23 days in Oregon Itinerary

23 days in Oregon Itinerary

Created using Inspirock Oregon trip planner

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Route & dates

23 days in Oregon Itinerary

Start: San Francisco
Fly:  4​h 45​min
1
Bend
— 3 nights
Drive:  2​h 45​min
2
Silverton
— 3 nights
Drive:  2​h 45​min
3
Astoria
— 5 nights
Drive:  3​h
4
Hood River
— 4 nights
bus:  1​h 15​min
5
Portland
— 7 nights
Fly:  4​h
End: San Francisco

3
nights
Bend

Bend ©
An old logging town at the crux of the high desert and ponderosa pine forest, Bend melds a love of the outdoors with cosmopolitan flair.
Your cultural itinerary includes sights like High Desert Museum and The Office Bridge. Escape the urban bustle at Smith Rock State Park and John Day Fossil Beds National Monument, Painted Hills Unit. Explore the numerous day-trip ideas around Bend: Willamette Mountain Mercantile-Oakridge Bike Shop (in Oakridge) and Erickson Aircraft Collection (in Madras). There's much more to do: take a peaceful walk through Deschutes National Forest, wander the streets of City of Sisters, and take in the dramatic natural features at Balancing Rocks.

For more things to do, photos, other places to visit, and tourist information, you can read our Bend itinerary builder website .

San Francisco to Bend is an approximately 5-hour combination of flight and bus. You can also do a combination of subway, flight, and bus; or drive. Traveling from San Francisco in April, expect Bend to be a bit cooler, temps between 58°F and 33°F. Wrap up your sightseeing on the 3rd (Fri) early enough to travel to Silverton.

Things to do in Bend

Parks Nature Museums

Side Trips

City of Sisters, John Day Fossil Beds National Monument, Painted Hills Unit, Willamette Mountain Mercantile-Oakridge Bike Shop, Erickson Aircraft Collection, Smith Rock State Park
Highlights from your plan
Smith Rock State Park ©
Smith Rock State Park
High Desert Museum ©
High Desert Museum
Deschutes National  Forest ©
Deschutes National Forest

3
nights
Silverton

Silverton ©
Silverton is a city in Marion County, Oregon, United States. Sokol Blosser Winery and St. Mary's Catholic Church are good opportunities to explore the local culture. Popular historic sites such as Mount Angel Abbey and Oregon Garden are in your itinerary. Change things up with these side-trips from Silverton: Amity (Brooks Wine & Keeler Estate Vineyard), Remy Wines (in McMinnville) and Bella Vida Vineyard (in Dundee). There's still lots to do: get engrossed in the history at Powerland Heritage Park, take in the architecture and atmosphere at Queen of Angels Monastery, and do a tasting at K&M Wines.

To find photos, reviews, other places to visit, and more tourist information, use the Silverton road trip planning website .

Traveling by car from Bend to Silverton takes 2.5 hours. Expect somewhat warmer evenings in Silverton when traveling from Bend in May, with lows around 48°F. Wrap up your sightseeing on the 6th (Mon) to allow time to travel to Astoria.

Things to do in Silverton

Wineries Historic Sites Parks

Side Trips

Mount Angel, Dundee, Amity, Carlton, Dayton
Highlights from your plan
Sokol Blosser Winery ©
Sokol Blosser Winery
Keeler Estate Vineyard ©
Keeler Estate Vineyard
Mount Angel Abbey ©
Mount Angel Abbey

5
nights
Astoria

Astoria ©
Astoria, named for famed fur trader John Jacob Astor, resides near the mouth of the Columbia River.
Get in touch with nature at Haystack Rock and Columbia River Maritime Museum. Museum-lovers will appreciate Tillamook Air Museum and Garibaldi Museum. You'll find plenty of places to visit near Astoria: Cannon Beach (Cannon Beach, Ecola State Park, & more), Manzanita Beach (in Manzanita) and Hug Point State Recreation Site (in Arch Cape). Spend the 8th (Wed) exploring nature at Fort Clatsop National Memorial. There's much more to do: look for all kinds of wild species at Astoria Column, get engrossed in the history at Seaside Museum & Historical Society, and examine the collection at Flavel House Museum.

