Central Park
1. Start at Columbus Circle (Central Park South at Central Park West), where the cycle-deficient can rent wheels at Bike and Roll (bikenewyorkcity; 2hrs $28, 4hrs $39, day $44; includes helmet). Unless you plan on stopping, it won’t take more than an hour to complete the loop.
2. Your first destination should inspire. Dismount when you reach the one-way Center Drive and walk south to Artists’ Gate Plaza to see statues of Latin American icons José de San Martín and José Julián Marti riding dramatic, rearing horses. Take a page from their book: Hop back in the saddle, pop a wheelie and ride back up Center Drive.
3. Between 77th and 78th Streets, keep an eye out on your left for Still Hunt, a sculpture by Edward Kemeys of a crouching panther perched on a rocky outcrop. Now is the time to scream “Duck! Panther attack!” at your unsuspecting companion.
4. As you make your way north on East Drive, you’ll find Cleopatra’s Needle, an Egyptian obelisk dating to 1500 B.C., rearing up on your left. A little farther along, you’ll pass a larger-than-life granite statue of founding father Alexander Hamilton.
5. Once the Metropolitan Museum of Art is behind you, keep your eyes peeled for Frank Lloyd Wright’s architectural masterpiece the Guggenheim Museum on your right.
6. After a long, flat stretch, you’ll swoop down a slope bearing left. If you’re making a day of it, put on the brakes, tie up your steed and have a refreshing dip in Lasker Pool. (Remember to bring your own lock for the pool lockers.) Otherwise, continue down the hill and take a break by Harlem Meer. You’ll need it: The next leg of your journey is the longest, steepest hill in the loop.
7. Once you begin to approach Strawberry Fields, look to the right to see the twin towers of the San Remo apartment block looming above.
8. Before you return to Columbus Circle, cut across the two-way Terrace Drive and follow the music to the Central Park Skate Circle (Sat, Sun 2:45–6:45pm) on your right, then roll farther along to bask in a fantastic elevated view of Bethesda Fountain against a backdrop of boaters on the lake.
9. To finish the ride, we recommend continuing to where Center Drive meets East Drive and turning right (south) to Doris C. Freedman Plaza. Grab a Belgian-style waffle or ice cream from the Wafel and Dinges truck and take in the Public Art Fund’s installation of Paola Rivi’s rotating plane How I Roll.