Rolling Easy Or Fighting Inconvenience
Not every city wants you on two wheels. Some make it effortless, while others make it feel like a test of survival. Urban design and local attitudes shift drastically as you ride from place to place. This breakdown highlights where cycling thrives—and where it stalls—so you know what kind of ride to expect there. Let's start with the bike-friendly places.
1. Crested Butte, CO
Pedal through this mountain town and hit a trail system that dates back to 1976. Every July, costumed locals join the Pearl Pass Tour, a wild ride up rocky terrain. Ride at altitude, sure—but also at 9,000 feet, where endurance tests become real.
2. Palo Alto, CA
Bike racks outnumber parking spots in some blocks, and that's not an accident. This Silicon Valley hub rolled out its first bike boulevard in 2003, inviting cyclists to cut through neighborhoods with fewer stops. You'll find traffic diverters and bike-only pathways. Watch for Stanford students hauling groceries uphill.
3. Provincetown, MA
Rolling into summer here means weaving past sand dunes and drag queens. The Provincelands Bike Trail loops through Cape Cod National Seashore like a dream. Stay alert as coastal winds and sharp turns can sneak up fast, especially in peak July traffic.
4. Davis, CA
Bikes outnumber people in Davis—no joke. Since 1967, the city has built over 100 miles of lanes and tunnels. Roundabouts even have separate bike paths. Davis also flaunts the U.S.'s first official Bicycle Hall of Fame, located right off 3rd Street downtown.
Ken Lund from Reno, Nevada, USA on Wikimedia
5. Berkeley, CA
Zippered with bike boulevards, Berkeley lets you glide across town without dancing with traffic. Cyclists dominate the road in this politically charged city where activism meets asphalt. Need a tune-up? Dozens of DIY repair stations dot the area, especially near the Telegraph and the university zone.
6. Santa Monica, CA
Cruise past ocean views on the Marvin Braude Bike Trail, but don't stop there. Santa Monica blends sun and sustainability with its 500+ shared bikes and protected green lanes. The city's Climate Action Plan directly ties urban biking to emissions targets. Yes, policy backs every pedal.
7. Boulder, CO
Riding through Boulder feels like skimming a wellness brochure—mountains, fresh air, and zen-level bike paths. The city maintains more than 300 miles of bikeways, many separated from traffic. Try the Goose Creek Path if you're looking for a flat, scenic connection across town.
8. Arlington, VA
Situated just across the river from D.C., Arlington proves you don't need to live in a big city to ride like a local. The Custis Trail connects neighborhoods and jobs. It's also part of the larger Washington & Old Dominion Trail, stretching 45 miles west.
FaceMePLS from The Hague, The Netherlands on Wikimedia
9. Cambridge, MA
Cobblestones and chaos? Not here. Cambridge reclaims its streets with protected bike lanes, especially along Massachusetts Avenue. Harvard and MIT cyclists set the pace, but even newbies find a groove. In 2023, the city required every major street redesign to include dedicated bike infrastructure.
10. Minneapolis, MN
Snow doesn’t stop the locals. Minneapolis thrives on year-round cycling. With over 100 miles of bikeways, it’s got winter maintenance that puts other cities to shame. The Midtown Greenway alone supports over 1.5 million riders a year—many commuting, even in single-digit temps, by studded tire.
Minneapolis Public Works TPP on Wikimedia
Sadly, not every city makes room for riders. Some barely notice you exist. So, it’s time to talk about the places where biking feels more like a dare than a daily routine.
1. Los Angeles, CA
Concrete dominates. With over 500 square miles to cover, L.A. barely scratches the surface of safe cycling infrastructure. Dodging traffic near Sunset or Wilshire is a nightmare fuel. Even painted lanes often vanish mid-block. In 2022, over 1,000 cyclists were injured.
InSapphoWeTrust from Los Angeles, California, USA on Wikimedia
2. Phoenix, AZ
Heat and hazard team up in Phoenix. Cyclists face wide and fast roads, and the city is ranked among the top ten for fatal crashes. Who's biking in 110°F weather, anyway? Bare sidewalks and inconsistent signage turn navigation into a guessing game. Choose early mornings, or choose a car.
3. Houston, TX
With few protected bike lanes and hostile intersections, riding here often feels like crossing a moat of SUVs. Bayou trails exist but rarely connect to job hubs. Add in 100-degree summers, and you're sweating bullets while dodging fenders and potholes.
4. Chicago, IL
Chicago, despite its progressive reputation, has bike lanes that get plowed under in winter, if cleared at all. Door-zone striping along Milwaukee Avenue creates daily close calls. Icy intersections and distracted drivers make riding feel like a Midwestern obstacle course.
File:Chicago River ferry.jpg: John Picken derivative work: Georgfotoart on Wikimedia
5. San Bernardino, CA
Neglect tells the story here. Crumbling pavement and scarce lanes in San Bernardino leave riders out to dry. Infrastructure investment is minimal, and bike racks are rare. Cyclists often hug gutters on six-lane roads, where 50 mph feels routine.
6. Jacksonville, FL
Design in Jacksonville favors speed, not safety. The deadly mix of highways, few shoulders, and disconnected lanes makes cycling risky. Only the bold dare ride Beach Boulevard. When Florida led the U.S. in cyclist fatalities in 2023, Jacksonville played a big role in it.
7. Santa Ana, CA
Cars rule every inch. Santa Ana lacks a cohesive bike network, and this leaves riders to gamble at chaotic intersections. School zones and neighborhoods remain underserved. In 2021, a cyclist was hit outside Santiago High—no buffer, no signage.
8. San Elizario, TX
Unincorporated and underfunded, San Elizario offers little bike access. No dedicated lanes and long distances between essentials make it an uphill battle, figuratively and literally. Even nearby El Paso overshadows it. Spotty lighting is also an issue here.
National Trails Office (US National Park Service) on Wikimedia
9. San Antonio, TX
History's preserved in San Antonio, but safety's not. The downtown River Walk forbids bikes in many stretches, and outer neighborhoods lack basic infrastructure. Connectivity gaps are everywhere. Cyclists navigating Culebra Road share lanes with semis; zero protection. Cyclists will need more patience and caution here.
Biking The San Antonio Mission Trail - A Fun Couple's Activity in Texas! by The Places Where We Go
10. Miami, FL
Sunshine doesn't fix broken streets. Miami's flashy image hides a mess of potholes and high-speed arterials. Even designated bike paths like Rickenbacker Causeway see regular accidents. You might get views, but you can also get clipped if you're not hyper-alert.
