31 days in Oregon Itinerary

31 days in Oregon Itinerary

Created using Inspirock Oregon journey planner

Make it your trip
Fly
1
Ashland
— 1 night
Drive
2
Crater Lake National Park
— 2 nights
Drive
3
Bend
— 3 nights
Drive
4
Eugene
— 4 nights
Drive
5
Florence
— 2 nights
Drive
6
Newport
— 2 nights
Drive
7
Tillamook
— 2 nights
Drive
8
Astoria
— 3 nights
Drive
9
Hood River
— 4 nights
Drive
10
Portland
— 6 nights
Fly to Amsterdam Schiphol, Train to Brussels

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Ashland

— 1 night
Ashland is a city in Jackson County, in the State of Oregon. On the 1st (Sat), stop by Rogue Creamery and then relax in the rural setting at Rolling Hills Alpacas. Here are some ideas for day two: walk around Lithia Park, see a show at Oregon Shakespeare Festival, and then relax and float downstream with a rafting and tubing tour.

To find where to stay, reviews, other places to visit, and tourist information, use the Ashland tour itinerary app.

Brussels, Belgium to Ashland is an approximately 17.5-hour flight. The time zone difference when traveling from Brussels to Ashland is minus 9 hours. Expect a bit warmer weather when traveling from Brussels in May: highs in Ashland hover around 29°C, while lows dip to 11°C. Cap off your sightseeing on the 2nd (Sun) early enough to go by car to Crater Lake National Park.

Things to do in Ashland

Parks · Nightlife · Outdoors · Adventure

Side Trip

Crater Lake National Park

— 2 nights
Reaching a depth of 592 m (1,943 ft), Crater Lake is the deepest lake in the United States.
Kick off your visit on the 3rd (Mon): explore the wealth of natural beauty at Crater Lake National Park. Keep things going the next day: trek along Garfield Peak, take in the dramatic scenery at Whitehorse Falls, and then take a peaceful walk through Umpqua National Forest.

To see other places to visit and tourist information, go to the Crater Lake National Park online trip itinerary maker.

Traveling by car from Ashland to Crater Lake National Park takes 2 hours. Alternatively, you can do a combination of bus and taxi. May in Crater Lake National Park sees daily highs of 29°C and lows of 11°C at night. Finish up your sightseeing early on the 4th (Tue) so you can go by car to Bend.

Things to do in Crater Lake National Park

Parks · Nature · Trails · Outdoors

Side Trip

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.
You'll find plenty of places to visit near Bend: Smith Rock State Park (in Redmond), Sisters (Cascade Street Distillery & Sahalie and Koosah Falls) and Crooked River Scenic Drive (in Prineville). There's lots more to do: examine the collection at High Desert Museum, tour the pleasant surroundings at Newberry National Volcanic Monument, see Off-Road Tours, and hike along Lava Cast Forest Trail.

For ratings, photos, and tourist information, use the Bend holiday planner.

Drive from Crater Lake National Park to Bend in 2.5 hours. Alternatively, you can do a combination of taxi and bus. Prepare for little chillier weather when traveling from Crater Lake National Park in May: high temperatures in Bend hover around 22°C and lows are around 5°C. Finish your sightseeing early on the 7th (Fri) to allow enough time to drive to Eugene.

Things to do in Bend

Parks · Nature · Outdoors · Museums

Side Trips

Eugene

— 4 nights
Eugene is a city of the Pacific Northwest located in the U.S. state of Oregon. Venture out of the city with trips to Albany (Childers' Raspberry Farm & The Historic Carousel and Museum), Roseburg (Riversdale Valley Farm & Paul O'Brien Winery) and Wildlife Safari (in Winston). There's lots more to do: stroll around Hendricks Park, relax in the rural setting at Johnson Farms, stop by Down to Earth Home, Garden, & Gift, and gain insight at University of Oregon.

To find more things to do, traveler tips, other places to visit, and other tourist information, use the Eugene online trip itinerary maker.

Drive from Bend to Eugene in 3 hours. Alternatively, you can take a bus. Traveling from Bend in May, Eugene is somewhat warmer at night with lows of 9°C. Finish up your sightseeing early on the 11th (Tue) so you can go by car to Florence.

Things to do in Eugene

Parks · Wildlife · Nature · Breweries & Distilleries

Side Trips

Florence

— 2 nights
Florence is a coastal city in Lane County, in the U.S. state of Oregon. Start off your visit on the 12th (Wed): explore the striking landscape at Thor's Well, take a memorable drive along Cape Perpetua Visitor Center - Siuslaw National Forest, then explore the striking landscape at Devil's Churn, and finally enjoy the sea views from Heceta Head Lighthouse. Here are some ideas for day two: explore the wealth of natural beauty at Oregon Dunes National Recreation Area.

To see photos, reviews, more things to do, and more tourist information, use the Florence visit planner.

Traveling by car from Eugene to Florence takes 1.5 hours. Alternatively, you can take a bus. Traveling from Eugene in May, you will find days in Florence are a bit cooler (19°C), and nights are about the same (11°C). Wrap up your sightseeing on the 13th (Thu) to allow time to drive to Newport.

