The Best Cycling Cities in America

Pros: The scenery, being a messenger here will prepare you for anything.
Cons: The hills, the roads, the wind.

San Francisco seems like the kind of city that would be good for just one kind of cyclist-the ones with a death wish. Anyone who's seen a Dirty Harry movie knows what those hills are like, and it's not just going up them that could prove problematic. That said, bike messengers use the city as a proving ground, and the city has done much in the past four years to become more bicycle friendly. There's still a lot of work to do, but the ride across the Golden Gate Bridge into Marin alone is worth the trip. Also worth noting, the first Critical Mass ride was held in San Francisco in 1992.

Pros: Home to many cycling pros, all levels of cycling.
Cons: High altitude, good luck keeping up on the local training ride.

Boulder is where the pros live and train, thanks to the high-altitude setting and laid-back atmosphere. It's also home to the Morgul-Bismark loop, which featured in American Flyers, as well as the Coors International Cycling Classic. Colorado played a large role in the early days of both American road racing and the birth of mountain biking, so it should come as no surprise that cycling remains a priority today.

Pros: So bike friendly it's almost scary, home to many custom bike builders.
Cons: Chicago-style winters, a lot of Treks.

In a sense, Madison is the cycling Detroit, only without the bankruptcy. There are plenty of custom framebuilders that make their home in or around Madison (including Waterford and Ellis Cycles), and slightly larger bike company Trek is actually based in Madison itself. What this means is two things: 1) Plenty of bike advocacy, and 2) This is where you want to be if you're looking for a job in the industry, or just catch sight of prototypes before Interbike. And if you're just getting into cycling, they have a bike share setup AND a bike rest stop. Not to mention a dedicated website.

Pros: Tons of cycling heritage, fixed-gear heaven.
Cons: Lousy winters, sketchy neighborhoods.

There's something about the experience of cycling in an old Eastern city (Philly, New York, Boston) that simply can't be duplicated anywhere else-at least not in the U.S.. Philadelphia combines New York's urgent urban feel with more relaxing rides along the Schuylkill River. It was also home to the Philadelphia International Championship, a world-class, single-day race that started in 1985 and was a victim of budget cuts this year. Thriving BMX and fixed-gear scenes complete the picture.

Pros: Amazing coffee, a bike master plan.
Cons: Hills, rain, the Sonics moved.

If Portland is such a great cycling city, and it is, it only follows that Seattle (and Vancouver) would be great cycling cities, as well. Which they are. Seattle combines Portland's weather and San Francisco's hills (well, not quite) to make a spectacular Northwest mix. Seattle's Bicycle Master Plan stands out in the sense that Seattle even HAS a bicycle master plan. The fact that it calls for 450 miles of bike lanes is just icing on the cake. To see what exists already, download the official bicycling guide map here.

Pros: Central Park, Prospect Park, the views from the Brooklyn Bridge, bike share.
Cons: Bus drivers, tourists on the Brooklyn Bridge, overzealous cops writing tickets.

New York City is not a cycling city for the meek. Yes, the loops at Prospect Park and Central Park are relatively bucolic (as long as you ride them when cars are forbidden), but it's actually getting to them that's the tough part. Perhaps you could use some advice first. But for those brave enough to face the streets, there are miles of bike lanes and enjoyable rides along both rivers. When the city itself becomes too much, both Long Island and Westchester are only a bridge away. The new bike share program just allocates rides of 30 minutes or less, but the influx of more bikes should itself increase advocacy.

Pros: Varied terrain, excellent bike lanes.
Cons: Altitude, snow.

The latest NAHBS (North American Handmade Bicycle Show) was held in Denver in February, a fitting honor for a city that combines bike-friendly infrastructure with nearby mountains for off-road fun. And with everything from beginner courses to centuries offered on the BikeDenver site, every skill level is provided for. BYOO (bring your own oxygen).