Chester, Connecticut | Could You Live Here?

In very short order, we walked past a French restaurant and a British gift shop, both tucked along the sinuous Main Street in Chester, Connecticut. We, in turn, were passed by a Tour de France–attired cyclist intent on the horizon, smatterings of friendly locals, and a young girl riding a very tall horse. Who doesn’t yearn for a compact downtown that’s beautiful, friendly, and cosmopolitan, while hugging close its small-town New England character?

But let’s be clear—there’s fusty old New England and then there’s the slightly off-kilter version. Though settled in 1692, Chester is a bit Auntie Mame, with her “life is a banquet” feel to it—as if it’s constantly on the verge of something happening, which is pretty much true. This colorful 19th-century village, entwined with the rushing Pattaconk Brook, hosts a full dance card of high-spirited events to keep its 4,000 residents entertained: Winter Carnivale, Memorial Day and Halloween parades, a colorful Sunday farmers’ market, the Fourth of July Road Race, August’s Chester Fair (since 1877), and even a townwide tag sale in May.

It’s also an artists’ enclave. Wide sidewalks meander past notable restaurants and galleries, with plenty of room to accommodate baby strollers—a walking town that “draws creative people,” according to one shopkeeper, and a “great town for kids and dogs,” says another. But its roots are curled around history, too. Beginning April 1, the 1769 Chester–Hadlyme Ferry runs passengers over to eccentric Gillette Castle, dribbled onto its cliff like an oversized sandcastle. The Old Burying Ground creaks with tombstones from the 1700s, and the 1868 Chester Fife & Drum is one of the oldest continuously active such corps in the U.S. If, in a madcap Mame moment, you decide to join its ranks, the lessons, in true small-town spirit, are free of charge. They want more players.

The Setting

Just two hours from New York City and two hours from Boston, Chester settles into the nooks and crannies of hilly terrain on the banks of the Connecticut River, 10 miles north of Long Island Sound.

It’s an area riddled with water. Pattaconk Brook ducks under Main Street, threading its way through the village, a reminder of the waterpower crucial to its mill history. Breezy Cedar Lake has a large public beach on Route 148, just 2.5 miles from downtown, and Pattaconk Lake offers swimming and fishing in Connecticut’s second-largest state forest, Cockaponset.

The town itself is all curves, like a river, and it’s decked out like a riverboat with flags, balconies, and awnings. Six roads radiate from the center, where Simon’s Marketplace, the gourmet general store, is a focal point and gathering place.

“Solitude when you need it, engagement when you want it,” says resident Morley Safer of 60 Minutes. “Walden Pond meets Broadway.”

Social Scene

It’s clearly a dog-friendly town, as the abundance of fur testifies, so you’ll probably make friends easily with man’s best friend in tow.

If you opt not to join the Chester Fife & Drum Corps or the active Chester Historical Society (but don’t skip its engrossing Chester Museum at The Mill—the setting alone, with waterfalls and a view of Pattaconk Brook rushing toward town, is worth the price of free admission), do as longtime resident Donna Barnes suggests. Visit the charming stone Chester Public Library: “It’s teeny but well-established, or head for Simon’s, where everyone in town goes for morning coffee.”

Or plunge into the local music scene: Impressionist painter Leif Nilsson holds concerts in his Spring Street Studio & Gallery during the winter; come summer, the jam sessions move outside, into the artist’s backyard.

Eating Out

The smart thing would be to eat your way up one side of the street and down the other. Because if you do, you’ll experience a parade of creative chefery as well as gain a good sense of what the locals are growing.

Restaurant L&E, wrapped in coppery warmth, serves contemporary French in its intimate downstairs dining room; upstairs, its sister, The Good Elephant, melds Vietnamese with French. The Pattaconk 1850 Bar & Grille, festooned with flags, celebrates “the largest beer selection in the River Valley.”

Can’t choose between River Tavern’s crispy tofu and OTTO’s lamb meatball–ricotta–pecorino–mint pizza pie? No worries, it’s the same owner.

Shopping

The galleries up and down Main, Spring, and River streets promise to cover your walls or deck your halls with “curated” goodies of every persuasion—paintings, posters, photos, and more. Both Connecticut River Artisans and Maple & Main highlight the work of Connecticut artists.

Real Estate

Surprisingly affordable, the listings at the time of this writing included a prime downtown commercial building with a second-floor apartment, listed at $359,900. Within strolling distance to town, a circa-1925 three-bedroom home with heated garage was selling for $284,900.

Resident Perks

Anyone with musical leanings will appreciate the free lessons offered by the Chester Fife & Drum Corps. Expanding on the music theme, there’s the highly regarded Norma Terris Theatre, an offshoot of Goodspeed Opera House (in nearby East Haddam), where Broadway musicals get their start: more than 50 thus far, including 25 world premieres. And if you have an urge to check out Broadway itself, you can always catch the train to NYC from Old Saybrook, just 11 miles away.

Getting Your Bearings

Chester used to have its own inn, which means the timing is right for anyone who wants to open a B&B. Meanwhile, the Riverwind Inn in Deep River, about a mile and a half away, is a lovely and comfortable B&B; about 11 miles away, The Bee & Thistle Inn offers 10 pretty rooms in Old Lyme’s historic district, right next door to the Florence Griswold Museum.

This feature originally appeared in the March/April 2016 issue of Yankee Magazine.