6 Most Bike-Friendly Towns in Oregon
As the second most bikeable state according to the League Of American Bicyclists, Oregon is packed with pedal-worthy places. Sure, Portland is renowned as a biking mecca, as are Eugene, Bend, and Corvallis, but even Oregon's smallest settlements are bike-friendly. From an iconic filming location turned covered bridge trail to a sea-blasting beach ride to a 5,000-foot drop from a ski area, these six lower-key communities have some of the state's highest, longest, and prettiest pedaling paths.
Cottage Grove
You might be tempted to do a lot of things in Cottage Grove before biking. You might want to stand and admire the city, since it was one of the filming locations for Stand by Me, or walk like the characters do across the Mosby Creek Railroad Bridge. However, the tracks are gone, and in their place are miles of extremely bikeable pavement as part of the Row River National Recreation Trail, which is itself part of the Covered Bridges Scenic Bikeway, a 35.8-mile loop with six covered bridges. These include the Chambers Covered Bridge, Dorena Covered Bridge, and Stewart Covered Bridge.
In addition to bridges/filming locations, the bikeway passes darling Dorena Lake and the unincorporated community of Dorena (which has the Baker Bay Bead Company), historic downtown Cottage Grove (where you can stop at Rainy Peak Bicycles and Stacy's Covered Bridge Restaurant), and ends at tranquil Trailhead Park.
Cascade Locks
You will probably need less convincing to bike around Cascade Locks. This small city occupies one of the most bikeable places in Oregon: the Columbia River Gorge. Starting at the Bridge of the Gods, which crosses said river at the southwest end of town, the Historic Columbia River Highway State Trail is a car-free path to gorgeous sights, especially the Eagle Creek Canyon and the John B. Yeon State Scenic Corridor, both of which sit west of Cascade Locks (another section of the Historic Columbia River Highway State Trail starts east of town). You can traverse the trail on a traditional pedal bike or book an electric bike from Bike the Gorge, a rental and tour company in Cascade Locks.
Moreover, mountain bikers can get their kicks on the Cascade Locks MTB Trails. Cascade Locks was the fifth highest-ranked Oregon community on PeopleForBikes' 2024 bike-ability list.
Milwaukie
Milwaukie was also ranked the fifth most bikeable OR community but from a different company. Redfin is a real estate org that selects the most bikeable cities in various states, and Milwaukie landed fifth on its 2024 Oregon list. Its reasons include bike-friendly Riverfront Park and the Trolley Trail, as well as bikeable businesses like the Breakside Brewery & Tasting Room and those at the Milwaukie Farmers Market. Although plenty of residents ride for recreation, many ride to work.
Out of Oregon cities, Milwaukie has the fifth-highest percentage of bike commuters, according to a 2020 Oregon Live article based on census data. Some even ride for work, such as the cops assigned to the Milwaukie Police Bicycle Fleet.
Bandon
PeopleForBikes put Bandon one spot ahead of Cascade Locks for Oregon bikeability. Though also a small city, Bandon has a much different terrain since it stretches along the Pacific Ocean. Not only can you ride along the beach in Bandon via the Beach Loop Road, you can ride on it! The Bandon Fat Bike Beach Ride takes fat tire cyclists through sand and surf for 19 miles.
If mountain biking is more your speed, enter the Whiskey Run Trail System, which comprises 12 miles of scenic yet challenging trails with such names as Sour Mash, Dirty Dishes, and Captain Blacklock. Whiskey Run is a work in progress, so those 12 miles are expanding to 30. Hopefully, that goal will be reached in time for the next Ride the Dirt Wave, an annual competition and celebration at Whiskey Run. Information packets are handed out at South Coast Bicycles, which has been serving Bandon's diverse bikers for over a decade.
Hood River
Hood River is another compact Oregon city with enough sprawling trails to make PeopleForBikes' bikeability list. Located east of Cascade Locks in the Columbia River Gorge, Hood River abuts the other section of the Historic Columbia River Highway State Trail. This 4.5-mile car-prohibited chunk is called Twin Tunnels Segment and takes cyclists into the namesake tunnels alongside wildflowers and wonderful river overlooks. A longer and perfectly named riding route is the Hood River Fruit Loop, which passes orchards of pears, apples, and cherries that you can taste and even pick yourself.
Mountain bikers are treated to 140ish miles of trails in the nearby Mount Hood National Forest. Before setting out, rent gear and join tours at Hood River Mountain Bike Adventures in Hood River proper. Enthusiasts will also want to sample at the eatery, KickStand Coffee & Kitchen, which was founded by professional mountain bikers Kim and Nick Hardin. The Hardins lead mountain bike rides from their café.
Ashland
Ashland topped PeopleForBikes' ranking of bikeable Oregon cities. Not only that but it was rated 27th among all American cities and 13th among American cities with fewer than 50,000 residents. Though home to just over 20,000 people, Ashland claims 50-plus miles of trails for road bikers, mountain bikers, and gravel bikers.
Road bikers enjoy the paved Bear Creek Greenway, which extends for 20-plus miles from Ashland to Talent to Phoenix to Medford to Central Point; mountain bikers conquer the Mt. Ashland Super D, which begins via shuttle at the Mt. Ashland Ski Area and then exposes cyclists to a 5,000-foot decline before landing them back in town; and gravel bikers grind parts of the 28-mile Ashland Watershed Loop. The most adventurous riders take the Cascade Siskiyou Scenic Bikeway, a 55-mile eclectic expedition that starts and ends in Ashland.
Although Oregon is well known for its bikeability, some of its smaller communities are unknown to biking laymen. Cottage Grove, Cascade Locks, Milwaukie, Bandon, Hood River, and Ashland all have small populations but many miles of incredible trails, including the Covered Bridges Scenic Bikeway, Historic Columbia River Highway State Trail, Trolley Trail, Bandon Fat Bike Beach Ride, Hood River Fruit Loop, and Mt. Ashland Super D. Those are paths that every capable person should pedal. Go to Oregon for an overlooked biking vacation.
