one-of-a-kind lodging spot offering homemade breakfast and cozy rooms.
The Henrietta House Bed and Breakfast is positioned along the Josiah Trust Forest, with a peaceful walking trail called the Josiah Byles Trail. This area of protected land has meadows, the Byles Brook, and even beaver dams, where some lucky visitors may be able to see the animals hard at work. Some of the other outdoor attractions in Ashford include the Nipmuck Trail, the June Norcross Webster Scout Reservation summer camp, and the River’s Edge Sugar House. The maple farm is located right on the Mount Hope River and is open year-round, serving syrup, honey, and locally made items.
New Canaan
New Canaan is a town in Fairfield County known for its relaxed atmosphere and picturesque neighborhoods. It is conveniently located between Connecticut’s capital city and New York City in the panhandle section of the state, making it easy to travel to any of the surrounding areas. There’s a significant focus on the arts and community in New Canaan, which has helped the town gain its reputation for being not only a wonderful vacation spot but also fantastic for those who want to relocate to the Constitution State. No matter your interests, New Canaan has a wide selection of outdoor attractions that shine a light on the area’s beauty, as well as indoor locations that are just as visually impressive as they are educational. The Carriage Barn Arts Center is one spot that embodies all the elements that make up this town through its art exhibit and musical performances.
The abundance of preservation centers and well-maintained parks make New Canaan ideal for nature lovers and anyone who wants to truly experience the charm of New England landscapes. There’s Grace Farms, a humanitarian organization set on 80 acres of land, where guests can relax and marvel over the unique architecture, as well as Waveny Park, a historic park that has a garden, walking trails, and dog-friendly areas. Some additional attractions include the New Canaan Farmers Market, open Saturdays from April to December, and the New Canaan Nature Center, complete with a botanical garden and events throughout the year.
Farmington
Farmington, located in the heart of central Connecticut, is a town rich in colonial history. There are approximately 26,000 people who live in Farmington, and the landscape is made up of thick oak forests, open farmland, and some wetlands. Rattlesnake Mountain, an incredibly popular location for its views, is also located in Farmington. There are several routes visitors can take to reach the top of the mountain, though Will Warrens Den and the Metacomet Trail are the two most frequented. These hikes can be completed in just a few hours' time and are of moderate difficulty level. The Farmington Canal Heritage Trail is another loved location, especially for the foliage during autumn, and runs through Connecticut to the Massachusetts state border.
Those who want to learn more about Farmington’s history while exploring the town can stop at the Stanley-Whitman House museum to see the home dating back to 1720. Guests can explore the gardens on the grounds, pay respects at Memento Mori Cemetery, and gain an inside look into the historic village green. There’s also the opportunity to see the town’s natural sights at the Hill-Stead Museum, a revival house and art museum. House tours are offered daily, though visitors can schedule private tours for Saturdays. In addition to the museum, the organization hosts events, like the outdoor performing arts series, which are held on the incredibly well-maintained grounds.
Coventry
Tolland County’s small town of Coventry has just over 12,000 residents and, like many of the other cities on this list, has a robust history. The town’s reputation is tied to being the birthplace of Captain Nathan Hale, who today has numerous buildings named after him throughout Coventry. The Captain Nathan Hale Monument is a peaceful place where guests can visit and see the 45-foot obelisk in person, while the Nathan Hale Homestead Museum offers tours through this 1739 property. The home has been restored to highlight what life was like during Hale’s life, most specifically during the Revolutionary War. Guided tours are available on weekends, though the grounds are open year-round for visitors.
Creaser Park stands out as one of the town’s best outdoor locations. It is dog-friendly and has hiking trails, picnic tables, a disc golf course, and fishing in the Skungamaug River. There are 2 miles of hiking trails split up along four different pathways, each offering different views and terrain difficulty. The Coventry Farmers Market is another beloved attraction in town, and it operates on Saturdays from June through October. The market is held on the elegant grounds of Hale Homestead, and each week, there is a different theme or event. Coventry also has two vineyards with tasting rooms, the Cassidy Hill Vineyard and Dragonfire Meadery.
