Start at Water Avenue Coffee (or anywhere near the water. I just like this as a meeting place for easy parking and river access). Go down Salmon Street to the water, a loop from the Tilikum Crossing Bridge to Steel Bridge and back is about 5 miles. This run has all the Portland sights (downtown, river, bridges, markets).
Just after Tilikum, the path goes along the road for a second. Follow signs for the bike lane and it will join back with the separated waterfront trail. If you want longer, continue past Tilikum Bridge and follow signs for Spring Water Corridor. You can take that all the way to the Sellwood bridge, cross the Sellwood and come back the other side. That full loop is about 10 miles.
East PDX Waterfront is ground zero for good food options. Produce Row Cafe and Trifecta Tavern are Portland takes on American gastropub. Afuri and Maruken are two of the best ramen places. There is a food cart pod on 12th, and a bunch of other options stretching out along Hawthorne and Burnside.
Leif Erikson in Forest Park (dirt/gravel fire road)
Leif is the entry-level trail. It’s a fire road closed off to cars, so you get all the beauty of Forest Park (largest urban forest in the country!), without the technical aspects of the single track trails. Though mountain bikes are allowed. The trail runs a net uphill from Northwest District to Germantown Road, but it’s relatively rolling and mild from either direction. I usually do an out and back for 5-8 miles, starting at either end. But there also trails that connect up to Wildwood every few miles, if you want a more adventurous loop.
DragonFly Coffee and Clearing Cafe are two common starting places for group runs to Forest Park. I love DragonFly for the local flair, and their homemade chai latte with hemp milk. But the best coffee in the area is at Groundwork one block over. Or Barista isn’t far.
23rd Avenue is the local shopping street. There you’d find some iconic Portland stores (Tender Loving Empire, The Meadow) and food (Blue Star Donuts, Salt and Straw, Grassa, Pine State Biscuit).
Wildwood Trail (single track trail)
Wildwood is a single track trail that runs the length of Forest Park. It’s almost 30 miles long, and a classic Pacific NW trail run. As you get toward the Northwest District and Pittock Mansion, the trail has a lot of elevation change (I’m a baby with this stuff). To avoid that, I prefer the section from Germantown Road back toward town, there are about 12 miles of relatively flat running.