See the Golden Gate Bridge from the best vantage point -- your bike.
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Ernest Hemingway would love modern Portland. Or Boulder. Or Austin.

No, not because of all the great local beer. Though surely he would have guzzled his fill of that.

What the cranky author really would love about these cities is the biking.

“It is by riding a bicycle that you learn the contours of a country best, since you have to sweat up the hills and coast down them,” Hemingway wrote. “Thus you remember them as they actually are.”

We asked nationally recognized bike advocates across the United States, and reviewed information from the League of American Bicyclists, Alliance for Biking & Walking and the U.S. Department of Commerce to determine the best U.S. cities to discover by bike.

Portland, Oregon

Cycling is a way of life in Portland.

“The groundwork for the city’s bike infrastructure was laid over 20 years ago,” says Brian Zeck, bike manager of Portland’s River City Bicycles. “It has built upon itself over the years and bicycling has become somewhat ingrained in the culture of the city.

“In some ways, Portland now has the feel of a European city.”

That infrastructure includes 106 kilometers of bike paths, 48 kilometers of low-traffic bike boulevards and 283 kilometers of bike lanes, all of which are used with gusto by the 8% of citizens who claim that biking is their primary form of transportation, and 10% who say a bike is their secondary vehicle.

In 2008, the League of American Bicyclists named Portland its first platinum-level Bike Friendly Community. The recognition was the result of groundbreaking efforts like the Create-a-Commuter program, which provides bikes, equipment and safety lessons for low-income locals.

The League of American Bicyclists also took into account the estimated 2,100 races, rides and other biking events held in Portland each year.

Minneapolis, Minnesota

Minneapolis' Nice Ride Minnesota system is a seasonally operated bike-share system.

“Bicycling” magazine incited outrage in the biking community in 2010 when it announced that Minneapolis beat out Portland as its most bike-friendly city in the U.S.

The distinction is especially impressive when one considers how non-bike-friendly Minnesota winters can be.

Regardless, Minneapolis still has the second-most bike commuters of all big cities. Locals say that’s because what the city lacks in ideal weather, it makes up for in ideal topography.

“It’s super flat here, there aren’t a lot of hills and I think that’s really where it all started,” says Stephen Cottrell, sales manager at Freewheel Bike in Minneapolis. “It was just a matter of time before the bike infrastructure was built.”

“The city council is making the investment in infrastructure and making the effort to make sure roads are not exclusive. They want everyone to realize that, whether it’s a Minnesotan in a car or a Minnesotan on a bicycle, we’re all just a Minnesotan using the road.”

Boulder, Colorado

Cycle with a glorious view like this one, of the Boulder Reservoir.

You can go almost anywhere in Boulder on a bike. At least 95% of city streets are open to cyclists.

That comes to about 600 kilometers of unofficial bike routes.

On top of that, the city has invested heavily in recreational cycling – most notably with Valmont Bicycle Park, a 182,000-square-meter chunk of land filled with trails, racecourses and dirt jumps.

“There’s a very large bicycle culture, so you don’t feel like the outcast when you’re commuting or riding for fitness,” says Paolo Durocher of Boulder’s University Bicycles. “The altitude attracts a lot of professionals for training purposes, so you get that runoff as far as the culture, the innovation and the overall support.”

Madison, Wisconsin

Not even consistently snowy winters put off cyclists in Madison, Wisconsin.

Madison gets bike-friendly points for being filled with dedicated cyclists.

“It’s really not all that much fun to be outside when there’s snow and ice on the ground, but people still ride,” says Ben Scherer, sales manager at Machinery Row Bicycles. “And they do it because the people here genuinely love to ride bikes.”

The city itself also scores for forming the Platinum Biking City Planning Committee, an outfit devoted to raising Madison’s rank in the League of American Bicyclists’ annual list.

Their efforts have paid off. In peak season, the city recorded around 11,000 bicycle trips through downtown per day.

“The community on a whole is really receptive,” says Scherer. “The city has a separate crew of street workers that make sure that the bike lanes and paths are clear of snow and debris and easy to use. Everywhere in the city there are free bike route maps.”

MORE: Great-grandmother cycles 10,000 miles – and she’s not stopping

San Francisco

Bicyclists ride by an automated real-time bike counter in San Francisco, California.

“It’s a city that allows you to be a hip, cool 20-something and ride your bike as your prime use of transportation, and nobody cares,” says Chris Lane, owner of Roaring Mouse Cycles, in the city that would put Hemingway’s appreciation for straining up hills to the test. “You can be a hipster on a fixie or you can be a category-one racer on your six-kilo road bike.”

Much of the bike friendliness comes from outstanding efforts by the local government. Police put major emphasis on bicycle safety, collision reports and theft prevention.

San Francisco has focused on bike-friendly policy since 1973, and has the highest percentage of bicycle commuters out of all cities with a population of more than 500,000.

The City by the Bay plans on staying ahead of the curve with the goal of encouraging 20% of all city trips in 2020 to be made by bike.

Austin, Texas

Austin, Texas is a famously bike-friendly city.

“We don’t have the kinds of numbers that Minneapolis or Portland have when it comes to daily commuters on bicycles, but I think we make up for it with weather and attitude,” says Craig Staley, general manager at Austin’s Mellow Johnny’s Bike Shop. “You can ride all year round. In the middle of summer it’s 24 C and sunny.

“The city is really changing its mindset and focusing on bicycles. If they’re re-striping or paving a new street, bike lanes are in the discussion right off the bat every single time.”

Austin’s commitment to cyclists doesn’t stop there. The city has reduced auto lanes to accommodate more bike lanes.


The best way to explore the Windy City is by bike.

“There are just a whole lot of bike lanes,” says Adam Kaplan, head bike fit technician at Get a Grip Cycles in Chicago, a town that admittedly represents the start of a bike-friendly drop-off on the list.

Inclement weather for half the year and large distances to traverse don’t exactly encourage biking.

Still Chicago has 188 kilometers of on-street bike lanes and more than 48 kilometers of shared lanes. Overall, the city’s bikeway network covers about 560 kilometers.

“Even though there’s a high volume of traffic, having that three feet of real estate pretty much everywhere you go is very helpful,” says Kaplan. “A lot of businesses have incentives for their employees to bike to work. The outgoing and incoming mayors have both been very bike-friendly in that they have created legislation, allocating funds for different modes of transportation.”

The city even has Bicycling Ambassadors, dedicated to teaching drivers to interact with bikers.

MORE: The case for bicycles’ inevitable triumph over cars

Washington, D.C.

Finally catching up with other U.S. cities?

The nation’s capital is finally taking a leading role in promoting healthy, eco-friendly commuting by launching the largest bike-sharing system in the country.

Capital Bikeshare provides more than 1,200 bicycles dispersed over 140 stations around the city and Arlington, Va.

However, many locals admit they still don’t feel a strong sense of cycling community.

“There is not one unified bike culture here,” says Walker Wilkerson, mechanic at The Bike Rack. “You don’t just have a bunch of roadies. You don’t just have a bunch of fixie kids. It’s not just mountain bikers.”

“You’ve got the amateur road racer and you’ve got grandma and you’ve got Joe Six -Pack, all trying to get to work and all riding in the same bike lanes on the same street. It’s not as much a bike city as it is a city where bikes are a very viable form of transportation.”

Jennings Brown has worked as an editor and writer for magazines including Popular Mechanics.

Editor’s note: This article was previously published in 2013. It was reformatted, updated and republished in 2017.