7 Most Charming River Towns in Connecticut to Visit in 2024
History, culture, and natural beauty offer visitors a lifetime of memories in these seven Connecticut river towns. Each city boasts unique attractions, from Stonington's picturesque harbor and vineyards to Ansonia's industrial heritage and serene nature centers. Haddam's Goodspeed Opera House and Middletown's vibrant downtown reflect their cultural vibrancy, while Westport's Sherwood Island State Park and Simsbury's Farmington Valley Greenway cater to outdoor enthusiasts. Shelton's historic sites and lively Riverwalk add to the charm. Whether exploring well-known landmarks, enjoying outdoor adventures, or indulging in local culture, these towns offer something for everyone to discover in 2024 along Connecticut's scenic riversides.
Stonington
Stonington features a picturesque harbor, historic architecture, and pretty shops and galleries along the Pawcatuck River. Stonington Borough’s district features well-preserved 18th and 19th-century buildings, including the Old Lighthouse Museum. Built in 1840, the lighthouse remained in use until 1927. Visitors can climb the 29 circular steps to reach the top of the tower for a view of three neighboring states: Connecticut, Rhode Island, and New York.
Just outside the borough, Stonington Vineyards is a popular destination for wine enthusiasts. The winery offers daily wine tastings of its award-winning chardonnays, cabernets, and roses and tours of the vineyard and winemaking facilities. It's a great place to appreciate the serene beauty of the Connecticut countryside. Every Friday evening from July through August 2024, the winery sponsors a Summer Concert Series where visitors can bring a blanket and enjoy a relaxing evening of music and wine.
Haley Farm State Park is a 250-acre sprawling natural area along the Mystic River in Stonington. The park features miles of mapped walking, biking, and running trails with varied difficulty levels and bird- and wildlife-watching. Painting, drawing, and photography enthusiasts will enjoy pursuing their creativity in the town’s peaceful surroundings.
Ansonia
Along the west bank of the Naugatuck River, Ansonia boasts a rich industrial past, famous landmarks like the Ansonia Opera House, and outdoor recreation. Initially built in 1870 as the premiere theatre venue in the area, the building closed in 1971 due to the public’s waning interest in the opera but remains an iconic symbol of the city’s heritage. In 2021, the town hosted its inaugural paranormal convention, ParaConn, amid rumors of ghostly activity in the old Opera House. The event featured eerie attractions, including special guests, witchcraft displays, and psychic readings. The event returned in 2022 and 2023 in what the town hopes will spark an interest in reviving the old building.
At the scenic 150-acre Ansonia Nature Center, visitors can explore ponds and meadows, observe birds and wildlife, and enjoy hiking the 2.3-mile Ansonia Nature Center Trail Loop. The center also hosts educational programs, workshops, and events on environmental conservation and outdoor recreation. While “Every Day is Earth Day” at the Ansonia Nature Center, this year’s free Earth Day Festival takes place on April 20, 2024, where visitors can enjoy a farmer’s market, exhibits on the environment, live animals, music, local food, and more.
The Ansonia Harvest Festival in Ansonia takes place every September, and visitors can expect a wide range of events and activities to enjoy. From live music performances by local bands to delicious food vendors offering a variety of tasty treats, there is something for everyone.
Haddam
Haddam is on the east bank of the Connecticut River and home to the renowned Goodspeed Opera House—widely recognized as “The Home of the American Musical” by the millions of people who appreciate the art form. Goodspeed presents new and newly-revived musicals throughout the year during its season and attracts more than 130,000 musical lovers to the Connecticut River Valley. The 2024 season includes “The Mystery of Edwin Drood,” Rodgers & Hammerstein’s “South Pacific,” “Maggie: The Musical,” and the family favorite “A Christmas Story.”
Dating back to 1794, the Thankful Arnold House is a historic house museum dedicated to as much to Haddam's colonial past as it is to the sheer perseverance of women in the early 19th century. The museum offers visitors a glimpse into early American family life and showcases period furnishings, artifacts, and exhibits illustrating daily life during the colonial era. Explore the well-preserved interior, including the kitchen, bedrooms, and common areas, and gain insight into the lifestyles and traditions of the Arnold family.
The town offers scenic views and outdoor recreation opportunities. Visitors can enjoy fishing, boating, and birdwatching along the riverbanks or take a scenic cruise aboard the Connecticut River Valley's famous steamboats. The picturesque Haddam Meadows State Park stretches along the Connecticut River. It has a popular boat launch, so be sure to strap a canoe or kayak to the top of the car, pack a picnic lunch, and spend a leisurely day on New England’s longest river.
Westport
While Westport is known for its vibrant arts scene, with galleries, theaters, and cultural events galore, it also offers a variety of recreational activities, including boating and kayaking along the Saugatuck River. Sherwood Island State Park is Connecticut's first state park and the site of the 1939 World's Fair “Connecticut Pavilion." Sitting on the state’s stunning shoreline, the park’s easy access to Long Island Sound makes it a popular destination for visitors and locals who want to swim, play disc golf, or collect seashells from its sandy beaches. The park’s Sherwood Point is home to a 9-11 Living Memorial and Pavilion, which features a 9-foot long granite memorial stone set into a grassed area and oriented so that visitors face the Manhattan skyline.
