35 days in Oregon Itinerary

35 days in Oregon Itinerary

Created using Inspirock Oregon attractions planner

Plan created by another user. Make it yours
1
Portland
— 4 nights
2
Astoria
— 2 nights
3
McMinnville
— 3 nights
4
Lincoln City
— 2 nights
5
Florence
— 1 night
6
Bandon
— 2 nights
7
Gold Beach
— 2 nights
8
Brookings
— 4 nights
9
Grants Pass
— 2 nights
10
Prospect
— 2 nights
11
Bend
— 5 nights
12
Hood River
— 4 nights

4
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.
Escape the urban bustle at Waterfront Renaissance Trail and Steigerwald Lake National Wildlife Refuge. Let the collections at Rice NW Museum of Rocks and Minerals and Oregon Jewish Museum and Center For Holocaust Education capture your imagination. Explore Portland's surroundings by going to The Chehalis Centralia Railroad & Museum (in Chehalis) and Ardiri Winery and Vineyards (in Cornelius). There's much more to do: visit Multnomah Village, get engrossed in the history at Wells Fargo Museum, take in the views from Tilikum Crossing, and wander the streets of Northwest (Nob Hill).

To find maps, reviews, ratings, and tourist information, go to the Portland trip planner.

Orlando to Portland is an approximately 9-hour flight. You can also drive; or do a combination of bus and train. Due to the time zone difference, you'll gain 3 hours traveling from Orlando to Portland. Traveling from Orlando in May, things will get little chillier in Portland: highs are around 70°F and lows about 51°F. Finish your sightseeing early on the 19th (Tue) to allow enough time to drive to Astoria.

Things to do in Portland

Parks · Museums · Wildlife

Side Trips

Steigerwald Lake National Wildlife Refuge, Waterfront Renaissance Trail, The Chehalis Centralia Railroad & Museum, Hyland Forest Park, Rice NW Museum of Rocks and Minerals
Highlights from your plan
Rice NW Museum of Rocks and Minerals ©
Rice NW Museum of Rocks and Minerals
Multnomah Village ©
Multnomah Village
The Chehalis Centralia Railroad & Museum ©
The Chehalis Centralia Railroad & Museum

2
nights
Astoria

Astoria ©
Astoria, named for famed fur trader John Jacob Astor, resides near the mouth of the Columbia River.
Start off your visit on the 20th (Wed): immerse yourself in nature at Oswald West State Park, then examine the collection at Heritage Museum, and then learn about winemaking at Shallon Winery. Keep things going the next day: stroll through The Lewis And Clark National And State Historical Parks and then see the interesting displays at Flavel House Museum.

For photos, where to stay, traveler tips, and more tourist information, you can read our Astoria online driving holiday planner.

Drive from Portland to Astoria in 2 hours. Alternatively, you can take a bus. While traveling from Portland, expect a bit cooler days and about the same nights in Astoria, ranging from highs of 62°F to lows of 48°F. Finish up your sightseeing early on the 21st (Thu) so you can go by car to McMinnville.

Things to do in Astoria

Parks · Nature · Museums

Side Trip

Oswald West State Park
Highlights from your plan
Oswald West State Park ©
Oswald West State Park
Flavel House Museum ©
Flavel House Museum

3
nights
McMinnville

McMinnville ©
McMinnville is the county seat and largest city of Yamhill County, Oregon, United States. Keep things going the next day: learn about winemaking at Eyrie Vineyards, learn about winemaking at Remy Wines, do a tasting at R Stuart & Co., then learn about winemaking at Elizabeth Chambers Cellar, and finally do a tasting at Willamette Valley Vineyards Wine Center.

To find other places to visit, reviews, photos, and other tourist information, go to the McMinnville itinerary builder website.

You can drive from Astoria to McMinnville in 3 hours. Alternatively, you can do a combination of bus and tram; or take a bus. Traveling from Astoria in May, expect nights in McMinnville to be about the same, around 47°F, while days are a bit warmer, around 70°F. Wrap up your sightseeing on the 24th (Sun) to allow time to drive to Lincoln City.

