A Guide to Off-Season Stonington

Stonington Borough is a charming oddity in a few ways. It represents one of those bits of local trivia that can make all but the most devoted Connecticut nerd’s eyes glaze over. As Connecticut’s oldest borough (incorporated in 1801) the little village is located within the town of Stonington yet is distinct from it; its governing body is the Board of Warden and Burgesses. Its geography, too, sets it apart: as a peninsula, a mile long and a few blocks wide, Stonington is a tiny place looking out on a great ocean. It is fitting that it boldly faced down a naval force far larger than its own, and that it has produced generations of fishermen, sea captains, and explorers.

Another strange thing about Stonington is that it’s somehow managed to fly almost under the tourism radar. As picturesque as any other historic New England fishing village – some say more so – it has generated just a fraction of their hype as a destination.

That is now changing, slightly, as more and more travelers pick up on what residents of the Connecticut shoreline have understood for ages. But you’d never know it when the weather cools. Visit Stonington in the fall or winter and you won’t find any tourists; you won’t see many people at all, in fact, aside from carpenters making repairs to summer homes and a few locals heading to the library or ducking into Tom’s News and General Store. Some Stonington attractions close up for the colder months, but that doesn’t mean it’s not worth traveling to this tiny borough in the fall. In fact, it’s almost more pleasant when the summer crowds – such as they are – have gone, and the streets are yours to explore.

Where to Walk

Stonington is gloriously walkable, and you can’t go wrong if you simply set out on foot and wander. But it’s also nice to take yourself on a mini walking tour to ensure you don’t miss anything. 

Park in the lot on Church Street, then walk down Water Street to Stonington Point. From there, walk back up Water Street until you reach Cannon Square. Turn right, then left onto Main Street. Continue on Main until you reach High Street, then turn left (the Stonington Free Library and Wadawanuck Square will be on your right.) Follow High Street down to the Town Dock, then from there, walk back on Pearl Street to Water Street. Turn right to follow Water Street back to the Church Street parking lot. Water and Main are the Borough’s main drags, where you’ll find most of the shops and restaurants as well as most of the notable sights. But all along the way you’ll be tempted to investigate the short, residential side streets. Stonington’s homes, with their subtle nautical details, historic plaques, and colorful front doors, account for at least half the charm of this little town.

Sights to See 

As you walk, there are a few highlights you might want to look out for. The Town Dock (1 High Street), home of Connecticut’s last commercial fishing fleet, is thoroughly unpretentious; where another town in another state would have created a photo-ready showpiece, here there is simply a small working waterfront going about its day as seagulls swoop overhead. The Old Lighthouse Museum (7 Water Street) is open seasonally, but the lighthouse itself is a must-see, a pretty yet sturdy stone house built in 1840 to warn ships of the dangers of Fishers Island Sound. The titular guns of Cannon Square (10 South Main Street) were used by locals to repel a British attack during the War of 1812; they stand beside an obelisk commemorating the event now known as the Battle of Stonington . (Roadside markers in the borough also refer to this defining moment in local history.) More of Stonington’s history can be seen in the presence of two 19th century buildings on Main Street: the Portuguese Holy Ghost Society (26 Main Street), which still hosts meetings and events, and the granite former Custom House building (21 Main Street), a reminder of Stonington’s trading days. Other sites are less obvious: a humble plaque near the United Church of Stonington (67 Main Street) commemorates Connecticut’s first railroad. The James Merrill House (107 Water Street) is a literary landmark masquerading as just another storefront. 

Selected Shopping 

If you’re looking for a shopping experience you won’t find in all those other adorable little seaside towns, don’t miss the Velvet Mill (22 Bayview Avenue.) Formerly the American Velvet Company factory, this hulking brick building has been converted to a home for a variety of small shops, businesses, and artist studios. In the off-season, the Stonington Farmers’ Market moves from the town docks to the shelter of the Velvet Mill; it’s open Saturdays from 10:00 a.m. to 1:00 p.m. 

Many of Stonington’s shops are located on Water Street. An unexpected find here is jewelry store A.K. Dasher (141 Water Street), a surprisingly affordable source for good quality pieces in sterling silver and a variety of gemstones.

A short distance from the center of the borough, the eclectic Fun Company Sample Outlet (71 Cutler Street) sells clothes, bags, and a wide assortment of candles, gifts, toys, and luxurious (but discounted) linens. 

Pockets of Nature 

Part of what gives Stonington its old-fashioned appeal is its compactness – the houses line up next to one another and the sidewalks are just steps from the front doors. But the Borough never feels too densely packed. It’s waterfront and its preserved open spaces ensure that nature is always close at hand. 

The easiest place to see this is at Stonington Point and the adjacent DuBois Beach (end of Water Street.) The beach is simple, tiny, and peacefully deserted in the off-season. The Point is essentially a parking lot with a large American flag flying above it, but that description does not convey the special atmosphere of this spot. Standing here, you feel a little like you’re poised at the edge of the world, and you can see why Stonington boasts of being the only town in Connecticut to face the Atlantic Ocean.

Off of Main Street, Dodge Paddock/Beal Preserve (Wall Street) provides a different sort of coastal view. A small but wild-feeling place where rocky shore meets meadow, it’s managed by Avalonia Land Conservancy, which oversees many of the preserved open spaces in the area.

Another secret waterfront stroll is hiding behind the Stonington Commons condo complex on Water Street. (Behind the private parking lot opposite Cannon Square.) This little walkway begins at the gazebo and winds past docks and beach grasses to the concrete seawall, a reminder of the precarious reality of this seemingly idyllic place.

Food & Drink

For a hot beverage and a baked treat in an impeccably Instagrammable setting, stop at Social Coffee Roastery (117 Water Street.) A cozier, more relaxed option is Indulge (17 High Street), which has coffee and tea as well as a fuller breakfast and lunch menu. 

For a tasty lunch or dinner in a casual waterfront setting, with plenty of seafood dishes and many other choices too, try Dog Watch (194 Water Street) at Dodson’s Boatyard. 

Arguably the most beautiful spot in Stonington to enjoy a glass of wine is Saltwater Farm Vineyard (349 Elm Street), which is open through December. For a cozier, wine-by-the-fireside vibe, Stonington Vineyards (523 Taugwonk Road) is open year-round. 

More dining options can be found at the Velvet Mill (see Shopping, above.)

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