Theres a few threads covering this. October can still be great, weather wise but it can turn... Halloween at Burnside often seems to be wet.. The Oregon coast is typically less windy that time of year and can be really nice weather in Oct. Lincoln City is an obvious stop and there are some super fun new and older parks nearby. Yachats, Toledo, Bay City, Pacific City. I'd recommend the Salmon River Hike or Cape Lookout hike for some classic Oregon Coast vistas. Further up the coast the parks are a little crustier and not as appealing but Astoria is a great town to visit if you live history and geography...
But from Lincoln City you can turn in land and hit McMinnville, Newberg, Donald, Sherwood, and Tigard on your way into Portland.
Portland, yes Burnside is a mandatory stop... other DIYs include Creston, PSU courts, Feral Cat Cove and some other random little spots here and there. Depends what you like to skate? If it rains, you have Commonwealth and Stronger skateparks...
I'll let other people chime in on food... I'm a Mexican food cart fiend only.... Currently feeling the Breakfast burritos at Habanero burrito on 82nd and Holgate...
Curb spots... find a recently remodeled public school and you'll find a gang of old men standing around talking about how we don't need any more 10' deep bowls...