Things to do in McMinnville

Wineries · Museums

Side Trips

Dayton, Powerland Heritage Park, Brooks Wine
Highlights from your plan
Eyrie Vineyards ©
Eyrie Vineyards
Powerland Heritage Park ©
Powerland Heritage Park
Vista Hills Treehouse Tasting Room ©
Vista Hills Treehouse Tasting Room

2
nights
Lincoln City

Lincoln City ©
Lincoln City is a city in Lincoln County, Oregon, United States. Kick off your visit on the 24th (Sun): snap pictures at Drift Creek Covered Bridge, take in the exciting artwork at Artists's Co-op Gallery, take an in-depth tour of Prehistoric, view the masterpieces at Rock Your World: Pacific Northwest Gem & Jewelry Gallery, then view the masterpieces at Freed Gallery, and finally take in the exciting artwork at Mossy Creek Pottery. Get ready for a full day of sightseeing on the 25th (Mon): walk around Siletz Bay Park, then relax in the rural setting at Barking Dog Farm, then enjoy the sand and surf at Taft Bay, and finally enjoy the sand and surf at Fogarty Creek State Recreation Area.

For maps, ratings, traveler tips, and more tourist information, refer to the Lincoln City online journey planner.

Traveling by car from McMinnville to Lincoln City takes 1.5 hours. Alternatively, you can take a bus. While traveling from McMinnville, expect a bit cooler days and about the same nights in Lincoln City, ranging from highs of 58°F to lows of 46°F. Finish your sightseeing early on the 26th (Tue) to allow enough time to drive to Florence.

Things to do in Lincoln City

Parks · Museums · Shopping

Side Trip

Fogarty Creek State Recreation Area
Highlights from your plan
Mossy Creek Pottery ©
Mossy Creek Pottery
Fogarty Creek State Recreation Area ©
Fogarty Creek State Recreation Area
Artists's Co-op Gallery ©
Artists's Co-op Gallery

1
night
Florence

Florence ©
Florence is a coastal city in Lane County, in the U.S. Kick off your visit on the 26th (Tue): kick back and relax at Heceta Beach, then play a few rounds at Ocean Dunes Golf Links, and then stroll through Hobbit Trail.

For maps, other places to visit, and tourist information, go to the Florence trip planner.

Traveling by car from Lincoln City to Florence takes 2 hours. Alternatively, you can take a bus. May in Florence sees daily highs of 62°F and lows of 49°F at night. Finish up your sightseeing early on the 27th (Wed) so you can go by car to Bandon.

Things to do in Florence

Outdoors · Parks · Golf
Highlights from your plan
Ocean Dunes Golf Links ©
Ocean Dunes Golf Links
Heceta Beach ©
Heceta Beach

2
nights
Bandon

Bandon ©
Bandon is a city in Coos County, Oregon, United States, on the south side of the mouth of the Coquille River. On the 27th (Wed), admire the majestic nature at Port Orford Heads State Park, then see the interesting displays at Port Orford Lifeboat Station Museum, then stop by Misty Meadows Jams, and finally enjoy the sand and surf at Bandon State Park. On the 28th (Thu), you'll have a packed day of sightseeing: hike along South Slough National Estuarine Research Reserve, tee off at Pacific Dunes, and then enjoy the sand and surf at Coquille Point.

For where to stay, more things to do, photos, and other tourist information, use the Bandon trip planner.

You can drive from Florence to Bandon in 1.5 hours. Alternatively, you can take a bus. In May, daily temperatures in Bandon can reach 62°F, while at night they dip to 49°F. Finish your sightseeing early on the 29th (Fri) to allow enough time to drive to Gold Beach.

Things to do in Bandon

Outdoors · Parks · Nature

Side Trips

Port Orford, South Slough National Estuarine Research Reserve
Highlights from your plan
Bandon State Park ©
Bandon State Park
Port Orford Lifeboat Station Museum ©
Port Orford Lifeboat Station Museum

2
nights
Gold Beach

Gold Beach ©
Gold Beach is a city in and the county seat of Curry County, Oregon, United States, on the Oregon Coast. On the 29th (Fri), examine the collection at Curry Historical Museum, stop by Gold Beach Books, then enjoy the sand and surf at Ophir Beach, and finally tour the pleasant surroundings at Myers Creek Beach. On the next day, contemplate the waterfront views at Illinois River and then tee off at Cedar Bend Golf Club.

