Stepping Out on the Town

NORTH

Toronto, Ontario

Temperatures can dip below freezing as late as April, but you can walk in warmth thanks to PATH, a 17-mile underground maze of walkways and shopping centers that links downtown hotels, eateries, and attractions. Outside you'll find a pedestrian-friendly metropolis where—no joke—locals stop to assist tourists. So it's easy to walk the short distances between bordering areas such as downtown Chinatown and the vintage shops of Kensington Market. To learn more about the city, try a free private tour from the Toronto Greeter Program (416-338-2786). And don't miss the CN Tower: at 1,815 feet, it's one of the world's tallest buildings. Its 1,776-step stairway is usually closed (oh, darn), so hop on the glass-walled elevator and ride to the top. On clear days you can see for 100 miles (800-499-2514; seetorontonow.com).

SOUTH

Austin, Texas

With 300 days of sunshine a year and 70-ish average temps, this charming capital city is perfect for outdoor strolling. Planners designed Austin to be compact and easy to navigate. Today the capitol building anchors the downtown area, and Congress Avenue splits the town east and west, so you'll easily keep your bearings. And main attractions&mdsash;from the capitol and the Austin Museum of Art to iconic Waterloo Records and music venues—are in walking distance of one another. For a change of pace, head downtown to the southeast corner beneath the Congress Avenue bridge, where, from April to October, 1.5 million Mexican free-tailed bats (they're not too creepy, we promise) make their nightly exodus in search of food. Never fear: they're stalking skeeters, not humans (866-462-8784).

EAST

Boston, Massachusetts

When your slogan is "America's Walking City," making our list is a slam dunk. Buildings are close together, and you can walk the 1.8 miles from the cafés and pubs of the Italian North End to the art galleries and bistros of the South End in about 45 minutes. Boston's 2.5-mile Freedom Trail connects 16 historic locations, including Paul Revere's house, the Old North Church, the site of the Boston Massacre, and the area around the Old State House. And for a guided tour of the trail, try one of the National Park Service's free escorted walks. North and west of the trail, you'll find Beacon Hill's steeper streets, which feature iron handrails for folks on foot (888-733-2678).

WEST

Portland, Oregon

Walkers love Portland, even with its drizzly clime. Maybe it's because city blocks in this flat locale are half the standard length (200 versus 400 feet). Or maybe it's because a special building code requires every new facility or major renovation to add pedestrian—enticing attractions—retail space, a restaurant, or artwork—at street level. Basically, locals think you're nuts if you drive, especially downtown, where you'll find the Portland Art Museum and the Oregon Historical Society. And if you walk over to the nearby Pearl District, you'll find the world's largest independent bookstore. The more than one million titles at Powell's City of Books are spread over 68,000 square feet—which takes up an entire city block (800-962-3700).