View of Norwalk Harbor from the water. Photo by Caryn B. Davis

Located 50 miles from Manhattan, Norwalk is a hard-to-pin-down kind of city. Families come here for the great museums, gourmands can’t wait to try out the newest bistro on the block, and boaters wax lyrical about the numerous marinas, great local fishing and ready access to many Long Island Sound daytrip destinations.

Norwalk Chart

Then, of course, there are the Norwalk Islands, located just a mile outside the harbor and offering all sorts of boatworthy activities. These 23 mounds of boulders, gravel, sand, silt, clay and vegetation protect the harbor from high seas and inclement weather, and are one of the reasons Norwalk is so attractive to boaters.

Sat Map

The islands vary in size and ownership. The Norwalk Recreation and Parks Department manages Shea Island and smaller Grassy Island to the east. Both are stony, scruffy tracts of land—as removed from the mainland as the Statue of Liberty is from Manhattan. But for many locals the pebble-strewn beaches and brushy interior constitute paradise on earth. Seasonal camping is allowed on these islands by permit from the Norwalk Recreation and Parks Department.

Norwalk Harbor Chart

Copps and Betts Islands are privately owned, as is perhaps the most notorious chunk of rock—Tavern Island. In the 1920s, an infamous entertainer and bootlegger named Billy Rose lived on Tavern and reputedly used the island as a depot for rumrunners.

Chimon (Chimmons), Goose and Sheffield Islands are part of the Stewart B. McKinney National Wildlife Refuge. Boaters are allowed on Sheffield Island, but access to Chimon and Goose is prohibited. At 57 acres, Sheffield features a hiking trail and a lighthouse built in 1868 that’s now maintained by the Norwalk Seaport Association. Visitors can access the island via the public dock, which is also used by the Sheffield Island cruise boats. It can be a busy place on weekends, when numerous people come to picnic on the island.

Throughout the warmer months, there’s generally some kind of celebration going on in Norwalk.

Thanks to their close proximity to the mainland, the Norwalk Islands are very popular among kayakers, many of who launch from Calf Pasture Beach, on the eastern side of Norwalk Harbor. From there it’s a relatively short paddle to the islands. The South Western Regional Planning Agency—a state governmental agency active in the preservation and improvement of the quality of life, the environment and the economy in southwestern Connecticut—has prepared a laminated chart and guide denoting canoe and kayak trails around the Norwalk Islands. The agency also installed informational kiosks at area launch ramps.

Norm Bloom & Sons oyster boats. Photo by Caryn B. Davis

The islands are surrounded by extensive oyster beds, which are marked by spindly stakes. Boaters must take care not to anchor in these areas. Oystering once was to Norwalk what whaling was to New Bedford, Massachusetts. It identified the town and was one of its primary industries. Oyster farming declined in the mid-19th century, but has since been making a comeback.

A ferry heads toward the Norwalk Aquarium. Photo by Caryn B. Davis

The Norwalk Islands chain lies in the shadow of the Manresa Power Plant, which has been off-line for several years. The plant’s huge, baby-blue buildings and looming smokestack have long served as navigational landmarks for Long Island boaters, signaling the entrance to both Norwalk Harbor and the Norwalk River. As you enter the Norwalk River, you’ll see Calf Pasture Beach jutting out on the eastern side of the harbor. The 33-acre beach and park is a popular spot among beachgoers and a great launching point for kayakers and other small vessels.

The Norwalk River is roughly 23 nautical miles long, originating from swampland in Ridgefield, Connecticut. From the north the river courses under Interstate 95, the Metro North railroad bridge, past the Maritime Aquarium and under the Stroffolino Bridge—an active drawbridge that connects East Norwalk with South Norwalk—before flowing into Long Island Sound. This wider, lower portion of the river—from the bridge on down—is lined with marinas, yacht clubs, restaurants and shops. The west bank of the river near the bridges is part of the SoNo Historic District.

Throughout the warmer months, there’s generally some kind of celebration going on in Norwalk. Crowds converge for the annual the SoNo Arts Festival in August and the Norwalk in-water boat show and Norwalk Seaport Association Oyster Festival in September.

The Visitors Dock helps make Norwalk a boater-friendly city. Photo by Caryn B. Davis

Boaters can easily access South Norwalk via the Visitors Dock, which is free for stays of up to one hour. For longer stays, the fee is 75 cents/foot for daytime stays; $1.25 per foot for overnight. From the Visitors Dock it’s a short walk across the bridge to the center of the action in SoNo. Once ashore, you can start off at the Maritime Aquarium, a former 1860s ironworks factory that was renovated in the 1980s as a state-of-the-art marine educational center.

Behind the aquarium parking lot is the head of the Norwalk River Valley Multipurpose Trail—a 1.5-mile ribbon of land that runs north along the Norwalk River to Mathews Park and on into Norwalk Center. The city also reclaimed a former town dump—halfway between the aquarium and Mathews Park—and named the refreshed 17 acres of land Oyster Shell Park. A footbridge connects the park to the multipurpose trail, which features a riverfront esplanade and amphitheater on the half-mile tract between the aquarium and Mathews Park.

Mathews Park is home to the Stepping Stones Children’s Museum, built with a clever eye toward the ways children learn through play. An angular mini-lighthouse marks the museum’s entrance. Inside, kids can experiment with river currents or learn cause and effect by manipulating a “color-coaster.”

Visitors check out the seals at the Norwalk Aquarium. Photo by Caryn B. Davis

A couple more museums downtown warrant attention. One block up Washington Street from the aquarium is the SoNo Railroad Switch Tower Museum. Train historians worked hard to preserve “Signal Station 44,” rescuing it from years of decay. Around the corner on North Main Street is the neoclassic Norwalk Museum—a charmingly antiquated place where the city’s history is distilled down to several exhibits on two floors. One displays Raggedy Ann and Andy, created in 1920 by Norwalk native Johnny Gruelle. Another showcases the history of the Norwalk oyster industry told through old photographs.

Downtown features one retail store after another. The Small Boat Shop on South Water Street is the largest seller of kayaks, canoes and dinghies in the country. Across from Rex Marine on South Water Street, the Cigar Factory Outlet draws visitors from all over, and Lillian August Warehouse and Villa Ceramica sells discount clothing and home goods. Taste of Holland offers imported salty licorice and other specialty foods. And Company, Inc., Oddz and SoNo Kids peddle upscale apparel, while Beadworks and Come Out and Clay provide an outlet for those creative impulses.

Sheffield Island Light, in the Norwalk Islands. Photo by Caryn B. Davis

After shopping and museum hopping, you can satisfy your appetite at a variety of eateries. If you like hamburgers, try Donovan’s. For steamers, try SoNo Seaport Seafood Inc. For tapas, head to Barcelona Restaurant & Wine Bar. You can pick up a bento box at Kazu, a Japanese restaurant. With El Acapulco (Mexican), Pasta Nostra (Italian), Bistro Du Soleil (Spanish-Mediterranean), Habana Bar & Grill (Cuban), O’Neill’s Pub (Irish), and many more, any craving will be satisfied.

If you crave nightlife there are several clubs in town, each catering to a slightly different crowd. Ego Bar-Lounge features ethereal, hypnotic music while movies play on diaphanous sheeting. The Loft, a trendy “cigar bar” with leather couches and televisions broadcasting baseball games, has a front patio open to the street that packs them in. On warm nights, the party spills onto the street—practically canceling the need for clubs at all.