Wenatchee to Bend
 

Traveling from Wenatchee, WA to Bend, OR in mid- Sept. How many days to spend in Bend: we like to bike, hike & drink beer. We are active retirees with 2 athletic kids.

It depends a bit on where you are going after Bend. There are about 10 craft breweries in Bend and some in Redmond, Sisters and Prineville. Madras is choosing which brewery they want to have in town.
Have you been to Crater Lake NP or the Oregon coast? There are miles of good bike trails in Sunriver. You can also rent kayaks to go on the Deschutes River or one of the lakes along the Cascade Lakes highway
While in Bend be sure to see the High Desert Museum.

Places to stop, visit and/or short detours... Map - https://goo.gl/maps/naPqhcU7WBA2

Wild Horses monument, Vantage WA. This is a marvelous set of statues set on top of a bluff overlooking the Columbia River where I-90 crosses it. Quite moving and well worth the detour.

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Ginkgo Petrified Forest. Across the Columbia from the Wild Horses, this state park is fascinating stop; there are interesting Native American petroglyphs on display at the interpretive center.

St. John's Monastery and Bakery, outside Goldendale WA. A surprising (and surprisingly good) little roadside bakery and cafe out in the middle of nowhere.

Maryhill Stonehenge and Maryhill Museum. The replica of Stonehenge, a World War I memorial built in the belief that the real Stonehenge was a site of human sacrifice, is quite remarkable. The nearby Maryhill Museum is a gem, full of eclectic and fascinating exhibits, ranging from Rodin sculpture to miniature mannequins displaying postwar Parisian fashions (tiny because of fabric shortages) to a world-class collection of Native American arts and crafts.

Hood River and the Hood River Valley. Craft breweries, wineries, galleries, farm-to-table places. The Hood River Valley to the south is spectacular in harvest mode - vineyards, orchards, fruit stands. Drive the "fruit loop" and visit Panorama Point for views of the valley and Mount Hood.

Timberline Lodge. Visit the iconic lodge (used in The Shining) and enjoy the incredible scenery on the side of the big volcano.

Smith Rock State Park. This is quite close to Bend and a marvelous short detour.

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I think 3 would be a good visit, at least if you enjoy beer and are outdoorsy. 1-2 would feel too short.

I don’t know if you already have lodging, but my favorite place to stay is Mcmenamins st Francis.