Island-Hopping in New York City

Exciting island adventures await beyond the concrete jungle 

Governors Island, photo by Ian Douglas/The Waterfront Alliance 

There’s an oft-repeated myth that, back in 1626, Dutch merchants bought the island of Manhattan from the Lenape Indians for the equivalent of US$24 and a handful of beads. While this may not be precisely true, the tale has elicited its fair share of jaw-drops from anyone who has considered buying property in New York City, where one single square foot of real estate now fetches more than US$1,000 (in Manhattan, at least). 

The city has expanded a great deal since that first purchase, but it’s never lost its taste for acquiring islands. Beyond the obvious ones—Staten and Long—there are between 36 and 42 separate islands within New York City’s limits. (The actual number depends on how small a rock you’re willing to call an island.) 

No matter how you count, NYC has lots of island adventures to offer for anyone wanting to venture beyond the glittering glass and concrete canyons of Manhattan. 

Randall's Island 

1848

Governors Ball, photo by Forest Woodward

Randall’s Island is the antidote to any urban jungle syndrome you might feel in Manhattan. Quite simply, it is Eden in the Big City. Bordered by waterways known as Hell Gate and Bronx Kill, and once best known for its orphanages, reform schools and asylums (now long gone), this island is so much more promising than it seems. It is now the site of more than 60 sports fields, driving ranges, tennis courts and Icahn Stadium, where Usain Bolt smashed the 100-metre dash record back in 2008. 

If you prefer music and cultural festivals, the island is also home to a massive event site that hosts some of the city’s premier concerts and events, including Governors Ball, the Frieze Art Fair and the Panorama Festival

To reach Randall’s Island, you’re going to want to be on foot, so take a bridge in from Manhattan, the Bronx or Queens. Once there, explore the miles of waterfront pathways and prepare to forget that you’re in one of the biggest cities in North America. We suggest you start with a free Wildflower Meadow Tour, or maybe take the free Little Hell Gate Salt Marsh Tour, where winged wildlife like snowy egrets, red-tailed hawks and even butterflies are all flourishing. 

And, while Randall’s isn’t necessarily a foodie destination—we recommend picnicking in the Zenlike peacefulness of the Rock Garden—there is an extensive Urban Farm on the island. (Hands off the produce, though; those veggies belong to the thousands of schoolkids who come through there every year to learn about gardening and to get their fingernails dirty.) There’s also a working apple orchard that grows Newtown Pippins, which were developed in Queens. And you thought Big Apple was just a nickname.

City Island 

1823

Photo by Aaron Zebrook, The New York Times Redux

City Island, a hot spot for sailboat racers and sport fishers, is a place where the maritime history is so ingrained, locals make distinctions between “clam diggers” (City Island natives) and “mussel suckers” (those audacious enough to have been born anyplace else.) 

Here, local shipbuilders built minesweepers and tugboats during both world wars; since then, the island has produced seven America’s Cup-winning vessels. This proud past is on display at the City Island Nautical Museum, where models of Prohibition-era rum-running boats have pride of place alongside more “above-board” craft.

Located in the Bronx, tiny City Island—it’s barely one square mile large—is easily accessible by public transit and has a quaint, New England fishing town feel. Stroll the main street (City Island Avenue) and then head to King or Minnieford avenues where you’ll find tree-lined neighbourhoods with well-preserved 19th-century Victorian architecture. Antique shops abound, and they’re joined by an eclectic bunch of artisans. Check out Starving Artist Cafe, which offers live music and handmade jewelry.

The ships and shops are great, but it’s the classic seafood that just may be City Island’s main draw. You won’t find fussy cuisine here, just roll-up-your-sleeves deliciousness as the island’s many restaurants compete to offer the best lobster rolls—and other seafood favourites—on the Eastern Seaboard. Try a movable feast with the Baked Clams Oreganato at the Lobster Box followed by Alaskan King crabs at Sammy’s Fish Box

Governors Island 

1825

Nolan Park, photo by Terese Loeb Kreuzer/Alamy

Governors Island is where New Yorkers let their hair down—it’s a 172-acre playground that hosts festivals, parks and multiple recreation opportunities. Accessible by ferry from Manhattan or Brooklyn, it’s closed in winter, though it more than compensates with wide-open festive summers. 

Back in the 17th century, the island was exclusively reserved for visiting British governors, but today’s visitors no longer require permission from the Queen. (She’s probably not big on kayaking, anyway, but you should be, especially since Downtown Boathouse offers free kayak rentals.) If you’re stuck on the royalty thing, check out The Governor’s House, a lovely Georgian brick building that’s on the National Register of Historic Places. History buffs should also visit Castle Williams, a circular sandstone fort built during the turbulence surrounding the War of 1812. The cannons are gone, but the four-storey fort remains, with impressive eight-foot-thick walls.

The heart and soul of Governors Island is its festival schedule, always changing and always fun. The Governors Club—a magical combination of beach, beer garden and music venue—is a rocking party scene. Yes, you’re barefoot in the sand, your beer has a lime in it and you’re still in New York City. Don’t let the cognitive dissonance blow your mind.

Roosevelt Island 

1827

Photo by Mario Burger

Roosevelt Island sits right in the middle of the East River. To get there, you swipe your MetroCard and board the Aerial Tram, which is pretty much the coolest commute vehicle imaginable. You know that feeling you get when you stand against the window of a high-rise and look down? Well riding the Aerial Tram is like that, except the high-rise is swaying and there are 100 New Yorkers around you acting like nothing unusual is going on.

Roosevelt Island is just two miles long and 800 feet wide. You can stroll the whole thing in a few hours, and the views back toward Manhattan are spectacular. The island has gems of its own, too, including the Gothic-revival lighthouse (built in 1872) and The Octagon, formerly the New York City Lunatic Asylum, but now refurbished with a stunning eight-sided rotunda. 

The highlight of this island is Franklin D. Roosevelt Four Freedoms Park, a tribute to the U.S. president for whom the island is named. There’s a massive bronze bust of the great man, as well as the stirring words of his “Four Freedoms” State of the Union speech etched in granite. A double row of trees frames the harbour, creating a peaceful atmosphere that inspires quiet reflection.

Getting there: WestJet flies to LaGuardia 48 times a week from Toronto, and to JFK once a day from Calgary.