[Read all of the articles in our Portland Fun Guide HERE! Looking for a print copy? Look at this handy-dandy map!—eds.]

Everyone knows Portland is a great city for biking. But once you have your bike, and you’re on the street getting ready to push the pedals, you may find yourself wondering: Where should I go? 

The Portland Bureau of Transportation (PBOT) offers a very helpful list of suggested rides on its website, with information about the length and geography of the route. What PBOT’s suggestions don’t include, however, is an explanation of WHY you should go on any given bike ride. This short list provides a starting point for developing your own favored bike rides around the city. 

Disclaimer: While I would love to tailor these recommendations to each individual reader, I don’t know where y’all live or are starting/ending your bike rides. I highly encourage you to check out PBOT’s biking and walking maps, which show the city’s greenways and bike routes. (Your preferred GPS app will also typically be pretty accurate when it comes to bike directions.)

The St. Johns Ride: For when you want to find serenity underneath Portland’s most beautiful bridge. 

If you don’t live in the North Portland peninsula, I bet you don’t go to St. Johns enough. The neighborhood—home to some very charming houses, the city’s most gorgeous and iconic bridge, and great cafes and restaurants—is also easier and safer than ever to access by bike. Last summer, PBOT made some key changes to North Willamette Boulevard, removing on-street car parking and fixing a gap in the bike lanes. (The city has plans to make the street even better for biking, so stay tuned.)

North Willamette Blvd contains some of the best views in the city, showcasing the northern stretch of the Willamette River and the bluffs that surround it. Once you arrive at Cathedral Park, enjoy the scene of the St. Johns Bridge with Forest Park’s trees behind it. Depending on the time of day and year, you might be accompanied by some cute ducks and geese, or people swimming at the new Cathedral Park dock. 

Recommended route: Coming from the east, take North Rosa Parks Way, which turns into N Willamette Blvd a few blocks west of N Greeley. From the south, take N Greeley past Mocks Crest Park and the Dog Bowl until it meets up with N Willamette. Take Willamette northwest to North Burlington, where you’ll turn left to arrive at Cathedral Park. The route along Willamette is mostly flat, but don’t be ashamed if you have to walk your bike up Burlington when you’re ready to go home. 

Pit stop ideas: Get a caffeinated pick-me-up at the wonderful Cathedral Coffee on N Willamette and N Buchanan. (Open seven days a week, 7 am to 5 pm.) In St. Johns, make a detour up to the corridor along N Lombard for excellent Mexican food at Tienda Santa Cruz (8630 N Lombard, open 9:30 am to 9:30 pm every day), renowned—if elusive— pizza and ice cream at Gracie’s Apizza (7304 N Leavitt, open Thursday to Saturday 5-8 pm), or a drink and a show at The Fixin’ To (8218 N Lombard, open every day from 4 pm to 2 am). 

The author biking up the Marine Drive trail. Cameron Crowell

The Sugarpine “Bike-In” Ride: For when you want to work for your ice cream sundae. 

First, let me be clear. I believe eating ice cream is a human right, and don’t think you should have to physically punish yourself in order to enjoy a sweet treat. But it’s also true that a good meal tastes at least ten times better after a long bike ride, and this is particularly true of the Sugarpine Drive-In. 

Sugarpine is an adorable little diner serving up scrumptious, soft serve ice cream sundaes and sandwiches on the Sandy River in Troutdale. It’s also located right off the 40-Mile Loop, an incomplete series of bike paths and trails circling the Portland metro area. Don’t let the restaurant’s name mislead you—while Sugarpine does have a drive-thru, there’s also a walk-up counter, and it’s perfectly bike-friendly. 

Suggested route: When traveling all the way to Troutdale by bike, the journey is a major part of the experience. Luckily, this journey is quite lovely. The Marine Drive Trail takes you most of the way there, overlooking the adjacent Columbia River. Facing east on a clear day, the Marine Drive Trail provides some of the best Mount Hood views you can find in Portland. There are some gaps in the trail, however, meaning you’ll have to ride on NE Marine Drive’s somewhat sketchy bike lane for chunks of the trip. I recommend getting to the trail via NE 33rd, which you can approach from the west via NE Dekum. However, take care when crossing the weird bridge over NE Lombard and Columbia. Then, stay on NE 33rd Drive until you see the trail entrance. (You’ll pass a golf course and the Columbia River Correctional Institution on the way.) Enjoy the plane spotting opportunities the trail presents when passing the airport, if you’re into that kind of thing. 