Things to do in Florence

Nature · Parks · Scenic Drive · Outdoors

Side Trips

Newport

— 2 nights
A town that survives on the sea, Newport's population of just over 10,000 supports a healthy commercial fishing industry.
Start off your visit on the 14th (Fri): get up close and personal with brilliant marine life at Oregon Coast Aquarium, then engage your brain at Hatfield Marine Science Center, and then take in the waterfront at Yachats coastline. Get ready for a full day of sightseeing on the 15th (Sat): visit a coastal fixture at Yaquina Head Lighthouse, look for all kinds of wild species at Yaquina Head Outstanding Natural Area, then view the masterpieces at Lincoln City Glass Center, and finally look for gifts at Ainslee's Salt Water Taffy.

Discover how to plan a Newport trip in just a few steps with Inspirock's itinerary builder.

Traveling by car from Florence to Newport takes 1.5 hours. Alternatively, you can take a bus. In May in Newport, expect temperatures between 17°C during the day and 9°C at night. Finish your sightseeing early on the 15th (Sat) so you can drive to Tillamook.

Things to do in Newport

Parks · Museums · Shopping · Zoos & Aquariums

Side Trips

Tillamook

— 2 nights
The city of Tillamook is the county seat of Tillamook County, Oregon, United States. Kick off your visit on the 16th (Sun): look for gifts at Cloud and Leaf Bookstore, then tour the pleasant surroundings at Manzanita Beach, then admire the majestic nature at Nehalem Bay State Park, and finally stroll through Rockaway Beach Wayside. Keep things going the next day: kick back and relax at Hug Point State Recreation Site, then immerse yourself in nature at Oswald West State Park, and then take a memorable drive along Three Capes Scenic Drive.

To find photos, maps, where to stay, and other tourist information, go to the Tillamook day trip planning tool.

Traveling by car from Newport to Tillamook takes 2 hours. Alternatively, you can take a bus. Traveling from Newport to Tillamook, you'll lose 1 hour due to the time zone difference. In May in Tillamook, expect temperatures between 19°C during the day and 9°C at night. Finish up your sightseeing early on the 17th (Mon) so you can go by car to Astoria.

Things to do in Tillamook

Parks · Outdoors · Beaches · Nature

Side Trips

Astoria

— 3 nights

Spirit of the Columbia

Astoria, named for famed fur trader John Jacob Astor, resides near the mouth of the Columbia River.
Venture out of the city with trips to Cannon Beach (Hug Point State Park, Haystack Rock, &more). And it doesn't end there: explore the wealth of natural beauty at Fort Clatsop National Memorial, don't miss a visit to Seafarers' Park, pause for some photo ops at Astoria Column, and contemplate the long history of Lewis & Clark Salt Works.

To find reviews, other places to visit, ratings, and more tourist information, refer to the Astoria trip tool.

Getting from Tillamook to Astoria by car takes about 2 hours. Other options: take a bus. You'll gain 1 hour traveling from Tillamook to Astoria due to the time zone difference. In May, daily temperatures in Astoria can reach 19°C, while at night they dip to 10°C. Wrap up your sightseeing on the 20th (Thu) to allow time to drive to Hood River.

Things to do in Astoria

Parks · Nature · Historic Sites · Beaches

Side Trips

Hood River

— 4 nights
The city of Hood River is the seat of Hood River County, Oregon, United States. Get out of town with these interesting Hood River side-trips: Bonneville Lock & Dam (in Cascade Locks), Timberline Lodge and Ski Area (in Timberline Lodge) and Kiyokawa Family Orchards (in Parkdale). The adventure continues: contemplate the waterfront views at Columbia River Gorge National Scenic Area, trek along Horsetail Falls- Columbia River Gorge, see the interesting displays at Western Antique Aeroplane & Automobile Museum, and stroll through Historic Columbia River Highway State Trail.

To see where to stay, photos, reviews, and more tourist information, read Hood River trip itinerary planner.

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. May in Hood River sees daily highs of 22°C and lows of 11°C at night. Wrap up your sightseeing on the 24th (Mon) early enough to drive to Portland.

Things to do in Hood River

Parks · Outdoors · Nature · Museums

Side Trips

Portland

— 6 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.
Explore Portland's surroundings by going to Wooden Shoe Tulip Farm (in Woodburn), Multnomah Falls (in Bridal Veil) and Evergreen Aviation & Space Museum (in McMinnville). Dedicate the 29th (Sat) to wine at some of the top wineries in the area. And it doesn't end there: take in nature's colorful creations at Portland Japanese Garden, admire nature's wide array of creatures at Oregon Zoo, see the interesting displays at Oregon Museum of Science and Industry, and stop by Powell's City of Books.

To plan Portland vacation without wasting time, ask Inspirock to design an itinerary.

Getting from Hood River to Portland by car takes about 1.5 hours. Other options: take a bus; or take a train. In May in Portland, expect temperatures between 24°C during the day and 12°C at night. Finish your sightseeing early on the 30th (Sun) to allow enough time to travel back home.

Things to do in Portland

Tours · Parks · Wineries · Museums

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.