For photos and other tourist information, use the Astoria trip builder tool .

You can drive from Silverton to Astoria in 3 hours. When traveling from Silverton in May, plan for slightly colder days in Astoria, with highs around 62°F, while nights are about the same with lows around 48°F. Finish your sightseeing early on the 11th (Sat) to allow enough time to drive to Hood River.

Things to do in Astoria

Parks Nature Outdoors

Side Trips

Cannon Beach, Seaside Museum & Historical Society, Hug Point State Recreation Site, Tillamook Air Museum, Manzanita Beach
Highlights from your plan
Fort Clatsop National Memorial ©
Fort Clatsop National Memorial
Haystack Rock ©
Haystack Rock
Cannon Beach ©
Cannon Beach

4
nights
Hood River

Hood River ©
The city of Hood River is the seat of Hood River County, Oregon, United States. Get in touch with nature at Timberline Lodge and Ski Area and Rowena Crest Viewpoint. Do some cultural sightseeing at Western Antique Aeroplane & Automobile Museum and Sunshine Mill Winery. Venture out of the city with trips to The Dalles (Old St. Peter's Landmark, The Dalles Murals, & more) and Multnomah Falls (in Bridal Veil). There's still lots to do: explore the activities along Columbia River Gorge National Scenic Area, examine the collection at Columbia Gorge Discovery Center & Museum, take an in-depth tour of Fort Dalles Museum and Anderson Homestead, and trek along Historic Columbia River Highway State Trail.

To find more things to do, ratings, other places to visit, and other tourist information, read our Hood River trip maker site .

Traveling by car from Astoria to Hood River takes 3 hours. Alternatively, you can take a bus; or do a combination of bus and train. In May, plan for daily highs up to 67°F, and evening lows to 49°F. Wrap up your sightseeing on the 15th (Wed) to allow time to drive to Portland.

Things to do in Hood River

Parks Nature Wildlife

Side Trips

The Dalles, Mosier, Multnomah Falls, Timberline Lodge and Ski Area, Columbia River Gorge National Scenic Area
Highlights from your plan
Timberline Lodge and Ski Area ©
Timberline Lodge and Ski Area
Multnomah Falls ©
Multnomah Falls

7
nights
Portland

Portland ©
A big city with a small-town feel, Portland is home to the country's biggest rose test garden, perched on a hill overlooking downtown.
Get in touch with nature at The Grotto - National Sanctuary of Our Sorrowful Mother and Crown Point State Scenic Corridor. Deepen your sense of the past at sights like Pittock Mansion and Columbia River Highway. Explore Portland's surroundings by going to Newberg (Trisaetum Winery and Vineyards, Adelsheim Vineyard, & more), Carlton Winemakers Studio (in Carlton) and Evergreen Aviation & Space Museum (in McMinnville). There's lots more to do: stop by Powell's City of Books, browse the eclectic array of goods at Portland Saturday Market, examine the collection at Oregon Museum of Science and Industry, and view the masterpieces at Live Laugh Love Art.

To see maps, ratings, and more tourist information, refer to the Portland vacation maker app .

Traveling by car from Hood River to Portland takes 1.5 hours. Alternatively, you can take a bus; or take a train. May in Portland sees daily highs of 70°F and lows of 51°F at night. Wrap up your sightseeing by early afternoon on the 22nd (Wed) to allow time for travel back home.

Things to do in Portland

Museums Historic Sites Shopping

Side Trips

Newberg, Columbia River Highway, Evergreen Aviation & Space Museum, Crown Point State Scenic Corridor, Live Laugh Love Art
Highlights from your plan
Powell's City of Books ©
Powell's City of Books
Evergreen Aviation & Space Museum ©
Evergreen Aviation & Space Museum
Columbia River Highway ©
Columbia River Highway

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