At NE 223rd, take a left. You’ll run into the new Ch’ak Ch’ak Trail, which runs around the Troutdale Airport and Amazon PDX9 warehouse. When the trail ends, take NE Harlow Road to the path under I-84 and ride on the Crown Point Highway before crossing the Sandy River Bridge, where you’ll run right into Sugarpine. 

Enjoying the view at Mocks Crest Park. Taylor Griggs

The first date ride: For when you need a route to romance. 

If you’re on the dating apps in Portland, someone very well may suggest going on a bike ride for your first date. Bike rides can make for good, endorphin-boosting first dates, but you probably want to avoid a route that will leave you gasping for air and sweating. This route, which takes you between two of Portland’s finest parks, is relatively flat and contains many opportunities to stop and catch your breath. 

Suggested route: Start at Irving Park on NE Fremont and 7th. From there, take NE 7th to NE Shaver to North Williams, where opportunities for refreshments begin to emerge. Continue on Shaver to N Mississippi, which is home to some of the best first date spots in the city. Then head south one block to N Failing, which will carry you across I-5 to North Overlook. Stay there until N Skidmore, which will deposit you at Mocks Crest Park (AKA the Skidmore Bluffs). If biking to Mocks Crest on a first date is too basic for you, go to the Dog Bowl instead, located on N Willamette and N Jessup. Or pedal back to N Shaver. Take a right on N Michigan and head north to N Ainsworth, where you’ll find Peninsula Park (and, in the right season, its fountain and rose garden). If even that’s too basic, go back to Irving Park. Take NE Klickitat east to NE 18th, and head north until you reach Sabin HydroPark. Or stay on Klickitat and ride east until you fall over. (That’s what you get for criticizing my bike ride ideas.) 

Pit stop ideas: Kulfi is a unique dessert shop on Williams between Fremont and Beech, selling delicious ice cream and its namesake Indian frozen treat. On Mississippi, check out Moloko, Interurban, or The Rambler, which are each romantic in their own way. I also recommend gazing into the mesmerizing display at Sunlan Lighting. Tehuana Oaxacan Cuisine, a food truck on N Ainsworth and Greeley, is worth the detour. 

The Goodwill Bins Ride: For when you want to bike along the Willamette on the Springwater Corridor trail, but feel like you need a destination and don’t want to go to Oaks Park. (This ride could also be the Oaks Park Ride with very few tweaks.)

I love the Goodwill Outlet Store (AKA The Bins) in Milwaukie, as does every cool person in Southeast Portland, many of whom are intimidating. Build up the strength and confidence to fight for your finds at the bins by riding your bike there. 

Suggested route: This one’s easy: Just take the Springwater Corridor trail (the segment adjacent to the Willamette River) south and keep going. From the trailhead just south of the Tilikum Crossing Bridge, the ride is about four miles, and pretty much flat. You’ll pass Oaks Amusement Park and the Oaks Bottom Wildlife Refuge, both of which offer visual interest. Head east off the path at SE Linn Street. Goodwill is across SE 17th Ave, and there’s bike parking up front. If you buy too much stuff, there’s a MAX Orange Line stop a few blocks away. 

Pit stop ideas: Piece of Cake bakery, on SE 17th and Umatilla Street, is charming and yummy. The Muddy Rudder Public House, right off the Sellwood Bridge, is welcoming with great pizza. Lady Gaga once went to Gino’s, on SE 13th and Spokane. But if that’s too upscale for a post-thrifting bite, try the Sicilian deli and bakery Sebastiano’s, located on SE 13th and Umatilla. There’s a lot to check out in Sellwood—if you’re not already making regular trips to the neighborhood, an afternoon biking its streets will make you want to change that.