57 days in Oregon Itinerary

57 days in Oregon Itinerary

Created using Inspirock Oregon trip planner

Make it your trip
Fly
1
Medford
— 3 nights
Drive
2
Eugene
— 6 nights
Drive
3
Bend
— 6 nights
Fly
4
Hood River
— 5 nights
Drive
5
Portland
— 9 nights
Drive
6
Astoria
— 5 nights
Drive
7
Tillamook
— 4 nights
Drive
8
Newport
— 6 nights
Drive
9
Florence
— 4 nights
Drive
10
Bandon
— 4 nights
Drive
11
Brookings
— 4 nights
Drive

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Medford

— 3 nights
Medford is a city in, and county seat of, Jackson County, Oregon, United States. DANCIN Vineyards and Klamath County Museum are good opportunities to explore the local culture. Discover out-of-the-way places like Upper and Lower Table Rock and Rogue Creamery. Change things up with these side-trips from Medford: Red Lily Vineyards (in Jacksonville), Cave Junction (Tiger Preservation Center, Great Cats World Park, &more) and Grants Pass (Riverside Park, The Glass Forge, &more). The adventure continues: trek along Natural Bridge Loop, whizz through the canopy at Rogue Valley ZipLine Adventure, contemplate the waterfront views at Rogue River, and explore the engaging exhibits at ScienceWorks Hands-On Museum.

For more things to do, where to stay, photos, and more tourist information, read Medford trip planner.

San Francisco to Medford is an approximately 4-hour flight. You can also drive. Expect a bit cooler evenings in Medford when traveling from San Francisco in March, with lows around 39°F. Cap off your sightseeing on the 21st (Sun) early enough to travel to Eugene.

Things to do in Medford

Parks · Wineries · Outdoors · Nature

Side Trips

Eugene

— 6 nights
Eugene is a city of the Pacific Northwest located in the U.S. state of Oregon. The Historic Carousel and Museum and Shelton McMurphey Johnson House will appeal to museum buffs. Get some cultural insight at King Estate Winery and Abacela. Change things up with these side-trips from Eugene: Wildlife Safari (in Winston), Roseburg (Stewart Park, Roseburg, Oregon & Watson Falls) and Colliding Rivers Viewpoint (in Glide). And it doesn't end there: trek along Mt Pisgah, stroll through Cascades Raptor Center, explore the landscape on two wheels at Willamette River Trail, and stroll around Skinner Butte Park.

To find photos, ratings, other places to visit, and other tourist information, read our Eugene trip itinerary planner.

Getting from Medford to Eugene by car takes about 3 hours. In March, daily temperatures in Eugene can reach 57°F, while at night they dip to 39°F. Cap off your sightseeing on the 27th (Sat) early enough to go by car to Bend.

Things to do in Eugene

Parks · Wineries · Museums · Shopping

Side Trips

Bend

— 6 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.
Take a break from the city and head to Newberry National Volcanic Monument and Pilot Butte State Scenic Viewpoint. Get a sense of the local culture at Old Mill District and Oregon Observatory. Explore Bend's surroundings by going to Quail Run Golf Course (in La Pine), Salt Creek Falls (in Oakridge) and Sisters (Sahalie and Koosah Falls & City of Sisters). There's lots more to do: delve into the lush surroundings at Deschutes National Forest, immerse yourself in nature at Tumalo State Park, tour the pleasant surroundings at Trail to Benham Falls, and indulge your thirst for a good beer at Deschutes Brewery.

For traveler tips, more things to do, maps, and more tourist information, read our Bend trip builder website.

You can drive from Eugene to Bend in 3 hours. Alternatively, you can take a bus. Traveling from Eugene in March, expect a bit cooler with lows of 31°F in Bend. Cap off your sightseeing on the 2nd (Fri) early enough to catch the flight to Hood River.

Things to do in Bend

Parks · Nature · Outdoors · Tours

Side Trips

Hood River

— 5 nights
The city of Hood River is the seat of Hood River County, Oregon, United States. Satisfy your inner culture vulture at Western Antique Aeroplane & Automobile Museum and Columbia Gorge Discovery Center & Museum. Eschew the tourist crowds and head to Horsetail Falls- Columbia River Gorge and Wahkeena Falls. You'll find plenty of places to visit near Hood River: Bonneville Lock & Dam (in Cascade Locks), Trillium Lake (in Government Camp) and River Rafting & Tubing (in Maupin). Next up on the itinerary: delve into the lush surroundings at Mt. Hood National Forest, stroll through Bonneville Hatchery, admire all the interesting features of Columbia Gorge Scenic Highway, and hit the slopes at Mount Hood.

