Why City Island Should Be Your Next Day Trip

City Island is the Bronx, but nautical. It’s New York, but quiet. It’s an urban neighborhood connected to the mainland by a short bridge; of the city, but not in it. It looks like a tiny piece of Connecticut’s coast or Long Island’s east end broke loose and migrated, starry-eyed, toward the action of the big city. 

The island is about 1.5 miles long by 5 miles wide. You can stroll, at a leisurely pace, from one end to the other in half an hour. From City Island Avenue, the main street, you can walk to the end of any of the little cross streets in a few minutes. When you get there, you’ll see a yellow sign that says END. Beyond that, the water begins, and you remember you’re standing at the extreme western point of Long Island Sound.

City Island Avenue is lined with a mix of everyday businesses (gas stations, Dunkin Donuts) and historic, eclectic storefronts. There are numerous restaurants, many of them focused on seafood, big old waterfront places that get packed on summer weekends. There are also antique shops and other quirky small stores. 

Between the usual city things – MTA buses, Con Ed trucks, NYPD SUVs, barbed wire loops around random parking lots – there are boats: real boats in marinas, pictures of boats decorating fences, models of boats anywhere and everywhere. The public school has a boat-shaped planter, bursting with colorful flowers, stuck to its facade. On the residential streets, you’ll see architecture you’d expect in a coastal New England village: dark shingled houses, stately sea captain’s homes, tiny cottages, and bungalows with beachy accents.

City Island was once the private property of Thomas Pell, ancestor of Senator Claiborne Pell, whose name you might know from your college grant or that terrifying bridge to Newport. The island, along with the land that would become the Bronx and Westchester County, was part of 50,000 acres granted to Pell in 1654 by Chief Wampage of the Lenape Indians (sometimes called the Siwanoy.) City Island changed hands several times before finally becoming part of the Bronx in 1898, but no matter who claimed it, its watery location was always its destiny. It became a center for oyster farming in the 1830s and shipbuilding in the 1860s. Construction of various types of vessels, from minesweepers to racing yachts, continued here through the 1970s, and the area’s maritime history and unique flavor is very much present today.

What to Do and See:

City Island is an ideal destination when you want to see a lot without necessarily doing all that much. In other words, it makes for an extremely chill – or if you prefer, downright lazy – day trip.

The City Island Nautical Museum, housed in a former school building, provides a self-guided walking tour of historic highlights. The route takes you past old wooden churches; venerable institutions like the Harlem Yacht Club, founded in 1883; significant homes; and other sites of note, such as the 19th-century Pelham Cemetery, built on a hill overlooking the water.

The island is also full of cozy little places to sit and relax. There’s Bridge Park and the Catherine Scott Promenade at the northern end, and Belden Point – from which you can just make out the brick, Victorian-style Stepping Stones Light in the distance – at the south. In the center of the island there’s Hawkins Park, a typical New York pocket park with a local twist: cute statues of marine mammals. (Bonus: it’s right next to the most adorable candy-colored ice cream shop, Lickety Split.)

Which brings me to places to eat. I stopped at Clipper Coffee, a small and friendly coffee shop with indoor seating as well as sidewalk benches perfect for watching neighborhood life unfold. If I’d stayed longer, I probably would also have checked out the Black Whale or City Island Diner. And of course, most visitors go with the waterfront theme; Johnny’s Reef, Tony’s Pier, and City Island Lobster House look tempting for ambiance alone, even before you peruse their extensive menus.

Tips:

From Connecticut, the easiest way to reach City Island is by car. Street parking is free, and plentiful at less crowded times, like weekend mornings in the off-season. Parking lots are reserved for customers of the many restaurants in the neighborhood. The island is very walkable, so once you find a spot, you shouldn’t have to do any more driving.

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