Sailboats swing on their moorings in Black Rock Harbor. Photo/Caryn B. Davis

Many boaters think of Bridgeport as an industrial seaport fallen on hard times. However, the city has seen many changes in recent years—most for the better—and now has much to offer the aquatic visitor who plies the waters of Long Island Sound.

Bridgeport owes much to P. T. Barnum, who based his famous circus here in the late 1800s, and visitors can still feel his impact on the city. The man who gave us the “Greatest Show on Earth” was also Bridgeport’s most illustrious mayor (he served in 1875 for a year). Downtown, the Barnum Museum brings circus freaks and school groups together to peruse exhibits about this master of promotion and his legacy.

The 2.5-mile-long Seaside Park, covered with sunbathers during the summer, was a gift from Barnum to the city. It was designed by Frederick Law Olmstead, the man who gave us New York City’s Central Park. A few miles from the waterfront, Beardsley Zoo is purported to house a few descendants of Barnum’s original menagerie. The showman was known to exercise his exotic animals on the city’s leafy boulevards.

Bridgeport Harbor still bears a decidedly industrial look. The harbormaster’s dock is adjacent to the high-speed-ferry terminal, where crowds gather for the 90-minute ride to Port Jefferson. Directly behind the terminal is the gleaming Total Mortgage Arena, a local venue for events and performances. The ferry and arena draw most Bridgeport visitors, but there’s much more to appreciate here, particularly if you’re a boater.

The Soldiers and Sailors Monument at Seaside Park. Photo/jllm06 at Wikimedia

The largest boating facility in Bridgeport is Bridgeport Boatworks on Cooks Point inside the harbor. It specializes in servicing large yachts and commercial vessels, and boasts no fewer than three Travelifts, including one capable of hauling 700 tons. It also features a fuel dock, but does not offer transient accommodations.

Traveling east, you’ll encounter Johnsons Creek, a well-protected waterway where a field of petroleum tanks faces the Miamoque and East End yacht clubs. Both offer reciprocity to members of affiliated yacht clubs.

Opposite the mouth of Johnsons Creek sits a scruffy barrier island called Pleasure Beach, the western tip of which is owned by Bridgeport (the rest is part of Stratford). Once home to a summer resort colony and an amusement park, the island is open to the public during the summer. A water taxi provides transportation to and from the beach. The sprawling marshes behind the barrier beach, part of the Stewart B. McKinney National Wildlife Area, invite exploration in a kayak or paddleboard via Lewis Gut.

Back on the western side of Bridgeport Harbor, a coal-fired power plant occupies a significant portion of the shoreline, although the owners are in the process of retiring the plant. Just west of the plant is Seaside Park. The 325-acre park and beach extend from the mouth of the harbor to the mouth of Black Rock Harbor at its western end, where a former garbage dump, “Landfill Hill,” now covered with trees and shrubs, serves as a windbreak for a protected cove.

From the top of Landfill Hill, the picturesque view of Black Rock Harbor may catch you off guard. The Black Rock Harbor mooring field, which contains boats of every stripe, lies between the park’s foliage-rich promontory and the tony shorefront neighborhood of Black Rock.

At the head of the harbor is Captain’s Cove Seaport, home to a full-service marina, as well as colony of shops, museums, and restaurants, all decorated in colorful Caribbean pastels. The Cove Restaurant, which according to one aficionado has the “best fish and chips this side of London,” sports a second-floor bar shaped like a tugboat and a huge model of the Titanic suspended from the ceiling.

Adjacent to the Seaport is the smaller Cedar Marina, which offers transient accommodations and service. Reservations can be made online.