Route: Pier 84 to City Island
Distance: 18 miles (29 km)
The popular Hudson River Park bike path, which runs along Manhattan's west side, offers 13 miles (21 km) of continuous city sights on one side and the Hudson River and New Jersey on the other — and is absolutely worth its own ride. But for a more off-the-tourist-track journey, take the bike path north from Manhattan into the Bronx. Start at Pier 84 at West 43rd Street (near the Intrepid Museum), where Bike and Roll offers $10 hourly rentals. From there, it's nothing but paved cycling paths — and fabulous people-watching — to the George Washington Bridge at 178th Street. Cross under the bridge into Inwood Hill Park, where the crowds thin and the vegetation thickens, and then cross the Harlem River into the Bronx for a mix of urban grit and lush parks. The path turns east through Bronx Park, along Pelham Parkway, and finally over a series of small bridges to City Island in Long Island Sound. (Click here for a very detailed route description.)
City Island is an oddity: a sleepy New England fishing village in the middle of the city, with antiques shops, a nautical museum, some Victorian mansions and a diverse bird population that includes monk parrots. Best of all, it has 30 restaurants at which to chow down after a day's ride. Locals (there are only 4,500) prefer Sammy's Fish Box, the Black Whale and a pub called the Snug. After dinner, it is a short ride to the No. 6 subway line, which heads back into Manhattan.