21 days in Oregon Itinerary

21 days in Oregon Itinerary

Created using Inspirock Oregon tour builder

Make it your trip
Fly to Boise, Bus to Baker City
1
Baker City
— 1 night
Drive
2
Bend
— 3 nights
Drive
3
Hood River
— 4 nights
Drive
4
Astoria
— 4 nights
Drive
5
Lincoln City
— 3 nights
Drive
6
Portland
— 5 nights
Fly

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Baker City

— 1 night
Baker City is a city in and the county seat of Baker County, Oregon, United States. Start off your visit on the 2nd (Sun): take an in-depth tour of Baker Heritage Museum, take an in-depth tour of National Historic Oregon Trail Interpretive Center, then grab your bike and head to Baker City Mini-Loop, and finally explore the different monuments and memorials at Chinese Cemetery.

To see reviews, ratings, other places to visit, and tourist information, read our Baker City trip itinerary builder site.

New York City to Baker City is an approximately 14-hour combination of flight and bus. You can also drive; or take a bus. The time zone difference when traveling from New York City to Baker City is minus 3 hours. Expect colder evenings in Baker City when traveling from New York City in August, with lows around 46°F. Cap off your sightseeing on the 2nd (Sun) early enough to travel to Bend.

Things to do in Baker City

Museums · Outdoors · Trails · Parks

Bend

— 3 nights
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.
Museum-lovers will get to explore High Desert Museum and Oregon Observatory. Visiting River Rafting & Tubing and Smith Rock State Park will get you outdoors. Take a break from Bend with a short trip to Dee Wright Observatory in Blue River, about 1h 15 min away. There's much more to do: take a peaceful walk through Deschutes National Forest, explore the activities along Deschutes River, stop by Artists Gallery Sunriver, and stroll around Drake Park.

To see other places to visit, photos, ratings, and tourist information, read Bend trip itinerary planner.

Traveling by car from Baker City to Bend takes 5 hours. Plan for a bit warmer nights when traveling from Baker City in August since evenings lows in Bend dip to 52°F. Finish your sightseeing early on the 5th (Wed) to allow enough time to drive to Hood River.

Things to do in Bend

Museums · Parks · Nature · Childrens Museums

Side Trips

Hood River

— 4 nights
The city of Hood River is the seat of Hood River County, Oregon, United States. Get in touch with nature at Columbia River Gorge National Scenic Area and Mt. Hood National Forest. Museum-lovers will appreciate Western Antique Aeroplane & Automobile Museum and Art on Oak. Explore Hood River's surroundings by going to Timberline Lodge and Ski Area (in Timberline Lodge) and Sherman County Historical Museum (in Moro). There's much more to do: see the interesting displays at Columbia Gorge Discovery Center & Museum, go for a walk through Rowena Crest Viewpoint, trek along Historic Columbia River Highway State Trail, and get outside with Big Winds.

For traveler tips, maps, more things to do, and other tourist information, read our Hood River online trip builder.

Getting from Bend to Hood River by car takes about 3.5 hours. Other options: fly; or take a bus. Traveling from Bend in August, expect somewhat warmer with lows of 60°F in Hood River. Finish your sightseeing early on the 9th (Sun) so you can drive to Astoria.

Things to do in Hood River

Parks · Nature · Museums · Wildlife

Side Trips

Astoria

— 4 nights

Spirit of the Columbia

Astoria, named for famed fur trader John Jacob Astor, resides near the mouth of the Columbia River.
You'll explore and learn at Columbia River Maritime Museum and Seaside Inverted Experience. Fort Clatsop National Memorial and Lewis & Clark Salt Works will appeal to history buffs. Explore Astoria's surroundings by going to Cannon Beach (Haystack Rock, Oswald West State Park, &more) and Hug Point State Recreation Site (in Arch Cape). There's lots more to do: appreciate the history behind Astoria Column, immerse yourself in nature at Fort Stevens State Park, and stop by Beach Books.

To see other places to visit, traveler tips, reviews, and other tourist information, go to the Astoria trip planner.

Traveling by car from Hood River to Astoria takes 3 hours. Alternatively, you can take a bus; or do a combination of train and bus. Plan for slightly colder temperatures traveling from Hood River in August, with highs in Astoria at 71°F and lows at 55°F. Wrap up your sightseeing on the 13th (Thu) early enough to drive to Lincoln City.

Things to do in Astoria

Parks · Nature · Beaches · Outdoors

Side Trips

Lincoln City

— 3 nights
Lincoln City is a city in Lincoln County, Oregon, United States. Escape the urban bustle at Cape Perpetua Visitor Center - Siuslaw National Forest and Yaquina Head Outstanding Natural Area. Give yourself a bit of retail therapy at Lincoln City Glass Center and Freed Gallery. Get out of town with these interesting Lincoln City side-trips: Yaquina Head Lighthouse (in Newport), Earthworks Gallery (in Yachats) and Tillamook (Tillamook Air Museum & Cape Meares Lighthouse). There's lots more to do: get a taste of the local shopping with Alderhouse Glass Blowers, stroll around Whale Park, take an in-depth tour of Prehistoric, and take in the exciting artwork at Rock Your World: Pacific Northwest Gem & Jewelry Gallery.

To see other places to visit, where to stay, traveler tips, and more tourist information, go to the Lincoln City attractions planner.

Drive from Astoria to Lincoln City in 3 hours. Alternatively, you can take a bus. While traveling from Astoria, expect slightly colder days and about the same nights in Lincoln City, ranging from highs of 64°F to lows of 51°F. Cap off your sightseeing on the 16th (Sun) early enough to go by car to Portland.

Things to do in Lincoln City

Museums · Historic Sites · Shopping · Parks

Side Trips

Portland

— 5 nights

City of Roses

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.
Museum-lovers will appreciate Evergreen Aviation & Space Museum and Portland Art Museum. Step out of the city life by going to Multnomah Falls and Oneonta Gorge. Step out of Portland with an excursion to Willamette Valley Vineyards Wine Center in McMinnville--about 56 minutes away. There's lots more to do: look for gifts at Powell's City of Books, explore the engaging exhibits at Portland Children's Museum, steep yourself in history at Columbia River Highway, and examine the collection at Oregon Museum of Science and Industry.

To see more things to do, photos, other places to visit, and more tourist information, refer to the Portland online trip planner.

Getting from Lincoln City to Portland by car takes about 2 hours. Other options: take a bus. Traveling from Lincoln City in August, you will find days in Portland are much warmer (85°F), and nights are a bit warmer (60°F). You will have some time to spend on the 21st (Fri) before leaving for home.

Things to do in Portland

Museums · Parks · Historic Sites · Shopping

Side Trips

Oregon travel guide

4.5
Gardens · State Parks · Specialty Museums
A land of many faces, Oregon is at once a state of rugged rocky coastlines and deep forests, as well as vibrant cities and small towns packed with award-winning restaurants and trendy shops. With nearly half of its land covered by dense fir, redwood, and pine forests, the state protects varied plant and animal life inside three national parks. In addition to pristine waterfalls, beaches, and lakes perfect for a holiday in nature, Oregon also offers numerous urban tourist attractions. Portland, the state's largest metropolis, notably includes more breweries than any other city in the world, and its central location makes it an ideal base for day trips to Oregon's emerging wine region and many parks.