7 Storybook Towns In Connecticut

With some of the prettiest waterfronts, oldest historic districts, and best postcard scenes in the country, New England shines as one of the top travel destinations in the United States. Connecticut is no exception, its storybook towns enchant all who stop by. No matter the season, from coastal beach communities to inland mountain towns, Connecticut distinguishes itself with its natural beauty. Coupled with historic architecture, captivating museums, and endless recreation, the charms of this New England state are unparalleled.

East Haddam

In the Connecticut River Valley, East Haddam’s iconic castle and waterfall are straight from the pages of a fairytale. Not to be confused with the neighboring town of Haddam, this river town transports its visitors to a world outside Connecticut, beginning with its medieval-inspired mansion. Gillette Castle State Park is perched 200 feet above the Connecticut River on 7th Sister Hill, its landmark “castle” attracts upwards of 300,000 visitors annually. The 14,000-square-foot stone fortress can be toured along with its surrounding 184-acre woods.

Devil's Hopyard State Park is the perfect follow-up, and despite its name, this natural attraction is heavenly. The scenic park was established in 1919, gaining its name from Colonial legends attributing the symmetrical potholes near the park’s waterfall to the devil’s footprints. Today, geologists theorize these mysterious holes were formed by the friction of stones caught in circular currents, but the folklore certainly adds an air of intrigue. Visitors can hike to experience the stunning 60-foot Chapman Falls and its legendary potholes followed by the park's other highlights, including a charming covered bridge and numerous vistas.

Essex

Around twenty minutes south of East Haddam, Essex is another Connecticut River Valley town with a classic New England feel. Described as “A Small Town Where History Lives On” by the New York Times, this historic seaport village is brimming with frozen-in-time charms. Throughout the village, Federal and Victorian-style homes are a staple, with highlights like the Essex Town Hill which dates back to 1892. Visitors can also stop by the Griswold Inn on Main Street. Whether grabbing a bite or booking a stay, this delightful landmark has welcomed visitors since 1776.

Elsewhere in town, the Pratt House is one of Connecticut’s oldest surviving structures. With sections of the building believed to date back to the 1600s, today, people can visit this remarkable landmark with a guided tour on Fridays, Saturdays, and Sundays. For waterfront views, the Town Dock and Connecticut River Museum are lovely next stops. Housed in a historic 1878 warehouse, the museum allows visitors to discover a world of maritime history and explore the river aboard a seasonal RiverQuest eco-tour. Every May, the museum is also the final meeting point for their Annual Burning of the Ships Day parade. This quirky festival commemorates the pivotal event in 1814 when the British burned an estimated 27 to 28 ships in the Essex harbor.

Westport

With the largest river and ocean waterfront in the state, Westport offers a more beachy escape. The town sits along the scenic Long Island Sound, an estuary of the Atlantic that merges with the Saugatuck River. Ocean and river scenes can be enjoyed at local spots like Compo Beach, a 29-acre park with a year-round sand beach and boardwalk. With the addition of Mobi Mats, four wheelchair-accessible picnic pads, two wheelchairs, and a floating beach wheelchair, this accessible shore welcomes all.

Picturesque shorelines can also be enjoyed at Sherwood Island State Park, the first state park in Connecticut. The 235-acre park features a mile-long beach ideal for lounging and combing for shells. Beyond the sand, visitors can also enjoy a seasonal Nature Center and views of the salt marsh on the east side of the park. To the west, a disc golf course and picnic area also offer a break from the sand, along with several coastal forest walking trails.

Madison

A one-hour drive from Westport brings us to Madison, another gorgeous coastal town on the Long Island Sound. Thanks to its location—midway between Boston and New York City—Madison is a popular getaway spot, especially for those seeking refuge from the urban buzz. For beachgoers, Hammonasset Beach State Park takes the spotlight with two miles of sandy beachfront. As Connecticut’s largest shoreline park, there is plenty of room to go around, whether swimming, fishing, kayaking, or enjoying views from the boardwalk.

