Back in May, a few of us hopped on a ferry and set sail for the nearby Bainbridge Island to meet up with Rick Hauptman, a local cycling legend and the creator of the Dirty Chilly bike route. Rick designed this route to mimic the classic Bainbridge road ride, the Chilly Hilly, but with an emphasis on the abundant trails and gravel roads that weave throughout the island. After leading us around to some secret spots (including the ruins of a possibly haunted house) we sat down with Rick to get more insight into the history of the Dirty Chilly and his time in the Seattle area.


Okay, Rick. We’re here! First of all, thanks for joining us today. First question: How’d you get into cycling? Let’s back up. Where were you born? What’s your history? What brought you to Bainbridge? 

I was born in New England. I was living in San Francisco, and I got tired of that. I bought an old vintage Triumph motorcycle and just drove up the coast. I had a friend who lived up here. I’d grown up summers on the beach on the salt water. I wanted to live near salt water, so I just came up here. It reminded me of summers as a kid. So, I’ve been here ever since. Moved up here a couple months after Mount St. Helens blew up. At that time I wasn’t riding bikes, I was riding motorcycles.

What’s your relationship with the bike? How did it begin? Where are you at now? 

I got into bikes through commuting originally. Now, I like to participate in as many manifestations of bike usage as I can. I think typically, I love being able to commute by bike. That’s really great. I love being able to camp and get out into nature. Those are probably my top two. I’ve done some racing, road riding, tried a little bike polo, a little this and a little that. I just enjoy connecting with different bike-centric communities. 

Can you give us some background on the Dirty Chilly and how that became a thing? When did you first make that route? 

Yeah, sure. As everyone knows, the Chilly Hilly is an iconic Northwest race created by Cascade Bicycles. I lived on the island, previously, for a number of years. There’s a lot of great trails. The parks department is really great on Bainbridge, and they create a lot of trails. There’s also a lot of informal trails that citizens have just created on their own. People have ridden bikes for many many years on Bainbridge, and a lot of people have been coming over from Seattle to ride bikes on trails and dirt/gravel roads. There are many different, interesting paths and trails on the island, and so I thought it would be a fun challenge to create a different version of the the Chilly Hilly. 

In recent years I’ve gotten more into riding off road, so I thought wouldn’t it be kinda fun to have a different version of this classic route for people who want to do the Chilly Hilly but don’t want to be on the road? If you look at the two routes, at first glance they are almost the same. So, one of the things was to try and make it very similar to the Chilly Hilly in terms of the general direction and all that except make it as much trail as possible.


I started working on it four or five years ago. I think it’s been a ride with friends for the last three years or so. The first spoke card was like 3 years ago. I tweaked the route every year to make it a little bit longer. Currently it is about 40 miles: half gravel, half road. When I say gravel I mean trails and gravel. 

It’s really cool, if you live in Seattle, and you want to ride off road, to be able to take the ferry and go ride in the woods and get back in a day [without a car]. It’s probably the closest, easiest thing you can do as opposed to putting your bike on a car and driving to the East Side. I thought this could be something I could give to people. Everyone kind of knew little trails and stuff they could do, but I was able to spend the time to put together a route that copies the Chilly Hilly, but also optimizes all these little routes and backyard pathways that a lot of people didn’t know about. But also do things like gain most of the altitude on asphalt, the easy stuff, and have the downhill on trails. To have it all stitched together, have it flowing, stay off the roads as much as possible, and have it be something really fun so people could come over and have a good time and not have to figure it out. After I did [the Dirty Chilly] there were a lot of trails at the south end [of Bainbridge] I really love, so then there was the Dark Chilly that was a separate project. It was the same thing. Like, these trails are so cool! If you have less time you can do that one. It is a bit more mountain bikey, though. 

How do you envision route building? Do you feel like it’s a form of expression for you? 

It’s like puzzle solving. I think I definitely spend a lot of time putting this together. Each year making little tweaks to improve it. Sometimes new trails appear that weren’t there before. We went on one of those today! Figuring out something that is the basic shape of the Chilly Hilly and has a nice flow to it was a puzzle.. 

Do you have a process that you follow for scouting these trails? 

I just wander around and ride. “Oh there’s a trail! Where’s that go?“ The bailout route took me three months to figure out. I knew it was there but I couldn’t figure out where it connected. I had to knock around a bit to hunt that down. In the very beginning I used some tracks to remember and stitch it together, but now I can mentally go through the whole route in my head. 

What do you look for most when building routes? The cutty trails or the secret spots? 

I like to make it as interesting as possible which includes view points if I can. I try to avoid stuff that is gnarly and more for mountain bikes. Something that is more accessible. I put it in the notes of the rides what the general tenor is: what kind of tires you might use, etc. 

Have you seen the Dirty Chilly form a community around it? How does community become involved in the route? 

We typically do a rally ride the day before the Chilly Hilly (February). I think there were like 50 or 60 people last time. The first time we did it there were a dozen people. I don’t really want to be an organizer for the event really, because I don’t want to be responsible. 

Well, thank you Rick. I really appreciate it!

Yeah! Very fun riding with y’all!


Check out the route here: 

Dirty Chilly – extended edition (2023)