TRAVEL: 9 MILES FROM DOWNTOWN
Ride gnarly trails without leaving Manhattan. Last May, the Fort George Trails, in Highbridge Park, became the city's first sanctioned MTB trail system. Working with the city's mountain-bike association and the IMBA, the parks department transformed undeveloped land into three miles of trails, including two knotty, experts-only singletracks. The new area boasts enough obstacles and variety to satisfy even the most jaded city dweller. Best of all, unlike everything else in Manhattan, it won't cost you a dime (open daily until dusk; nycgovparks.org).
TRAVEL: 50 MILES
Treat yourself at star chef Michel Nischan's Dressing Room (dressingroomhomegrown.com), a timber-and-fieldstone-fireplace- enhanced, all-sustainable-all-the-time eatery on the grounds of the historic Westport (Connecticut) Country Playhouse. Then make it a weekend at the nearby Inn at National Hall, a 134-year-old former bank overlooking the calm waters of the Saugatuck River (doubles from $325; innatnationalhall.com).
TRAVEL: 88 MILES
Explore the Shawangunks (also known as the Gunks), where two new ridgeline trails add seven miles to what was already world-class hiking and climbing. The Lenape Ridge and Minisink trails pass crags and cliffs east of the Neversink River, taking in distant south-facing views of the Delaware River Valley below (nynjtc.org). Your crash pad is 15 minutes away at the Inn at Cliff Park. Built in the 1820s, it has large rooms and 500 acres of trail-lined grounds (doubles from $129; cliffparkinn.com).
TRAVEL: 118 MILES
Ride the waves of Long Island's break-blessed Montauk with Izzy Paskowitz. The California-based surfing champ will lead an all-day clinic on September 15 ($300; paskowitz.com). Or simply rent a board from downtown's Air and Speed Surf Shop (rentals from $35; 631-668-0356) and tackle the waves any weekend you like, using the funky East Deck Motel (from $110; eastdeckmotel.com), in Ditch Plains, as base camp.