Larch Mountain (14 miler in the Gorge, 7 miles up & reverse, start at Multnomah Falls):
Angel's Rest to Devil's Rest (12 miler in the Gorge):
Eagle Creek to Tunnel Falls (12 miler in the Gorge):
Gayles Creek (Tillmook Forest 6 mile trail run):
Council Crest (4 miles in the city):
Lewis River (14 miler in SW Washington):
Twin Lakes to Frog Lake (8 mile loop near Mt Hood):
White River (3 snowy miles, base of Mt Hood):
Palmeer Pt/Barlow Road Loop (6 snowy miles near Mt Hood):
I feel incredibly fortunate to live where I do and to have the ability to manipulate my schedule at times to allow for us to get up to a trail head midweek. (Although what I typically don't mention is that I do a lot of prepping & grading on weekends....and that Roxi is a bit of an aggressor sometimes so we prefer weekdays when it's less likely to have lots of extra people/dogs on trail to deal with :))
I get a lot of requests from friends or people new to Portland looking for a decent hike to go on, and truthfully I have several main standbys but I also frequently use a variety of backpacking/trail books and oregonhikers.org to find new options. If you want Gorge specific hikes, look here. If you want Mt. Hood specific hikes, here. I've used the site for five years now and while not all the descriptions are always 100% on point, it's still been an incredible resource. The site used to be more Portland specific, but I've been glad to see it branching out to the entire state of Oregon, as there is SO much more to the state besides just this area. (Can you tell I'm originally from a smaller town in Oregon?!) :)
My standby trails without a doubt are: Gayles Creek & Wilson River Trails in Tillamook Forest, as they're the closest lengthy forest trails to me. Forest Park's trails are technically 10 minutes closer but they're heavily traveled by people these days (although they're great for trail running)....
In the fall I typically hit up Eagle Creek once, also heavily popular (although less so in fall) and a major backpacking trail in summer. Once a summer and at least once a winter, I travel the Twin Lakes loop. At least once a winter I also do White River, but if you go on the weekend it's a challenge to bypass the families that are having a fun time sledding here too. Once a year, I also tend to do one of the Multnomah Falls options. The rest of the time I try to find something new in SW Washington, the Gorge, or near Mt Hood...unless I have the time & money to make a trek over to Central (3-4 hours away) or Southern Oregon (4+ hours) :) Not all trails are always well signed (it's a good idea to have an actual trail map from a store like REI) and I'm not going to lie, even with the trail "skills" and numerous miles on trail that I have I can't count the number of times I've lost the next leg of the trail (downed trees, snowed over, darkness, overgrown trails, etc) and had to contemplate backtracking before being able to navigate my way on. Next major purchase once I have some debts paid off might just be an expensive GPS system to load maps on....
But altogether, always stoked to get us to a trail head and to start venturing onto a trail. Here's hoping we can get weekly or every other week hikes in this term!