No less a celebrity (and cyclist) than Mayor Richard M. Daley has challenged Chicago to be the most bike friendly city in North America, called "Bike 2015." The city already offers 315 miles of bikeways and leads the way with the McDonald's Cycle Center in Millennium Park, which includes showers, repairs, rentals, and even indoor parking. May's "Bike the Drive" is an annual car-free ride that ends with a giant party and concert. With Daley at the helm, Chicago's biking infrastructure is definitely off on the right (and left) pedal.

For more information: City of Chicago

The fact that hundreds of denizens in this northern clime insist on pedaling to work in the dead of winter earns the Twin Cities a mention. But the 5.7 Midtown Greenway, an urban inner loop for cyclists, receives legitimate kudos. The city also boasts 34 miles of street lanes, 56 miles of trails and a loop around just about every lake. A city plan will guarantee bike path access to all neighborhoods by 2020.

For more information: Minneapolis

The Big Apple has begun a huge initiative to make biking a priority, including a plan to encircle Manhattan with a greenway. April's Five Borough Bike Tour involved 30,000 (registered) riders and 42 miles of car-free cavorting. NYC is still the "leader" in bike theft, so bring a lock. New green bike lanes are adding visibility and, this being New York, controversy to the grid, so visitors shouldn't always expect courtesy from those behind the wheel. However, the NY-based Transportation Alternatives, the best pro-bike organization around, is working hard to change this attitude.

For more information: Bike New York

Hills notwithstanding, 40,000 residents bike to work daily in San Francisco. The City's small geographical area also makes bike tourism ideal, especially now that new maps identify routes with less than Lombard Street inclines. For the hardcore, these same hills also provide tremendous recreational cycling circuits. Plus, touring across Golden Gate Bridge is arguably the most scenic bike path in America, if not the world. Every serious bike tourist should attend one SF Critical Mass, a combination of cycling empowerment and good old San Francisco activism. If the hills do prove too steep, just hop on the BART, which now accommodates bikes.

For more information: San Francisco Bike

Sure it rains all the time, but downpours hardly deter the thousands of bike commuters who pour downtown everyday. And, truth be told, the Seattle climate is more drought than precipitation from July through September. Seattle is also finally getting light rail, and bike trails will lead to stations that will connect to the airport as well as the downtown core. Visitors can decide between the new 1.5-acre urban mountain bike park or the ever-expanding18-mile Burke-Gilman Trail, arguably the U.S.'s top urban rail-to-trail success story. The trail will eventually surround the 55-mile circumference of Lake Washington.

For more information: Seattle

The only North American city that can boast having more bikes than cars, Davis' 100-plus miles of paths are so comprehensive, the department of education actually eliminated school bus service. The new $7.5 million tunnel beneath I-80 means visitors can pedal from the UC Davis campus to Sacramento without encountering a single automobile. Clearly, with 17 percent of all travel of the two-wheel variety, a "Bike Talk" radio program and a perfect climate for biking, Davis remains a city worth visiting to experience a bike-centric community firsthand.

For more information: City of Davis

North America's most European city hosts the annual Bike Festival every June, boasting the most (35,000-plus) rider involvement in world. The festival stretches from Friday's Un Tour la Nuit, the costume party cum critical mass cycling event, to the Tour de l'Ile de Montréal, an exclusively two-wheel ride through car-free city streets. Two hundred miles of bike trails also make the island Canada's top cycling city. The city takes its top rank seriously, recently launching a $90 million (CDN) plan full of initiatives to equip all buses and taxis with bike racks, add hundreds of miles of paths and add five times the bike parking space. Most exciting, Montréal now offers Vélo Québec, the first Paris-style rental program of its kind in North America.

For more information: Vélo Québec

The city of 1.2 million is flat and sunny with 850 miles of trails and lanes that take riders from shore to canyons—what's not to love? In fact, San Diego tops most lists of best cycling cities of more than one million people and it may one day surpass Portland (think constant temperature between 50 and 80 degrees—and no rain) as the city has added 300 additional miles of trails in the last three years alone. The Bayshore Bikeway, which conveys pedalers along a 24-mile oceanfront corridor, may be North America's most sublime trail, though escaping to mountain trails is also a snap. Try to visit during August's Midnight Madness ride (the party starts at PM.), and also make sure to visit the downtown velodrome and Olympic Cycling Training Center.

For more information: San Diego

Visitors have long traveled to Boulder to soak in its health-oriented aesthetic, including the world's largest mountain biking culture. This high altitude city also offers bike lanes on 95 percent of its arterials, forming 350 miles of paths and lanes, including extensive drainage route paths that convey plenty of pedaling miles with minimal street crossings. The City of Boulder also takes its biking infrastructure seriously, committing 15 percent of its transportation budget to bikes. The University of Colorado campus ensures biking multitudes and thus, high bike awareness among car drivers.

For more information: Boulder Colorado

The first American city to receive a Platinum Bike Rating from the League of American Bicyclists, this metropolis of 500,000 remains by consensus #1 among North America's bike friendly cities. Portland is not resting on its two-wheeled laurels however, having recently initiated a Pilot "Green Box" program that directs cars away from bikers at busy intersections. Visitors will find 164 miles of bike lanes, 66 miles of bike paths, 30 miles of bike boulevards and great access to mountain bike trails.

For more information: Portland Online