7 Prettiest Towns In Connecticut
Connecticut packs a punch in all seasons: spring wildflowers and waterfall hikes, blazing foliage in fall, Long Island Sound beaches in summer, and cozy winter fun from ski hills to festive town greens. Add in centuries of history, and you’ve got a New England getaway that’s easy to love. In this list, you’ll bounce from Chester’s gallery-lined Main Street and nearby Gillette Castle views to Stonington’s beautiful lighthouse-and-harbor scenery. Here's our round-up of Connecticut's 7 prettiest towns!
Granby
In Hartford County, Granby is a charming town that offers an escape from the hustle and bustle of city life. The town has a population of just over 11,000 residents and shares a north-central border with the neighboring state of Massachusetts, making it a perfect location for a day trip. Granby is an excellent destination for nature lovers or those looking to spend time outdoors, as the area is surrounded by picturesque rolling hills and valleys. The town center, called Salmon Brook, is known best for the Civil War monument on display that was first dedicated in 1868.
One of Granby's most popular attractions is Enders Falls, in Enders State Forest. The waterfall sits at the end of an easy one-mile hike, with the Purple Blaze trail being a well-maintained, family-friendly way to see the stunning waterfall. Another great spot to check out is the Old Newgate Prison & Copper Mine. This seasonal museum allows visitors to visit the country's first chartered copper mine and the first state prison. You can also spend the afternoon at Old Mill Pond Village, which has shops, restaurants, Christmas decor, and family fun activities.
Chester
Chester, a charming small town in Connecticut, is beautifully situated on the west bank of the Connecticut River. Historically, it was home to the Wangums tribe, who lived alongside early settlers until 1785. Visitors often enjoy exploring the Old Burying Ground at the town hall, where the tribe's official cemetery is located, or visiting the Chester Historical Society housed in a lovely 19th-century mill. The town's downtown area is especially inviting, featuring a delightful collection of locally-owned shops, galleries, and cafes that create a warm and welcoming atmosphere. A favorite spot on Main Street is Honeycomb, an ice cream shop known for its unique homemade flavors and seasonal treats, making it a must-visit for locals and visitors alike.
The Cockaponset State Forest is easily accessible from Chester and offers plenty of outdoor activities, including hiking, fishing, and hunting. For a more laid-back experience, visitors can take a stroll on the Chester Creek Overlook or go for a scenic drive through one of the most beautiful routes in the town that leads to Brushmill by the Waterfall. Another incredibly popular location just a short drive away is Gillette Castle State Park, the former castle home for the stage actor who portrayed Sherlock Holmes.
Westport
Located along the beautiful Long Island Sound, Westport, Connecticut, is a charming town celebrated for its gorgeous beaches—some you can rent privately, and others that are welcoming to everyone. It’s a place that effortlessly blends elegance, charm, and breathtaking views along the Saugatuck River. If you're ever in the mood for some live entertainment, don’t miss the Westport Country Playhouse, a historic venue originally built in 1835 when it was a leather tannery. Today, it hosts fantastic theater productions, lively musical performances, and orchestra concerts that are sure to delight. Just nearby, you’ll find the Westport Museum for History & Culture, which features an intriguing exhibit about the celebrities who’ve called the town home over the years.
Nature enthusiasts can spend the day at Sherwood Island State Park, known best for being Connecticut's oldest state park. It's a great spot for a picnic, a walk along the water, or to enjoy a seasonal event. For visitors driving through the area looking for beautiful sights, the Green's Farm neighborhood of Westport is not only the oldest town but has delightful foliage in the Autumn, coastal views, and stunning winding country roads.
Colebrook
Colebrook, Connecticut, is a gorgeous town in the northwest corner of Litchfield County. The town is home to just over 1,000 people and is surrounded by wooded mountains and lakes, making it an ideal location for a peaceful weekend getaway. Colebrook was founded in 1779 and has kept much of its historical charm, with buildings dating back to the 1800s lining the town's roads today. A popular spot for visitors is the Colebrook Store, which serves as a general store for the town that sells groceries, deli items, and baked goods.
A top attraction in Colebrook is Soldiers' Monument and Memorial Park, celebrated for its scenic views, historical connection to local soldiers, and serene atmosphere for visitors. Another key site is Colebrook River Lake, which offers fishing, boat launches, and picnic spots. History enthusiasts can explore the Colebrook Center Historic District via a self-guided tour along Connecticut Route 183.
Ansonia
Ansonia, a visually striking town in Connecticut located on the west bank of the Naugatuck River, was incorporated in 1864 and has a population of just over 18,000. Known as "The Copper City" for its significant machine manufacturing industry in the Naugatuck Valley, this six-square-mile town offers numerous beautiful attractions. Notable sites include the Ansonia Nature Center, featuring a garden and hiking trails set in scenic surroundings, and Ansonia Riverwalk Park, which runs along the water and provides opportunities to observe wildlife and enjoy a tranquil environment.
For enthusiasts of historical architecture, Ansonia features the General David Humphreys House. This museum, previously the residence of George Washington's aide-de-camp during the Revolutionary War, offers guided tours of the 1699-built house. Visitors can explore its rich history and see artifacts from the era. Despite its modest size, Ansonia exudes vibrancy and offers beautiful scenery, making it ideal for a day trip or weekend escape.
Stonington
Situated on Connecticut's southeastern coastline, Stonington is a charming seaside town characterized by extensive farmland and historic stone walls. It is the only town in Connecticut directly facing the Atlantic Ocean, making it a distinctive destination with beaches, rural roads, charming villages, and beautiful farms all in one. Visitors can spend the day at Stonington Point, taking in scenic views of the lighthouse and Fishers Island Sound, or enjoy a leisurely drive through downtown, featuring restaurants like the popular Dog Watch Cafe.
A key attraction in Stonington is the Stonington Lighthouse Museum, established in 1840, offering stunning views of Long Island Sound. Located near Dubois Beach, it provides visitors with breathtaking scenes of Stonington Harbor. The blend of historic charm and natural scenery makes Stonington a popular spot for both tourists and locals.
Pomfret
Pomfret embodies a classic New England town, with rolling hills, babbling brooks, and historic architecture. Located in Connecticut's northeast 'quiet corner,' it offers a nostalgic experience of stepping back in time. Visitors can enjoy a self-guided walk through the town center, where colonial-style homes and landmarks like Pomfret Town House and Abington Congregational Church await. With a population of around 4,000, this small town also features several farms, making it ideal for fall apple picking at Lapsley Orchard or visiting the local farmer's market.
Pomfret boasts several natural attractions, such as Mashamoquet Brook State Park, with hiking trails, waterfalls, and a small swimming area. Another favorite among outdoor lovers is Wolf Den Land Trust, offering 13 miles of walking trails through forests and fields teeming with wildlife. With its charming small-town atmosphere and scenic natural surroundings, Pomfret is a perfect destination for anyone wanting to experience the genuine spirit of New England.
The charm and beauty of Connecticut's towns lie in their unique blend of history and scenic beauty. From the coastal vistas of Stonington to the New England charm of Pomfret, each town offers a distinct yet equally enchanting experience. Whether you're a history buff, a nature enthusiast, or simply seeking a peaceful retreat, these seven picturesque towns in Connecticut promise a beautiful journey through the state's diverse landscapes.
