Portland is frequently called America's biking city, but you're wondering where the best places are to try a casual urban cruise. Bicycle boulevards crisscross tree-lined neighborhoods dotted with cafes, vintage boutiques, craft breweries, and movie pubs. No mode will guide you to these destinations more quickly and wonderfully than a bike. Unless you’re confident in traffic, skip downtown and head right for the east side.
Just a dozen blocks from the Hawthorne Bridge, get lost in Ladd's Addition before heading southeast to SE Clinton & 21st Ave. Take a left and head uphill. See the bike symbols in the road? This means you're on a bicycle boulevard where you're welcome to bike in the middle of the lane. Stop signs have been removed for your rolling pleasure. At SE 41st, take a left and head north. At Hawthorne, colorful businesses (House of Vintage, Powell's, Backstage Pub) stretch west down the street for miles. Soak up the area on foot or continue north to Ankeny St.
Your legs will get a rest on the downhill ride along Laurelhurst Park. At SE 3rd Ave, take a left and head south through the packing district. The bars in this neighborhood are far less divey than a traveler might assume (Produce Row). At the Hawthorne Bridge, connect with the Eastbank Esplanade (Portland Fire & Rescue Station is a good landmark).
The Esplanade is the perfect finale to any Portland biking adventure—riverfront views and unobstructed daylight right till the sun dips past the skyscrapers.