This Underrated Town in Connecticut Beats the Famous Ones

Set along the Connecticut River a few miles upstream of Essex and the Long Island Sound, the small town of Chester boasts the same New England charm as famous places like Mystic and New Haven, but usually without the crowds.

Settled by the English in the 1660s, Chester’s Connecticut River Valley location, midway between New York City and Boston, each just two hours away, is nothing short of idyllic. A former shipbuilding and milling center, the Connecticut River powered the town’s early growth thanks to its being a vital transportation hub for the Northeast United States.

Three centuries later, it’s still one of the prettiest small towns in Connecticut, a fact summed up by the late CBS reporter Morley Safer. A long-time resident of the town and a regular on 60 Minutes, Morley described Chester as having “Solitude when you need it, engagement when you want it. Walden Pond meets Broadway." And he was spot on with his assessment.

Explore Chester's Past

There’s no denying that Chester owes much to the presence here of the Pattaconk Brook. Flowing through town and in places buried beneath Main Street before joining Cedar Creek and emptying into the Connecticut River, it once powered the mills that in turn powered the local economy.

The Chester Museum at The Mill is an ideal first stop to learn more about the town and its rich history. Housed in an 1860s mill site adjacent to a waterfall and the Pattaconk Brook, two floors of exhibits showcase the evolution of Chester from its time as home to the Wangunk Indians through 300 years of development to the modern day (admission is free).

The Old Burying Ground (aka, Hearse Hill Cemetery) is another must-see point of interest in Chester. The oldest gravestones date back to the 1700s, with a section established in 1736 for the last of the Wangunk Indian tribe. The Chester Meeting House at 4 Liberty Street is another must-see, hosting concerts and community events in a historic setting.

Take the Old Ferry

The Chester-Hadlyme Ferry is another blast from the past that you’ll want to make time for. In operation since it was established in 1769, the ferry is a five-minute drive east of town and is one of the oldest continuously operating ferry services in the United States.

While not as old as the ferry service itself, the current vessel, the double-ended Selden III, was launched in 1949 and carries up to nine cars and passengers across the Connecticut River. Running from early April through to the end of November, it’s an ideal way to get to Gillette Castle State Park in Hadlyme. The views of the medieval-style castle perched on the hillside as you cross the river are priceless.

Other Things to Do in Chester

Main Street Chester has become a hotbed of artistic endeavor. Here, you’ll find classy boutique shops and galleries like the Lori Warner Studio/Gallery and Swoon with their local artworks and luxury gifts. The Chester Gallery also showcases Connecticut artists in a charming old Victorian parlor setting.

Blackkat Leather is another local business worth shopping at, and features handmade leather goods, locally made jewelry, and unique art. If you enjoy a good read, Montgomery & Taggert Bookshop on Water Street is Connecticut's first romance-themed bookstore and is fun to browse.

Speaking of reading, the Chester Public Library is a must-visit. The Chester Library Association dates to 1875, and today’s handsome stone library building continues that tradition in the center of town.

Eat, Drink, and Stay in Chester

There’s no shortage of local food and drink experiences within easy reach of downtown Chester. Grano Arso is popular with residents and visitors alike. Located on Main Street in an old bank dating from 1902, its Italian-inspired dishes go down a treat after exploring the town.

Other popular dining options include The Village Bistro with its locally and regionally sourced menu items and intimate vibe; and Otto, which serves wood-fired pizzas outdoors during warmer months. For an authentic old Chester setting, The Brushmill by the Waterfall on the outskirts of town is located at the historic Rogers & Champion Brushworks site. It’s a pleasant spot for its covered bridge, chestnut beams, and fireplace.

The town’s not without a cool adult beverage scene, too. Little House Brewing Company is a great microbrewery with a taproom and beer garden, and an ever-evolving tap list.

For an authentic old town accommodation experience, the historic Millhouse has been restored and is located just steps away from the Chester Museum at The Mill, making it an ideal base for wandering around town. While not a hotel, this two-bedroom apartment can be booked directly through the local owners.

Nearby Towns and Easy Side Trips

Essex, just four miles south of Chester, regularly appears on lists of America's most charming small towns. A highlight of a visit is the Essex Steam Train & Riverboat, a unique attraction departing from the town’s 130-year-old train station for a 12-mile ride that includes a cruise along the Connecticut River.

Even closer (it’s just three miles away), Deep River hosts the Deep River Ancient Muster in mid-July. The world’s largest fife and drum gathering has been held here since 1885 and attracts corps from around the world.

East Haddam, seven miles to the north, is home to the Goodspeed Opera House, the main stage of the famous Goodspeed. Another star attraction here is Gillette Castle State Park with its faux stone castle built by actor William Gillette, famous for playing Sherlock Holmes on stage.

Chester Delivers

While sometimes overlooked in favor of other Connecticut travel destinations, Chester has exactly what it takes for a fun New England getaway. Where else in the USA can you arrive aboard a 250-year-old ferry service, sample delicious food created by the chefs who own the restaurant, then visit art galleries run by the artists who create the work? Yes, Chester is an ideal dupe for the better-known tourist spots in Connecticut.