“Best” is a pretty subjective term. Everyone’s got different criteria and everyone’s got different ideas, so what might be amazing for one person could be nightmarish for another. That’s one reason why the comments sections of “best of” lists are so … lively.

Taking that into consideration, I’ve curated a list of “really great” places for different types of cycling. While these are my recommendations, there are plenty of solid options across the country. As always, feel free to share your vote in the comments section.

1. Great City for Off-road Cycling: Moab, Utah

Mountain cycling may’ve gained popularity in lush and temperate Northern California, but you’d be doing yourself a huge disservice if you didn’t get inland to Moab. It might not fit your typical idea of a “city,” but it’s got everything an off-road cyclist could want.

Mountain cyclists should try the Whole Enchilada route, which plummets 6,000 feet from high-alpine singletrack to desert rock and sand, with everything in between.

More of an explorer? Moab has 2 national parks, a huge state park, and Bureau of Land Management-preserved land as far as you can pedal (and further). Add plentiful camping and all-around affordability, and you and your 29er may never leave. As a bonus, Park City’s only 240 miles away and has over 400 more miles of singletrack.

2. Great City for Steep Climbing: San Francisco, California, and Pittsburgh, Pennsylvania (tie)

I lived the first 17 years of my life in Pittsburgh and the last 24 in San Francisco. But it’s not personal bias that made me choose these 2 cities as brutal tests of your quads — they’re probably 2 of the hilliest urban centers in the U.S. Between them, they have 4 of the steepest streets in the country, none of which fall below a 31 percent grade and the steepest at 37 percent.

San Francisco’s so steep that it has dozens of “wiggles,” which are left-right-left-right routes around imposing climbs. The city identified one of these wiggles on its official cycling map and even added route signage to help casual cyclists keep their heart rates down.

Pittsburgh has an annual 50-mile ride called the Dirty Dozen, in which participants ride up 13 of the city’s most inclined streets, including Canton Avenue, the steepest street in the continental U.S.

As 5-time Giro d’Italia and 2-time Tour de France winner Fausto Coppi once said, “Cycling is suffering.” So pick a coast and give one of these great cities all you’ve got. For extra respect from the locals, try to conquer some of these monsters on a single speed or fixed-gear bike.

3. Great City for Road Cycling: Nashville, Tennessee 

You can’t limit road cycling to a single city, but great starting and ending points are crucial. Depending on which direction you’re traveling, Nashville is either the starting point or the finish line to the amazing 444-mile Natchez Trace Parkway. This single road stretches from Nashville through Alabama all the way to Natchez, Mississippi, and the entire route is designated by the National Park Service as a bike route.

There is no commercial traffic, there are no stop signs or lights, there are restroom facilities every 20 miles, there are bed-and-breakfasts located throughout, and the vistas and historical attractions along the way offer a seemingly infinite amount of things to look at or learn from.

Choose a short portion of the route or do the whole thing over multiple days. No matter how you do it, you’ll either start or end your ride in the musical mecca of Nashville, responsible in part for launching the careers of everyone from Johnny Cash to Miley Cyrus.

4. Great City for BMX: Austin, Texas

Yes, New York City’s level streets and transit considerations make it easier for BMXers to travel between its hundreds of concrete and steel obstacles. But I like Austin for its mix of street and dirt and great weather year-round (never mind its amazing music scene and let’s face it — barbecue).

There aren’t many better dirt-jumping spots than Austin’s iconic 9th Street Trails. And the pools, ramps, ledges, and rails of the 30,000-square-foot Austin BMX and Skatepark put Mabel Davis, previously known as the best skate park in town, to shame.

Austin’s got a surprising number of street spots as well. From the 5-Hip Ditch to the brutal Austin Church Gap, this capital’s appeared in dozens of BMX videos for a reason. It’s also home to one of the largest BMX parts houses in the country, Empire BMX, where you can go ask about more spots than I’d ever be able to list here. And if you’re tired of 20-inchers for the day, Austin welcomes cyclists of all disciplines. It’s generally known as one of the all-around bicycle-friendly cities in the nation.

5. Great City for All-Around Cycling: Portland, Oregon

Portland’s unique because it appeals to all types of cyclists. From kitted-up roadies on $10,000 custom Moots to backyard welders with double-high tall bikes, you’ll see it all in Portland.

Whether it’s the great mix of terrains or easygoing vibe, Portland sets the mellow pace of pedaling your Saturday afternoon away. It’s so desirable to so many cyclists that the city’s created so-called “bicycle boulevards,” where bicycle traffic has priority. Just be warned that Portland’s wet, wet, wet, so bone up on rain riding first.

Two fun facts that confirm the area’s love for cyclists? Portland has a bicycle moving company that uses electric-assisted cargo bucket bikes to get your couch and TV across town. Or, if Portland’s your last stop on this great ride we call life, you can arrange one final ride in Eugene (100 miles south) where one funeral home offers a bicycle hearse.

I sincerely hope some of these great places make you want to go out and ride. If they do, keep the rubber side down! Unless you’re a BMXer. That would be pretty boring.

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Travel hacks | Destinations


about Blair

Blair, widely considered the Esurance expert on all things cycling, is obsessed with pedal power. When he's not doing ludicrous things like riding from San Francisco to Los Angeles on a bike with only one (fixed) gear, he's busy using his 10+ years of experience to create award-winning design work for Esurance.