To find more things to do, photos, reviews, and other tourist information, go to the Hood River road trip website.

Traveling by flight from Bend to Hood River takes 2.5 hours. Alternatively, you can drive; or take a bus. Traveling from Bend in April, expect a bit warmer with lows of 43°F in Hood River. Wrap up your sightseeing on the 7th (Wed) early enough to drive to Portland.

Things to do in Hood River

Parks · Nature · Outdoors · Museums

Side Trips

Portland

— 9 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 explore and learn at Live Laugh Love Art and Portland Children's Museum. Give yourself a bit of retail therapy at Northwest (Nob Hill) and Portland Saturday Market. Explore Portland's surroundings by going to Oneonta Gorge (in Cascade Locks), Portland Women's Forum State Scenic Viewpoint (in Troutdale) and Corbett (Latourell Falls, Vista House, &more). There's lots more to do: do a tasting at Willamette Valley Vineyards, hike along Forest Park, steep yourself in history at Columbia River Highway, and immerse yourself in nature at Tryon Creek State Natural Area.

To see photos, reviews, ratings, and tourist information, use the Portland trip itinerary planning website.

Traveling by car from Hood River to Portland takes 1.5 hours. Alternatively, you can take a bus; or take a train. In April in Portland, expect temperatures between 63°F during the day and 45°F at night. Finish up your sightseeing early on the 16th (Fri) so you can go by car to Astoria.

Things to do in Portland

Parks · Nature · Museums · Outdoors

Side Trips

Astoria

— 5 nights

Spirit of the Columbia

Astoria, named for famed fur trader John Jacob Astor, resides near the mouth of the Columbia River.
Your cultural itinerary includes sights like Fort Clatsop National Memorial and Camp 18 Logging Museum & Restaurant. Museum-lovers will appreciate Flavel House Museum and Icefire Glassworks. Get out of town with these interesting Astoria side-trips: Seaside (Tillamook Head, Seaside Beach, &more) and Cannon Beach (Cannon Beach Gallery, Hug Point State Park, &more). There's still lots to do: appreciate the extensive heritage of The Lewis And Clark National And State Historical Parks, enjoy the sea views from Lightship Columbia, trek along Astoria Oregon Riverwalk, and make a trip to Goonies House.

To see more things to do, reviews, ratings, and tourist information, use the Astoria online trip maker.

You can drive from Portland to Astoria in 2 hours. Another option is to take a bus. Traveling from Portland in April, you will find days in Astoria are slightly colder (58°F), and nights are about the same (43°F). Wrap up your sightseeing on the 21st (Wed) early enough to drive to Tillamook.

Things to do in Astoria

Parks · Historic Sites · Nature · Museums

Side Trips

Tillamook

— 4 nights
The city of Tillamook is the county seat of Tillamook County, Oregon, United States. Escape the urban bustle at Cape Lookout State Park and Manzanita Beach. Your cultural itinerary includes sights like Cape Meares Lighthouse and International Police Museum. Get out of town with these interesting Tillamook side-trips: Nehalem Bay State Park (in Nehalem), Oswald West State Park (in Cannon Beach) and Kelly's Brighton Marina (in Rockaway Beach). The adventure continues: stroll through Rockaway Beach Wayside, trot along with Green Acres Beach & Trail Rides, admire the sheer force of Munson Creek Falls, and take a peaceful walk through Tillamook Forest Center.

Plan a Tillamook trip in moments using our itinerary builder.

Getting from Astoria to Tillamook by car takes about 2 hours. Other options: take a bus. The time zone difference when traveling from Astoria to Tillamook is 1 hour. In April, daytime highs in Tillamook are 58°F, while nighttime lows are 41°F. Cap off your sightseeing on the 25th (Sun) early enough to go by car to Newport.

