If you're coming from out of town, think about spending a few days in Portland! Here are our favorite things:
Restaurants
$1 oyster Happy Hour at Jacqueline, Pho Oregon, Luce, Mole Mole, Rose VL/Ha VL, Yaowarat, Ken's Artisan Pizza, Lovely's 50/50, Screen Door (for breakfast)
Coffee
Heart Coffee, Proud Mary, Albina Press, Coava.
Bars
Angel Face, Expatriate, Hale Pele (tiki bar!), Horse Brass (pub with great fish and chips).
Shops & Entertainment
Little Axe Records (Jed's shop!), Hollywood Theatre (historic movie theatre next to Little Axe!), Powell's Books (giant, famous bookstore), Mississippi Avenue (lots of shops to look into), Nationale (cute book shop/stuff shop/art gallery), Japanese Garden, Lan Su Chinese Garden.
Nature
Walk through Forest Park or Laurelhurst Park, see the roses at Peninsula Park, drive out to the Gorge for a hike, and it's probably still warm enough to swim at a river (Washougal, Sandy) or Sauvie Island!
Dundee is Oregon's wine country, so there are plenty of vineyards to visit. We haven't been to many, but Furiosa Vineyards has a great view and Argyle Winery is an Oregon favorite. Here's a whole list for you: https://wineryhuntoregon.com/best-wineries-dundee-hills-north/
Take a drive out to the coast! There are plenty of beautiful places both north and south, from Cannon Beach to Astoria.