28 days in Oregon Itinerary

28 days in Oregon Itinerary

Created using Inspirock Oregon vacation planner

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

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Portland

— 4 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.
You'll find plenty of places to visit near Portland: Multnomah Falls (in Bridal Veil) and Evergreen Aviation & Space Museum (in McMinnville). Dedicate the 6th (Tue) to wine at some of the top wineries in the area. There's still lots to do: take in nature's colorful creations at Portland Japanese Garden, examine the collection at Oregon Museum of Science and Industry, learn about wildlife with up-close encounters at Oregon Zoo, and look for all kinds of wild species at Volcano Lands - Private Tours.

To find photos, more things to do, traveler tips, and other tourist information, read Portland online sightseeing planner.

Vancouver, Canada to Portland is an approximately 4.5-hour flight. You can also drive; or take a bus. Expect a bit warmer weather when traveling from Vancouver in October: highs in Portland hover around 22°C, while lows dip to 11°C. Wrap up your sightseeing on the 8th (Thu) to allow time to drive to Hood River.

Things to do in Portland

Tours · Wineries · Museums · Parks

Side Trips

Hood River

— 4 nights
The city of Hood River is the seat of Hood River County, Oregon, United States. Explore the numerous day-trip ideas around Hood River: Bonneville Lock & Dam (in Cascade Locks) and Timberline Lodge and Ski Area (in Timberline Lodge). And it doesn't end there: stroll through Columbia River Gorge National Scenic Area, snap pictures at Bridge of the Gods, learn about winemaking at Marchesi Vineyards, and trek along Historic Columbia River Highway State Trail.

For traveler tips, maps, other places to visit, and other tourist information, read our Hood River trip itinerary builder tool.

Drive from Portland to Hood River in 1.5 hours. Alternatively, you can take a bus; or take a train. Expect a daytime high around 22°C in October, and nighttime lows around 8°C. Finish your sightseeing early on the 12th (Mon) to allow enough time to fly to Bend.

Things to do in Hood River

Parks · Nature · Wildlife · Outdoors

Side Trips

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.
Get out of town with these interesting Bend side-trips: Smith Rock State Park (in Redmond), Sisters (Sahalie and Koosah Falls & McKenzie Pass-Santiam Pass loop) and Crescent Moon Ranch (in Terrebonne). The adventure continues: see the interesting displays at High Desert Museum, take in the dramatic scenery at Tumalo Falls, tour the pleasant surroundings at Newberry National Volcanic Monument, and contemplate the waterfront views at Deschutes River.

To see maps, reviews, traveler tips, and tourist information, refer to the Bend itinerary planning app.

Getting from Hood River to Bend by flight takes about 2.5 hours. Other options: drive; or take a bus. Plan for slightly colder temperatures traveling from Hood River in October, with highs in Bend at 19°C and lows at 3°C. Cap off your sightseeing on the 15th (Thu) early enough to go by car to Crater Lake National Park.

Things to do in Bend

Nature · Parks · Museums · Shopping

Side Trips

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.
On the 16th (Fri), explore the wealth of natural beauty at Crater Lake National Park. Get ready for a full day of sightseeing on the next day: take a memorable drive along Rogue-Umpqua Scenic Byway, take your sightseeing to a higher altitude at Watchman Peak, and then cruise along Rim Dr.

For where to stay, other places to visit, ratings, and tourist information, read Crater Lake National Park trip website.

Getting from Bend to Crater Lake National Park by car takes about 2.5 hours. Other options: do a combination of bus and taxi. Expect a bit warmer temperatures when traveling from Bend in October; daily highs in Crater Lake National Park reach 25°C and lows reach 7°C. Finish your sightseeing early on the 17th (Sat) so you can drive to Ashland.

Things to do in Crater Lake National Park

Nature · Parks · Outdoors · Scenic Drive

Side Trip

Ashland

— 2 nights
Ashland is a city in Jackson County, in the State of Oregon. On the 18th (Sun), relax in the rural setting at Rolling Hills Alpacas, catch a live performance at Oregon Shakespeare Festival, and then walk around Lithia Park. Here are some ideas for day two: view the masterpieces at The Glass Forge, kick your exploration up a notch at Rogue Valley ZipLine Adventure, and then explore the activities along Rogue River.

To see where to stay, traveler tips, other places to visit, and other tourist information, refer to the Ashland tour itinerary planning website.

Traveling by car from Crater Lake National Park to Ashland takes 2 hours. Alternatively, you can do a combination of taxi and bus. In October in Ashland, expect temperatures between 25°C during the day and 7°C at night. Finish up your sightseeing early on the 19th (Mon) so you can go by car to Eugene.

