Portland
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Weekend Getaways

Portland

27 itineraries · Day trips, weekends & long weekends
27 hand-curated itineraries from Portland — active, relaxed, cultural — all within a few hours' drive. Think Timberline & Ramona Falls: Mount Hood's West Side, or Manzanita & Nehalem Bay Wine Country. Real places, real drives, no filler.
🥾 Active
Silver Falls: The Trail of Ten Falls
Oregon's most spectacular waterfall loop begins an hour southeast of Portland — ten named falls in a single 7.2-mile circuit through old-growth Douglas fir, including four you can walk behind. Silver Falls State Park is the largest state park in Oregon and gets overlooked in favor of the Columbia Gorge; that oversight is your advantage on a weekday.
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Pacific NorthwestDay trip
🌿 Relaxed
Dundee Hills Pinot Country
The Dundee Hills are 30 minutes southwest of Portland and constitute one of the great wine landscapes of the American West — volcanic Jory soil, 600-foot hillsides, and Pinot Noir that shocked France in 1979. A day among the established estates and the newer family wineries covers the full range of what the appellation produces, bookended by the Newberg farmers market and a late lunch at the valley floor.
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Pacific NorthwestDay trip
🏛️ Cultural
McMinnville: Wine Country & Aviation History
McMinnville is the capital of Oregon's Pinot Noir country and home to the world's largest display of flying boats — the Evergreen Aviation & Space Museum houses Howard Hughes's Spruce Goose in a building sized around the plane. The town's Third Street galleries and farm-to-table restaurants round out a day that covers more cultural territory than most cities twice its size.
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Pacific NorthwestDay trip