Where to Go in Oregon
Mountain Ski
Columbia River Gorge (OR side)
The Columbia River Gorge is a breathtaking 80-mile chasm where towering basalt cliffs rise dramatically from a powerful river, creating one of the Pacific Northwest's most iconic landscapes. Waterfall
11 itineraries
National Park
Crater Lake NP (Rim Village off-season)
Crater Lake in winter is a hushed, ethereal realm where one of America's deepest and most pristine alpine lakes lies cradled in snow-laden peaks. The off-season transforms Rim Village into an intimate
7 itineraries
Mountain Ski
Smith Rock SP (Terrebonne)
Smith Rock State Park stands as a mecca for rock climbers and outdoor enthusiasts, where golden-hued cliffs rise dramatically above the gentle Crooked River in central Oregon's high desert. The park's
11 itineraries
National Park
Silver Falls SP (near Salem)
Silver Falls State Park stands as Oregon's crown jewel for waterfall enthusiasts, where a magnificent loop trail unveils ten cascading falls hidden within old-growth forest and moss-draped canyons. Th
11 itineraries
Mountain Ski
Wallowas (Joseph, Enterprise)
Tucked into Oregon's northeastern corner, the Wallowas offer a rare blend of rugged alpine wilderness and small-town charm that feels genuinely removed from the modern world. Joseph and Enterprise anc
12 itineraries
National Park
John Day Fossil Beds NM (Sheep Rock, Painted Hills, Clarno)
Step into a living geological storybook at John Day Fossil Beds, where 44 million years of Earth's history are painted across impossibly colorful badlands and preserved in ancient stone. Three distinc
8 itineraries
Character City
Eugene area
Nestled in Oregon's Willamette Valley, Eugene is a vibrant college town where natural beauty meets progressive culture. The emerald landscape—lush forests, dramatic waterfalls at Silver Falls State Pa
1 itinerary
Metro
Portland area (day trips)
Portland's day-trip landscape is a study in Pacific Northwest contrasts: lush urban forests give way to dramatic river gorges, while manicured gardens celebrate botanical artistry. Within an hour's dr
5 itineraries
Wine Culinary
Medford area (non-Crater Lake)
Nestled in southern Oregon's fertile valley, the Medford area offers a quieter alternative to crowded mountain destinations, where rolling vineyards meet dramatic volcanic geology. The Rogue Valley ha
1 itinerary
Metro
Portland, Oregon
Portland is a city of verdant bridges, independent spirit, and surprising charm nestled where two rivers meet in the Pacific Northwest. Known for its quirky culture, thriving coffee scene, and commitm
5 itineraries
Character City
Eugene, Oregon
Eugene is Oregon's creative heartbeat, a vibrant college town nestled where the McKenzie and Willamette rivers converge at the edge of the Willamette Valley. Known for its progressive culture, lush na
4 itineraries
Wine Culinary
Salem, Oregon
Salem, Oregon's quiet capital, unfolds as a hidden gem in the heart of the Willamette Valley, where the gentle Willamette River winds through a city that balances small-town charm with genuine cultura
3 itineraries
Oregon Itineraries
2 Days · Young Families
Columbia River Gorge (OR side), Oregon
Mist, Moss, and Little Legs: A Family Weekend in the Gorge
4 stops
2 Days · Couples
Silver Falls SP (near Salem), Oregon
Moss, Mist & Two Hearts: A Waterfall Weekend at Silver Falls
6 stops
2 Days · Couples
Smith Rock SP (Terrebonne), Oregon
Golden Rock, Slow Hours: Two Days at Smith Rock
4 stops
3 Days · Active Retirees
Smith Rock SP (Terrebonne), Oregon
Golden Rock, Slow Steps: 3 Days at Smith Rock
5 stops
3 Days · Active Retirees
Columbia River Gorge (OR side), Oregon
Basalt, Mist, and River Light: 3 Days in the Columbia River Gorge
4 stops
2 Days · Couples
John Day Fossil Beds NM (Sheep Rock, Painted Hills, Clarno), Oregon
Painted Silence: Two Days Among Oregon's Ancient Badlands
5 stops
2 Days · Couples
Wallowas (Joseph, Enterprise), Oregon
Granite Peaks & Quiet Water: Two Days in the Wallowas
6 stops
2 Days · Young Families
Wallowas (Joseph, Enterprise), Oregon
Granite Peaks & Pebbled Shores: A Family Weekend in the Wallowas
3 stops
2 Days · Young Families
Crater Lake NP (Rim Village off-season), Oregon
Blue Water, Small Steps: Two Days at Crater Lake with Little Ones
6 stops
3 Days · Active Retirees
Wallowas (Joseph, Enterprise), Oregon
Granite, Water, and Quiet Light: 3 Days in the Wallowas
6 stops
2 Days · Young Families
Smith Rock SP (Terrebonne), Oregon
Golden Rock, Little Feet: Two Easy Days at Smith Rock
4 stops
2 Days · Couples
Crater Lake NP (Rim Village off-season), Oregon
Blue Held Still: Two Spring Days on the Crater's Rim
6 stops