Driving around Parkdale to visit the many Orchards is always fun in the summer. Our two favorites are Kiyokawa Orchards and Mt. View Orchards.
The waterfront park is the best place to watch kite boarders and windsurfers on the Columbia River. Hood River is one of the kite surfing capitals of the world. There are a few breweries just off the park worth visiting, with restaurant and food truck options too.
Move over Willamette Valley AVA - The Columbia River Gorge is the new hot spot for Oregon's wine scene. Ruby and Ian have limited experience visiting wineries in the area but their favorite is Loop de Loop, located in Underwood, Washington. A few others worth checking out are Upsidedown Wine, Analemma, Savage Grace, Hiyu Wine Farm, and Le Doubble Troubble.
There are tons of trailheads enabling easy access to nature. Check out Dog Mountain, Memaloose Hills, Tamanawas Falls, and Umbrella Falls.
Dedicate most of a day to driving up the nine mile access road to reach Tilly Jane and Cloud Cap Inn. It's a special place to us - and to Ian's Aunt Susan and Uncle Jeremy, who were married there! From Tilly Jane, take the 2ish mile hike up to see Eliot Glacier on the Northeastern slopes of Mount Hood. Definitely recommend a car with sturdy suspension if you choose to do it.