Lebanon
Lebanon is a tiny farming town nicknamed the ‘Heartbeat of the Revolution’ due to its involvement in the war. Today, the town is known for its rural atmosphere and rolling hills that make up Lebanon’s 55 square miles of land. There are also over 150 farms in Lebanon, though it is still centrally located to larger cities like Willimantic and Norwich, which offer a larger selection of commercial attractions. Yet, there are plenty of charming attractions right in town that encompass all the elements that make rustic New England so appealing. Travelers and residents who want to learn more about this historic town can visit the Lebanon Historical Society Museum and Visitors Center located on Trumball Highway. This organization holds numerous events throughout the year, informative exhibits, and a museum gift shop.
The Lebanon Green is another beautiful outdoor area that’s truly unmatched by any other green on the East Coast. The green, which is just under one mile long, perfectly meshes modern-day manicuring with classic elements like stone paths found during the American Revolution. This location is best for walking during the warmer months and ice skating during winter. Mooween State Park is another outdoor recreation area with over 500 acres for hiking, mountain biking, or just relaxing in the water. This state park sits on Cedar Lake and has no admission charge for guests, making it a great spot for travelers to experience this town’s beauty.
Essex
Situated along the Connecticut River is Essex, a charming town with impressive landscapes and a population of roughly 6,800 people. This town, named a ‘Perfect Small American Town’ by 1,000 Places to See Before You Die, boasts beauty throughout every season, offering beautiful summers on the water to the snow-covered historic village during winter. The colonial architecture lining the streets only adds to the charm and creates the perfect opportunity to stroll Main Street and Main Street Park, two areas with benches, shady areas to enjoy the scenery, and several options for shopping and dining along this quaint section of town.
One of the best ways to take in all the beautiful sights Essex has to offer is by visiting the Essex Steam Train & Riverboat. First opened in 1971, there are several ways for visitors to encounter the town, from a train or riverboat ride to a dinner train event or unique experiences based on the season or holiday. The Connecticut River Museum is a great way to mesh an afternoon of seeing some natural landmarks with learning about the historical aspect of the area’s maritime culture. The Connecticut Valley Railroad State Park, where the Essex Steam Train & Railroad departs, is another ideal attraction for getting outdoors and enjoying the beauty, especially for families with children. The park area of this location has picnic tables along the water and a small cafe where guests can grab a quick snack.
Shelton
Shelton is a bustling small town in Fairfield County with just under 42,000 residents as of 2022. This area is unique in that some sections of the city have fun and exciting attractions while the neighborhoods maintain a quiet and peaceful environment. One of the most well-known landmarks intertwined with the town’s history is the Housatonic River, which has over ten miles of shoreline and several ways to see the water views. Visitors can take a walk to the downtown riverfront area to see the Ousatonic Dam and gate locks or stop at the Shelton River Walk to stroll along the river and through Veteran’s Park. Another stunning park in Shelton is Indian Well State Park, a peaceful location with a public boat launch, picnic spots, and hiking trails.
The Shelton Lakes Recreation Path is a simple hiking trail that’s appropriate for beginners, bike riders, and strollers. This trail connects Huntington Center to the downtown section of Shelton through an 8.4 round trip path, featuring a mostly paved trail, though a small section is made of stone. Families can also spend time at the Sports Center of Connecticut, which sits on nearly 20 acres of land. There’s no shortage of fun activities at this sports complex, as there are dedicated areas for mini golf, an indoor driving range, laser tag, ice skating or hockey, and bowling.
Whether you’re looking to relocate to Connecticut or just want to experience all of the incredible beauty this state offers, these seven small towns are filled with natural elegance. Each area has unique landscapes and one-of-a-kind attractions that make this state different from others in New England. From streets lined with some of the oldest buildings in the country to miles of salty coastline, there’s no shortage of beautiful areas to visit in 2024.
