25 Great Portland Bike Rides

What's your history with biking?
When I was 7, my dad pushed me down a logging road in Cottage Grove, Oregon, where I grew up. I skinned a few knees before I got up and running. Then I had a paper route when I was 14, on the logging roads of Cottage Grove again. In high school I rode my bike to school as much as I could. During that time I got in trouble with a bus driver for riding without my hands on the handlebars. My freshman year in college I bought a road bike with money I was supposed to use for tuition. Later, I took a mountain bike to Rome, Italy, where I was living teaching English. I've worked as a bike messenger very briefly in Seattle. In San Diego I organized a bike to work day with a bunch of coworkers who, quite frankly, hadn't ridden bikes since they were children because really no one bikes there. And now here I am!
What's up with the "No Spandex Required" motto?
Everybody has this idea that you have to be as good as Lance Armstrong or you shouldn't even bother to get on a bike. Off the top of my head, there are probably 290 million people who don't ride bikes regularly and only 10 million people who are avid road riders. I'm really trying to reach out to people who are sitting on tour buses and couches. It's that battle of trying to show people that bicycling is easy, safe and fun. At our bike tour company we get people that ask, "Should I be using my clipless pedals and wearing my riding shorts?" The answer to those questions, and the same is true of the book, is no! Take that old rusty junker out of the garage, grab this book, and go explore!
What's the best part of biking in Portland?
The constant discovery, and rediscovery, of the beauty of the city: the architecture of the houses, the great little shops, restaurants and bars that are to be discovered in each neighborhood. Also the camaraderie of seeing other bikers riding around. I really enjoy the quirkiness of the people who like to ride here. You see dogs in baskets, little kids with propellers on their helmets, and people in wacky socks or crazy skirts. All those things make it fun to ride here.
What was your approach to this book like?
I took out a big map and my goal was to create a loop ride in every quadrant of that entire map. I started with the easy places like the neighborhood by my house. Then I basically connected every park I could find and any retail district I could find and used the bike map to find the safest route between those. At the same time I was trying to create loops with as few turns as possible and as little elevation gain as possible. It was like putting a jigsaw puzzle together as all these little loops just appeared on my map one by one until I had covered everywhere that I could.
The book has this fun element where you recommend scavenger hunt items that riders should keep their eyes out for, what is your personal favorite scavenger hunt item?
It would have to be the dragon driveway gates in Oak Grove. They're the coolest gates. They're both these silver and copper dragons and their eyes are electrified, one is red and one is green. You really have to be looking to find them or you'll just miss it.
Todd's Top 3 Rides
Ride #25: Oregon City to Gladstone
This 10.5-mile loop begins in the heart of Oregon City and offers a chance to check out the rejuvenated Main Street and historic waterfront before riders hop onto the Oregon City Elevator to catch views of the rushing Willamette Falls. Later, bikers will cross the Clackamas River on a car-free bridge and meet up with the Trolley Trail, a historical trolley line that's been converted into a multi-use path. From there the loop continues on through Gladstone toward man-made Clackmette Cove, with an optional off shoot to explore the notoriously dangerous swimming hole known locally as High Rocks.
Ride #24: Oak Grove and the Trolley Trail
Great for architecture buffs, this 8.5-mile ride leads bikers along the Trolley Trail, a historic trolley line that's been transformed into a multi-use path, and River Road's pleasant bike line. Once adventurers are about 5 miles in, views of amazing architecture and suburban mansions abound as the loop follows the Willamette River and leads bikers by a hidden lake. Don't miss the pair of ornate dragon driveway gates guarding the estate that once belonged to Will Vinton, director and producer of animated films such as The Adventures of Mark Twain and Return to Oz.
Ride #6: Beaverton's Ponds, Parks, and Power Line Trail
The beginning of this 10.5-mile loop leads riders on a variety of car free paths and meanders through several parks including: the sports complex at the Tualatin Hills Parks and Recreation Center, the boardwalk traversing a wetland nestled between residential neighborhoods, and a staggering seven duck ponds. Later, the ride hits the road to explore farmland-turned-residential areas. Keep eyes peeled for a quick glimpse of the 193-acre Nike World Campus nestled in the heart of Beaverton.