Built in 1823, Fayerweather Island Light marks the entrance to Black Rock Harbor. Photo by 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 boaters. Bridgeport is located 50 miles from New York City and 11 miles from Port Jefferson, on Long Island. It can be described as “exciting,” “epicurean,” “historic” and “quirky”. The “quirky” part owes much to P. T. Barnum, who based his famous circus here, 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 city.

The 2 1/2-mile-long Seaside Park, covered with sunbathers during the summer, was a gift from Barnum to the City of Bridgeport. It was designed by Frederick Law Olmstead, the man who shaped 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. He 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 landing, where crowds gather for the 90-minute ride across the Sound to Port Jefferson. Directly behind that (and sharing a parking lot) is the ballpark that was custom built for the local farm team, the Bridgeport Bluefish, and the gleaming Arena at Harbor Yard, a local venue for big-name performers. The ferry, ballpark and arena draw most of the visitors to Bridgeport, but there is much more to appreciate here, particularly if you’re a boater.

Across from the ferry dock, the imposing Derecktor Shipyard builds and repairs massive ships. Opened in 2001, Derecktor’s has built some of the world’s best-known high-speed ferries, tugs and fireboats, as well as the longest catamaran (145 feet) ever manufactured.

Next to Derecktor’s lies the vacant remains of the Turbana Corporation, through which all bananas coming into the Northeast used to funnel. The land, which is for sale, is now owned by a group of longshoremen and best suited for an apocalyptic movie set. Abutting this property is the cute, solitary Dolphin’s Cove Restaurant and Marina. Owned by Teresa Pinheiro, Jack Matias and their three grown sons, Dolphin’s Cove flies the flags of 30 nations, representing a diverse clientele, many of whom make their way across Long Island Sound by boat to dock and dine here.

Read the story Bridgeport Fishing Information


Traveling east you’ll encounter Johnsons Creek, a well-protected inlet where a field of petroleum tanks faces the Miamoque and East End Yacht Clubs. This is where most recreational boaters who hail from Bridgeport Harbor keep their boats.

Just outside Johnsons Creek sits a scruffy little island called Pleasure Beach, which is owned by the town of Stratford. Once home to a summer resort colony and an amusement park, the island is now closed to the public. Shells of summer cottages, bathing pavilions and a gazebo that never opened share the terrain with overgrown vegetation. Several of the abandoned houses have been burned by arsonists. Because endangered piping plovers nest here, plans are afoot to sell the property to the Fish and Wildlife Commission, although nothing has been finalized. Recently, a temporary road was built down the stretch of beach to the cottages so that debris could be removed from the island. For now, boaters are not allowed access to this unresolved patch of land languishing in the shadows of the venerable coal-fired powerplant, United Illuminating.

The plant occupies a significant wedge of the western bank of Bridgeport Harbor, with its own lighthouse (for sale) and bustling coal-offloading docks. West of the plant is the 2 1/2-mile Seaside Park, a 325-acre gift from P. T. Barnum to the city he loved. Several Victorian-era bathhouses and pavilions are still in use, but only a few have been rehabbed and most inexplicably remain closed. The park extends from the mouth of Bridgeport 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, acts as a windbreak for a scenic cove.

After gazing upon 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 a foliage-rich promontory and a tony shorefront neighborhood. At the head of the harbor is the Captain’s Cove Seaport, home to a full-service marina, as well as shops, museums and restaurants, all decorated in Caribbean hues. The Cove Restaurant, which according to one aficionado has the “best fish and chips this side of London,” sports a second-floor bar built like a tugboat and beside it, a huge model of the Titanic suspended from the ceiling. With a couple of small museums, a harbor cruise boat, a charter-fishing boat and a full-service marina, it would be tempting to stay put here for a weekend. But then you’d be missing out on Bridgeport’s many other marvels, both ashore and on the water.

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