Things to do in Ashland

Wineries · Parks · Tours · Adventure

Side Trips

Eugene

— 2 nights
Eugene is a city of the Pacific Northwest located in the U.S. state of Oregon. Kick off your visit on the 20th (Tue): let the river carry you with Helfrich River Outfitters, then trek along McKenzie River National Recreation Trail, and then contemplate the long history of The Office Bridge. Get ready for a full day of sightseeing on the next day: relax in the rural setting at Bush's Fern View Farms, tour the pleasant surroundings at Cascades Raptor Center, and then indulge your senses at Cork and Barrel - Tours.

To see other places to visit, photos, more things to do, and more tourist information, read Eugene trip planner.

Getting from Ashland to Eugene by car takes about 3.5 hours. Other options: take a bus; or do a combination of bus and train. When traveling from Ashland in October, plan for slightly colder days and about the same nights in Eugene: temperatures range from 22°C by day to 8°C at night. Finish your sightseeing early on the 21st (Wed) so you can drive to Florence.

Things to do in Eugene

Wildlife · Parks · Tours · Outdoors

Side Trips

Florence

— 2 nights
Florence is a coastal city in Lane County, in the U.S. state of Oregon. On the 22nd (Thu), get great views at Strawberry Hill Wayside, then cruise along Cape Perpetua Visitor Center - Siuslaw National Forest, then take in the dramatic natural features at Thor's Well, and finally explore the striking landscape at Devil's Churn. Here are some ideas for day two: explore the fascinating underground world of Sea Lion Caves, cruise along Oregon Coast Hwy, then see the interesting displays at Given Back Bird Houses Working Museum, and finally visit a coastal fixture at Heceta Head Lighthouse.

To find reviews, other places to visit, traveler tips, and other tourist information, go to the Florence trip itinerary app.

Getting from Eugene to Florence by car takes about 1.5 hours. Other options: take a bus. In October in Florence, expect temperatures between 20°C during the day and 11°C at night. Finish your sightseeing early on the 23rd (Fri) so you can drive to Newport.

Things to do in Florence

Nature · Parks · Scenic Drive · Outdoors

Side Trips

Newport

— 3 nights
A town that survives on the sea, Newport's population of just over 10,000 supports a healthy commercial fishing industry.
Explore the numerous day-trip ideas around Newport: Yachats coastline (in Yachats) and Lincoln City Glass Center (in Lincoln City). There's still lots to do: stroll through Yaquina Head Outstanding Natural Area, stop by Ainslee's Salt Water Taffy, walk around Whale Park, and kick back and relax at Fogarty Creek State Recreation Area.

To see ratings, more things to do, photos, and more tourist information, go to the Newport trip planner.

You can drive from Florence to Newport in 1.5 hours. Alternatively, you can take a bus. In October, daytime highs in Newport are 18°C, while nighttime lows are 10°C. Finish your sightseeing early on the 26th (Mon) to allow enough time to drive to Tillamook.

Things to do in Newport

Parks · Museums · Wildlife · Beaches

Side Trips

Tillamook

— 2 nights
The city of Tillamook is the county seat of Tillamook County, Oregon, United States. On the 27th (Tue), immerse yourself in nature at Nehalem Bay State Park, then admire the majestic nature at Oswald West State Park, and then go for a stroll along the water at Kelly's Brighton Marina. Get ready for a full day of sightseeing on the next day: take a memorable drive along Three Capes Scenic Drive, then contemplate the long history of Tillamook Air Museum, and then tour the pleasant surroundings at Kilchis Point Reserve.

To find other places to visit, reviews, and more tourist information, go to the Tillamook day trip site.

Traveling by car from Newport to Tillamook takes 2 hours. Alternatively, you can take a bus. The time zone difference moving from Pacific Standard Time to Mountain Standard Time is 1 hour. In October, plan for daily highs up to 20°C, and evening lows to 8°C. Finish your sightseeing early on the 28th (Wed) so you can drive to Astoria.

Things to do in Tillamook

Parks · Nature · Wildlife · Museums

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.
Get out of town with these interesting Astoria side-trips: Cannon Beach (Hug Point State Park, Haystack Rock, &more). Spend the 31st (Sat) exploring nature at Fort Clatsop National Memorial. Next up on the itinerary: admire all the interesting features of Astoria Column, see the interesting displays at Seaside Inverted Experience, immerse yourself in nature at Fort Stevens State Park, and pause for some photo ops at Seaside Beach Lewis and Clark Monument.

To see ratings, reviews, traveler tips, and other tourist information, refer to the Astoria road trip site.

Drive from Tillamook to Astoria in 2 hours. Alternatively, you can take a bus. Traveling from Tillamook to Astoria, you'll gain 1 hour due to the time zone difference. October in Astoria sees daily highs of 20°C and lows of 10°C at night. Wrap up your sightseeing on the 31st (Sat) early enough to drive back home.

Things to do in Astoria

Parks · Nature · Historic Sites · Beaches

Side Trips

Oregon travel guide

4.4
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.