Things to do in Tillamook

Parks · Nature · Outdoors · Beaches

Side Trips

Newport

— 6 nights
A town that survives on the sea, Newport's population of just over 10,000 supports a healthy commercial fishing industry.
Your itinerary includes some good beach time at Nye Beach and Roads End State Recreation Site. You'll discover tucked-away gems like Yachats coastline and Cape Foulweather. Explore Newport's surroundings by going to Lincoln City (Connie Hansen Garden Conservancy, Prehistoric, &more), Earthworks Gallery (in Yachats) and The Sparks Gallery (in Depoe Bay). The adventure continues: kick back and relax at Fogarty Creek State Recreation Area, immerse yourself in nature at Beverly Beach State Park, make a trip to Boiler Bay State Wayside, and cruise along Otter Crest Loop.

To see photos, reviews, maps, and tourist information, refer to the Newport trip itinerary planning app.

Getting from Tillamook to Newport by car takes about 2 hours. Other options: take a bus. The time zone difference when traveling from Tillamook to Newport is minus 1 hour. In April, daytime highs in Newport are 55°F, while nighttime lows are 42°F. Finish your sightseeing early on the 1st (Sat) so you can drive to Florence.

Things to do in Newport

Parks · Museums · Outdoors · Nature

Side Trips

Florence

— 4 nights
Florence is a coastal city in Lane County, in the U.S. state of Oregon. Get some cultural insight at Umpqua River Lighthouse, Museum,and Gift shop and Oregon Coast. You'll explore the less-touristy side of things at Devil's Churn and Oregon Dunes National Recreation Area. You'll find plenty of places to visit near Florence: Umpqua Triangle Oyster from Aquaculture (in Winchester Bay) and Dean Creek Elk Viewing Area (in Reedsport). The adventure continues: tour the pleasant surroundings at Heceta Beach, take in the views from Siuslaw River Bridge, immerse yourself in nature at Darlingtonia State Natural Site, and play a few rounds at Ocean Dunes Golf Links.

To see photos, more things to do, other places to visit, and tourist information, refer to the Florence day trip website.

You can drive from Newport to Florence in 1.5 hours. Alternatively, you can take a bus. In May, plan for daily highs up to 62°F, and evening lows to 49°F. Finish your sightseeing early on the 5th (Wed) so you can drive to Bandon.

Things to do in Florence

Parks · Nature · Outdoors · Historic Sites

Side Trips

Bandon

— 4 nights
Bandon is a city in Coos County, Oregon, United States, on the south side of the mouth of the Coquille River. Get outdoors at Shore Acres State Park and Betty Kay Charter. Satisfy your inner culture vulture at Cape Blanco Lighthouse and Coquille River Lighthouse. Explore Bandon's surroundings by going to Coos Bay (Cranberry Sweets, Cape Arago State Park, &more) and Port Orford (Humbug Mountain State Park & Cape Blanco State Park). There's lots more to do: explore the striking landscape at Face Rock State Scenic Viewpoint, tour the pleasant surroundings at West Coast Game Park Safari, tee off at Bandon Dunes Golf Resort, and stroll around Bandon South Jetty County Park.

To see ratings and other tourist information, read our Bandon route planner.

Traveling by car from Florence to Bandon takes 1.5 hours. Alternatively, you can take a bus. Expect a daytime high around 62°F in May, and nighttime lows around 49°F. Wrap up your sightseeing on the 9th (Sun) to allow time to travel to Brookings.

Things to do in Bandon

Parks · Nature · Wildlife · Outdoors

Side Trips

Brookings

— 4 nights
Brookings is a city in Curry County, Oregon, United States. Relax by the water at Lone Ranch Beach and Ophir Beach. You'll explore the less-touristy side of things at Harris Beach State Park and Azalea Park. Explore the numerous day-trip ideas around Brookings: Gold Beach (Cedar Bend Golf Club, Geisel Monument State Heritage Site, &more). The adventure continues: immerse yourself in nature at Alfred A Loeb State Park, tour the pleasant surroundings at China Beach, take a memorable drive along Samuel H. Boardman State Scenic Corridor, and enjoy the sand and surf at Myers Creek Beach.

To see reviews, maps, traveler tips, and other tourist information, read our Brookings tour planner.

You can drive from Bandon to Brookings in 2 hours. In May, plan for daily highs up to 63°F, and evening lows to 48°F. Wrap up your sightseeing on the 13th (Thu) early enough to drive back home.

Things to do in Brookings

Outdoors · Parks · Nature · 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.