For educational fun, the state park is also home to the Meigs Point Nature Center. Here, people of all ages can learn about environmental preservation through a seasonal Touch Tank for up-close learning. The Center is also home to a range of native fauna, many of which cannot be released due to injuries. Currently, the Center cares for a variety of animals, including snakes, crabs, fish, and turtles. To see more of the habitats where these coastal critters normally thrive, Hammonasset is also home to a segment of the Shoreline Greenway Trail, a nearly-one-mile scenic hiking path.

Old Saybrook

Continuing east along the coast, Old Saybrook is a historic beach town perfect for those seeking a more laid-back getaway. For access to the waterfront, Harvey's Beach anchors the community, the 100-yard stretch of white sand charming all who visit. People staying at the Saybrook Point Resort and Marina can also experience the town’s fabulous waterfront, as well as a “signature blend of timeless ambiance and modern comforts.”

If you find yourself exploring the rest of Old Saybrook, this timeless atmosphere is inescapable. The town is home to over 100 historic estates and buildings, including gems like the Humphrey Pratt Tavern. This former tavern and stagecoach stop was built around 1785, making it one of Old Saybrook’s oldest buildings. By taking the Self-Guided Tour of Old Saybrook’s historic homes and sites, you may also stumble upon some of Old Saybrook’s countless antique shops. For those who love hunting for old treasures, spots like the Essex Saybrook Antiques Village, The Trove, and Estate Treasures of Old Saybrook can be explored for hours.

Simsbury

In Hartford County, Simsbury stands out for having some of the best storybook scenes in the state. Talcott Mountain State Park generally takes center stage with nature lovers, especially hikers seeking stunning vistas. The 1,000-foot summit is Simsbury’s top geographic feature, its panoramic views reaching as far as New Hampshire’s Mount Monadnock. Atop the mountain, hikers can also take on the 120-step climb up Heublein Tower. From its observation room, hikers are rewarded with even better views of the landscape below.

Back in town, Simsbury offers a different kind of jaw-dropping scene on a repurposed 19th-century bridge. Built in 1892, the 183-foot metal-truss bridge has since been transformed into a pedestrian and bicycle pathway. Now known as the Old Drake Hill Flower Bridge due to the dozens of flower boxes and baskets adorning it, the landmark is a popular photography spot and also makes for a lovely stroll. In addition to the flowers, the bridge offers fabulous views of the Farmington River below. While currently closed due to ongoing renovations, Simsbury's Director of Public Works hopes to have the bridge open by the start of the 2025 season.

Mystic

Returning to the coast, Mystic is one of New England’s top-rated towns, beloved for its maritime attractions and picture-perfect scenes. In 2023, the town ranked fourth in USA Today’s list of top US tourist destinations, attracting attention as the only New England town on the list. This historic seaport and shipbuilding hub sits on both sides of the beautiful Mystic River (connected by the Mystic River Bascule Bridge), and locals are proud to uphold its maritime heritage.

For obvious reasons, the Mystic Seaport Museum shines as the town’s brightest attraction. Here, guests can view a range of maritime artifacts including the world’s oldest surviving whaling ship, the Charles W. Morgan. Visitors can also discover the museum’s Henry B. DuPont shipyard, 19th Century Village and even explore the waters aboard one of the museum’s vessels once the season begins in the spring of 2025. For people of all ages, the Mystic Aquarium is a fun follow-up back in town, while adults may prefer an evening show at the Mystic Dark Room, an immersive performing arts theater.

Final Thoughts

Traveling to New England is an easy choice, but deciding which of its states to visit can be a bit trickier. If you are someone who loves a diverse range of attractions and landscapes, Connecticut will prove itself time and time again. Whether visiting fairytale towns like East Haddam for its enchanting landmarks, towns like Westport for its classic beaches, or towns like Simsbury for its awe-inspiring mountain vistas, Connecticut’s storybook communities will leave any traveler spellbound.