Jan 012020
Challenges: Bike Challenges to Try in 2020

Maybe you’re a plan-ahead-er, maybe not. Maybe you’re a mileage tracker, maybe not. This list works for you either way: as something that makes you head straight to your calendar and enter dates for all of these, with a reminder to check back in advance of some of that haven’t been scheduled yet, or as something you bookmark thinking, “Yeah, maybe?”

Whatever system or lack of a system turns your cranks, this is your list.

First, what this is most definitely NOT as a list of bike events —

This is not the “Ultimate Cycling Challenges List” that requires you to ride straight up mountains really fast.

It’s also not the “Best Bike Challenges You’ve Never Heard Of” list, although I’d love to learn about bike challenges I’ve never heard of that fit into my very loose parameters. Leave those in the comments and I’ll add them to the post.

It isn’t “Bike Fitness Challenges for Your Health“, although bicycling is certainly good for your health.

What it is: A roundup of the kinds of bicycling challenges with low barriers to entry that can build a sense of community through participation in a shared endeavor. Just say you’re doing it. No entry fee, maybe some prizes and maybe not. A bit of logging required if you want to actually prove you participated. (Writing things down makes us more likely to follow through.)

I’m posting this in January so you can plan ahead. Some dates are listed as TBA; I’ll come back and update as they’re announced. I’ll also add other challenges as I find them, so bookmark this and check back each month if you’re the tracker type. (Hey, you could put this on your calendar as a to-do. Or send yourself an email but delay delivery until a relevant date.)


Any time during the cold months, really: Icy Bike Winter Commuting ChallengeThis functions as a Facebook group; you sign up and log your miles and weather conditions.

Errandonnee, dates flexible: DC rider/blogger/Inventor of Fun Informal Challenges Mary Gersemalina created errandonnee in a mash-up of errand + randonneuring. The 2019 errandonnee post will give you an idea of what’s involved — rules get tweaked a bit each year. Basically you bike (or run, for Errundonnee) to a variety of destination types over a specific time period and reach the target mileage total.

This is the month to figure out when you want to tackle Errandonnee if you’re a plan-ahead-er. Beginning in 2020 Errandonnee season will start in mid-January and go until March 20 or so. You choose 12 consecutive days within that window to complete 12 errands by bike (or running, if you want to work that hard).


Feb. 7, 2020: Winter Bike to Work Day. Always the first Friday in February.

Feb. 13, : Here’s an idea: Organize a Valentine’s Day version of for your local food bank. This doesn’t mean you clean your pantry and donate cans of food you didn’t want that may be past their expiration date. Instead everyone get together, ride to a local food bank, tell them you love them (it’s Valentine’s season), and give them some money.

Here’s why if you want to watch an episode of Adam Ruins Everything; or you can take my word for it that this is a good idea; or you can recognize that food banks get a lot of attention in holiday season but people need to eat all year long and donating to food banks at a different time of year is a big help.

I’m calling it for now because people who bike love food, giving food represents love, and of course because Valentine’s Day. I’m going to assign it the second Saturday in February, which should always fall somewhere around Valentine’s.

And of course, if you decide to start Errandonnee sometime this month, biking to donate checks a box.

March: Still cold where you live? Maybe you jump into the Icy Bike Winter Commuting Challenge now if you didn’t in January because starting new things in January is such a cliche.

Make or break month for Errandonnee: If you didn’t take the hint in January or February you need to get rolling to complete it before the cutoff date.


Hand-drawn upright turquoise bicycle with lettering that reads Happy April! #30daysofbiking. By Melissa Balmer, PedalLove.com

#30DaysOfBiking: So easy. No, really. Just ride every day. Totally counts if you ride to the end of the driveway and back, put your bike on the trainer and spin while you binge on Netflix or Hulu, take a quick Tour de My Block  — however you turn your cranks, it counts.


Bike Everywhere Challenge: Near and dear to my heart, considering I worked on Bike to Work Week celebrations as some of my first bike advocacy in Spokane and this put me on the path to a change of city and more than one career change.

May is recognized as National Bike Month with a nationwide challenge promoted by the League of American Bicyclists that continues for several months. In Washington we call it #BikeEverywhere Month and Washington Bikes runs a statewide challenge, and Cascade Bicycle Club helps Washingtonians find any challenges in their hometowns. I sign up faithfully every year and ride. How could I do otherwise? (Whether or not I actually log my miles is a separate question.)

