Gramercy–Flatiron to Upper East Side
Start station: Broadway at 24th St
End station: Central Park South at Sixth Ave
Don’t waste an hour queuing up at Madison Square Park’s Shake Shack when, in the same amount of time, you can book it from there to Central Park and have a nice picnic. How, you ask? Stock your bike-friendly bag with gourmet goods at Mario Batali’s Eataly (200 Fifth Ave at 23rd St; 212-229-2560, eataly.com), such as Agricole Del Sole bruschette ($2.20), a jar of Roi basil pesto ($8.80) and Geraci green olives in brine ($8.80). After nabbing your ride, breeze up Sixth Avenue and mutter awww while passing the beautiful tourist traps you take for granted (Bryant Park, the Empire State Building et al.). Once docked, scope out a grassy area near The Pond (Central Park, east side between 59th and 63rd Sts; centralparknyc.org) and toast to your pastoral lunch, the summer season and not having to wait the length of a movie for a burger.
Midtown to Chelsea
Start station: 59th St at Eleventh Ave
End station: 16th St at Tenth Ave
News flash: Getting around midtown in any mode of transportation can be a bummer. That’s why we dig cruising through the area via the Hudson River Greenway, which offers a relative sense of serenity along the waterway’s coastline. Watch for the Intrepid Sea, Air & Space Museum (Twelfth Ave at 46th St; 212-245-0072, intrepidmuseum.org), as well as the cruise ships leaving Pier 83 (Twelfth Ave at 42nd St). Then get back to nature by taking a pit stop at Chelsea Waterside Park (Twelfth Ave at 23rd St, hudsonriverpark.org), which boasts wonderful river views—not to mention adorable pups scurrying around its dog run. After dropping off your bike, chill out with a small scoop ($4.50) at the Van Leeuwen Ice Cream Truck (Eleventh Ave at 15th St, vanleeuwenicecream.com) mere blocks away.
Williamsburg to Fort Greene, Brooklyn
Start station: Metropolitan Ave at Bedford Ave
End station: Clermont Ave at Lafayette Ave
The Brooklyn Waterfront Greenway—a still-developing path connecting the borough’s waterfront—also merits a ride, serving as a de facto tour of BK’s industrial and multicultural history. First, rev up with some fine caffeine from the long-standing Oslo Coffee Roasters (133B Roebling St between North 4th and 5th Sts; 718-782-0332, oslocoffee.com). Once energized, grab your wheels and explore the Greenway’s first leg via Kent and then Flushing Avenues, where you’ll coast by the ever-changing Brooklyn Navy Yard before cutting over into your destination by way of Clermont Avenue. The dock is just outside Saturday’s Brooklyn Flea (176 Lafayette Ave between Clermont and Vanderbilt Aves; 718-928-6603, brooklynflea.com), so you can treat yourself to a postpedal spending spree on vintage and indie wares, artisanal eats and other goodies.
Start station: Ave B at 2nd St
End station: First Ave at 3rd St
Kick off this laid-back Alphabet City loop by heading up Avenue A and swinging by venerable crate-digger haven A-1 Records (439 E 6th St at Ave A, 212-473-2870)—which has survived the nabe’s changing tides of retail since 1996—and sifting through its dollar selections on the sidewalk out front. Then detour through underground-culture landmark Tompkins Square Park (Ave A to Ave B between 7th and 10th Sts; 212-274-1111, nycgovparks.org)—by walking; don’t be that dick who acts like it’s not a big deal to fly through a walkway—over to Avenue B. After that, head downtown, hook a right at 3rd Street, and drop off your two-wheeler. Now it’s time for a much-needed beer. Luckily for you, d.b.a. (41 First Ave between 2nd and 3rd Sts; 212-475-5097, drinkgoodstuff.com), a craft-brew bastion with an airy, season-appropriate backyard, is a stone’s throw away.