Another great way to spend time outside in Westport is a day at Compo Beach—a scenic coastal area offering sandy shores, picnic areas, walking trails, and stunning views of Long Island Sound. It's perfect for swimming, sunbathing, paddleboarding, and even beachcombing.
Experience live theater at the Westport Country Playhouse, a classic theater that has been staging productions since 1931. Catch a play, musical, or special event featuring top-notch performances in a beautifully renovated venue. The 2024 season has just opened, and the line-up is fabulous with events like “An Evening with Judy Collins,” “All Things Equal: The Life & Trials of Ruth Bader,” “The Bacon Brothers Freestanding Tour,” and “An Evening with Fran Lebowitz.”
Simsbury
Along the Farmington River, Simsbury is a suburb of Hartford with a population of 25,000 and is considered one of the best places to live in Connecticut. Settled in the 1670s, Simsbury’s charming New England downtown is dotted with quaint shops, galleries, and restaurants housed in well-preserved historic buildings like the Maple Tree Cafe, a tavern built in 1895, or the Red Stone Pub located in a 1904 redstone building and host to numerous social events like “Trivia Tuesday,” “Wine and Whiskey Wednesdays,” and “Tall Tales and Tobacco Thursdays.”
The town has miles of hiking trails, a navigable river for kayaking, a rails-to-trails bike path, free bike rentals, two public golf courses, and more. The Farmington Valley Greenway is perfect for avid cyclists who want to bike along the scenic trail that stretches through Simsbury and neighboring towns. This picturesque multi-use trail provides a fantastic base for single or multiple days of off-road cycling, interspersed with quiet stretches along local roads.
One of the highlights is the 28-mile "Loop Ride" along Greenway's Farmington Canal Heritage Trail and Farmington River Trail. Renowned as one of New England's premier rides, it offers flat terrain, stunning scenery, and rich historical significance. Connecting five towns, this route provides ample opportunities to immerse yourself in the unique charm of each community along the way.
Middletown
On the Connecticut River, the 370-year-old city of Middletown offers a bustling downtown area with numerous eclectic shops like a “bark-ery” selling pupcakes and all-natural dog treats, a vintage clothing and streetwear store, and an eco-friendly lifestyle shop. As a testament to the city’s commitment to community, there’s a family-friendly board game cafe, a marshmallow factory, and restaurants serving Mexican, Asian, and Italian-inspired cuisine. Running through Middletown, the Mattabesset River provides a tranquil escape with many activities to explore the great outdoors, including hiking, fishing, and birdwatching.
Wesleyan University–the prestigious liberal arts college with over 3000 students from all over the world–plays a significant role in the community of Middletown. It hosts numerous cultural events, including art exhibitions, theatrical performances, lectures, and concerts featuring student and professional artists throughout the year. Middletown has a population of 50,000 residents and is also the home of Middlesex Community College, so approximately one-fifth comprises students.
The Wadsworth Mansion at Long Hill Estate is a historical landmark surrounded by beautiful gardens and lush landscapes. The mansion is open for walking tours every Wednesday from 2 - 4 PM, 2024, with docents on hand to answer questions about the history of the estate.
Shelton
Nestled along the Housatonic River, Shelton is the home of the Wiffle Ball, invented in the state in 1953. Today, over 60 million white plastic balls are played in backyards, school gyms, and playgrounds on every continent in the world. The signature yellow bat is made in the bordering state of Massachusetts.
Visitors to Shelton can explore parks along the river and visit historic sites like the Shelton History Center, which has been collecting the community’s history for over 50 years. Guided tours of the site, including the Brownson House, dating back as early as 1720, the Trap Falls School, a former one-room schoolhouse built in 1872, and the 19th-century Wilson Barn, are available throughout the year. The center's grounds also serve as a community social hub and hold events like the annual Vintage Vehicles Antique & Classic Car Show held in June 2024 around Father’s Day.
The Shelton Riverwalk is a scenic trail that follows the path of the Housatonic River, where visitors enjoy views of the river, wetlands, and wildlife as they walk, jog, or bike along the picturesque route. Indian Well State Park is also on the Housatonic River, and “Indian Well” is a popular spot for swimming, fishing, and hiking.
Exploring riverside towns in Connecticut offers a diverse array of experiences. Visitors can delve into rich cultural heritage, from iconic lighthouses to renowned theaters. Scenic vineyards and expansive state parks are popular with outdoor enthusiasts, while charming downtowns boast unusual shops, cafes, and restaurants. Guided tours of significant sites provide insights into local history, while riverside trails are perfect for leisurely walks or bike rides. Whether savoring award-winning wines, attending summer concerts, or enjoying water activities along the riverbanks, each town promises a unique and memorable adventure.