May 6: National Bike to School Day. Good for teachers, principals, aides, volunteers, coaches, parents as well as kids! Register your school, maybe help lead a bike train so more kids can roll.

May 9-10: Cyclofemme. Challenge meant to inspire women to invite other women to ride with them on the weekend that includes Mother’s Day in the US. If your area doesn’t have an organized ride, you’re reading this so maybe you become the organizer. (Which checks a box on the #BikeIt list.)

I love the Cyclofemme statement of inspiration — WE BELIEVE: That strong communities are built around strong women. That being on a bike brings us closer to our community, to nature, and to ourself. That from action comes change. That our hope, courage, and strength is amplified when we unite.

May 11-15: National Bike Week. Some places set their own dates for this. As I repeat quite often, join your local/regional/state/national bike organization. That way you’ll get news about this and so much more.

May 15: National Bike to Work Day. Always the third Friday in May.


National Bike Challenge continues.

You could also make this a month to keep rolling from #BikeEverywhere Month.


National Bike Challenge continues.


National Bike Challenge continues.


: The original organizers don’t always promote this, but 30 days hath September, as the rhyme goes. (Some of you use this one weird knuckle counting trick to work out how many days in a particular month. I use the poem.)

National Bike Challenge continues.


Dates TBA: Coffeeneuring usually falls somewhere in this time frame. Another Mary Gersemalina creation, this is randonneuring for coffee and/or other beverage. The 2019 rules give you an idea of what to expect. I completed coffeeneuring successfully in 2019 and other years thanks to my love of caffeinated beverages, and I’ll be on this again in 2020.

Walktober/Biketober: To change things up a bit you can also challenge yourself to walk more in October. Look for Walktober events and National Walk to School Day October 7.

BikeOWeen: I’m declaring this one an official holiday. Instead of driving kids around and contributing to the single biggest day all year for drivers to hit and kill children with their vehicles, why not roll out for goodies on your bicycles? Family bike, cargo bike, kids on trikes — couldn’t be cuter. Organize a bike train with friends, neighbors and family to add to the cuteness and contribute to the “safety in numbers” phenomenon.

As a parent you’ll feel marginally better about the sugar consumption knowing that they had to work for it a bit and you bring down the risk of a deadly crash through the simple act of not driving. (True story: Reducing vehicle miles traveled is listed in the Highway Safety Manual as a proven countermeasure, meaning research shows this helps reduce the number of serious and fatal crashes. A mile not driven is a mile not running into anyone with a steel box weighing two or more tons.)


All month long: #RideInTheRain. This one is promoted by Washington Bikes but there’s no reason it has to be confined to the Evergreen State. Note: No requirement for actual rain affecting the length or timing of your ride.

Nov. 21: #Cranksgiving. The Saturday before Thanksgiving, ride your bike to collect food for food banks. This food drive scavenger hunt by bike doesn’t happen in your town? Well, you have nearly 11 months to plan, promote and make it happen. Tom Fucoloro of Seattle Bike Blog gets it rolling in Seattle, and people organize it in Port Angeles, Sequim, Tacoma and West Seattle. Find your town on the map.

Better yet, do this at a time of year other than the winter holidays. People need to eat year round. And before you donate any canned foods, watch Adam Ruins Everything on canned food drives and why you might decide to ride your bike to the food bank and give them some cash instead, or at least not treat this as an excuse to clean out your pantry and get rid of food you wouldn’t eat yourself.

Note that the Cranksgiving organizers are savvy: They put together lists of things to purchase so you’re not donating old bulging cans of that oddball ingredient for a recipe you decided not to make. But even fresh foods require storage and that costs money. Your donated dollars will go farther spent by the food bank staff than the boxes of stuff you buy at full retail prices.


: This popped up this year in the Love to Ride app you’ll already be using for #BikeEverywhere, #RideInTheRain, and National Bike Challenge.

Depending on where you live December might also be when you realize you’re participating in the Icy Bike Winter Commuting Challenge.

Others ways to construct a challenge

However you get rolling, bicycling offers challenges and tracking of various levels of difficulty and complexity.

How about you? Are you a tracker? Like/love/hate/ignore challenges? What structure or theme motivates you, if any?

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