Chester, Connecticut

A boating family idles out of Chrisholm Marina toward the Connecticut River. Photo by Caryn B. Davis

Boating through Chester, Connecticut, some 10 miles upriver from Long Island Sound, is like traveling through an Impressionist landscape. The Connecticut River’s banks are lined by stately trees and the private docks of handsome homes, tucked amid the foliage. Wildlife abounds, and meandering side creeks, rich with the greens, browns and purples of cattail and pickerelweed, invite exploration.

Chester Chart


There are 4 marinas in Chester, all located some 1.5 to 2 miles from the downtown area. The closest are Chester Point Marina, Castle Marina and Hays Haven Marina. Just north of these is Chrisholm Marina, which offers a shuttle into downtown Chester.


To access the town’s eclectic shops and restaurants, you can bike or walk from the marinas or get a lift. Chester does not have a public dock, although you can anchor nearby and get pretty close to downtown by taking a kayak or dinghy up Chester Creek. The marinas will also try to accommodate you if you give them a call ahead of your arrival.



The heart of Chester is Simon’s Market, a family-owned breakfast, sandwich and gift shop on Main Street that has become the de facto meeting place for locals and a good place to grab a quick bite or something to drink. Another worthwhile stop is the Connecticut River Artisans Center, which offers a great selection of jewelry and crafts made by some of the best craftspeople in the valley.

Restaurant owner and chef Jonathan Rapp cooks meals on his flatbed truck outside the River Tavern. Photo by Caryn B. Davis


Chester remains a not-so-secret destination among gastronomes. The River Tavern, known for its popular “Dinners on the Farm” fundraisers, occupies a contemporary space fit for yoga classes. Polished-wood floors, a teak-and-zinc bar set off by bright red stools and atmospheric black-and-white seascapes on the walls set the stage for tantalizing, fresh-from-the-farm cuisine. The Wheatmarket specializes in picnic lunches, specialty soft drinks (among them Swedish Kristall Pear Soda and Virgil’s Rootbeer), fine cheeses, crackers, chips, oils, jams and other upscale delights. Then there’s Restaurant L&E, which has replaced the Restaurant du Village on Main Street and serves fine French cuisine using local ingredients whenever possible.

Scenic Selden Creek, on the east bank of the Connecticut River, winds behind Selden Neck Island. Photo by Caryn B. Davis


If you’re looking for nightlife, head for the Pattaconk, a popular local bar where the outside patio generally rocks until 2:00 a.m.

On the quieter, natural side, this stretch of the Connecticut River is a great place to explore in a small boat or kayak. You can follow Chester Creek all the way up to Carini Nature Preserve, with a stop at Moravela Restaurant’s dinghy dock for a pizza on the way.

Chester’s Main Street is home to numerous galleries and boutiques. Photo by Caryn B. Davis


Selden Creek, which flows behind Selden Island, directly across the river from Chester, is a popular detour off the main river. Here, sycamores, oaks, cedars, wild rice and cattail reeds lined the narrow ribbon of water (4 to 11 feet MLW), with beaver, muskrat, blue heron and coyotes going about their business among the vegetation. Selden Island State Park is only accessible to boaters, and offers hiking trails and even campsites (reservations required). It’s a great spot for a picnic and a swim.

Another interesting paddling spot is Hadlyme Creek, just north of Selden Creek, which winds deep into vast marshes teeming with birdlife.

For boaters launching in Chester, there are plenty of interesting downriver places to visit, including Essex, Old Lyme and Old Saybrook. And of course, Long Island Sound is just 10 miles south.

Hays Haven Marina has a fuel dock, a ship’s store and a launch ramp. Photo by Caryn B. Davis
A pooch-toting customer examines the fine dishware on display at Ceramica. Photo by Caryn B. Davis
A family of swans paddles along Selden Creek. Photo by Caryn B. Davis
Impressionist painter Leif Nilsson is one of many artists who make their home in Chester. Photo by Caryn B. Davis
Miss Jesse heads down Selden Creek toward the main river on a summer day. Photo by Caryn B. Davis


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