To see photos, other places to visit, reviews, and other tourist information, you can read our Gold Beach trip planner.

You can drive from Bandon to Gold Beach in 1.5 hours. Another option is to take a bus. Expect a daytime high around 63°F in May, and nighttime lows around 48°F. Cap off your sightseeing on the 31st (Sun) early enough to go by car to Brookings.

Things to do in Gold Beach

Outdoors · Parks · Beaches

Side Trips

Myers Creek Beach, Ophir Beach
Highlights from your plan
Ophir Beach ©
Ophir Beach
Curry Historical  Museum ©
Curry Historical Museum
Cedar Bend Golf Club ©
Cedar Bend Golf Club

4
nights
Brookings

Brookings ©
Brookings is a city in Curry County, Oregon, United States. Get in touch with nature at Samuel H. Boardman State Scenic Corridor and Enderts Beach. Your cultural itinerary includes sights like End of the Trail Museum and Del Norte County History Museum. You'll find plenty of places to visit near Brookings: Crescent City (Point St George Park & Northcoast Marine Mammal Center). There's much more to do: kick back and relax at Lone Ranch Beach, take some stellar pictures from Natural Bridges Viewpoint, admire the majestic nature at McVay Rock State Recreation Site, and trek along Oregon Redwood Trail.

For traveler tips, reviews, and other tourist information, use the Brookings holiday planner.

Getting from Gold Beach to Brookings by car takes about an hour. In May in Brookings, expect temperatures between 63°F during the day and 48°F at night. Wrap up your sightseeing on the 4th (Thu) to allow time to drive to Grants Pass.

Things to do in Brookings

Parks · Outdoors · Beaches

Side Trips

Crescent City, End of the Trail Museum, Enderts Beach
Highlights from your plan
Samuel H. Boardman State Scenic Corridor ©
Samuel H. Boardman State Scenic Corridor
Lone Ranch Beach ©
Lone Ranch Beach
Enderts Beach ©
Enderts Beach

2
nights
Grants Pass

Grants Pass ©
Grants Pass is a city in, and the county seat of, Josephine County, Oregon, United States. Start off your visit on the 4th (Thu): do a tasting at Wooldridge Creek Winery, then explore the different monuments and memorials at Jacksonville Cemetery, then learn about winemaking at Troon Vineyard, and finally walk around Schroeder County Park. Here are some ideas for day two: relax in the rural setting at Rogue Creamery Dairy Farm, admire the masterpieces at Grants Pass Museum of Art, see the interesting displays at Schmidt House Museum, then examine the collection at Bear Hotel Artworks Museum, then pause for some photo ops at Grants Pass Caveman, and finally look for gifts at The Kitchen Company.

For reviews, traveler tips, more things to do, and more tourist information, you can read our Grants Pass day trip planning website.

You can drive from Brookings to Grants Pass in 2 hours. June in Grants Pass sees daily highs of 70°F and lows of 49°F at night. Finish up your sightseeing early on the 6th (Sat) so you can go by car to Prospect.

Things to do in Grants Pass

Museums · Wineries · Parks

Side Trip

Jacksonville Cemetery
Highlights from your plan
Grants Pass Museum of Art ©
Grants Pass Museum of Art
Schmidt House Museum ©
Schmidt House Museum
Wooldridge Creek Winery ©
Wooldridge Creek Winery

2
nights
Prospect

Prospect ©
Prospect is an unincorporated community in Jackson County, in the U.S. Start off your visit on the 6th (Sat): take in the dramatic scenery at Plaikni Falls, hike along Watchman Peak, then tour the pleasant surroundings at Pinnacles Trail, and finally hike along Castle Crest Wildflower Trail. Get ready for a full day of sightseeing on the next day: get great views at Natural Bridge Viewpoint, hike along Annie Creek Canyon, and then hike along Mount Scott.

To see ratings, photos, and tourist information, refer to the Prospect trip builder tool.

Getting from Grants Pass to Prospect by car takes about 1.5 hours. Prepare for a bit warmer weather when traveling from Grants Pass in June: high temperatures in Prospect hover around 86°F and lows are around 55°F. Finish your sightseeing early on the 8th (Mon) so you can travel to Bend.

Things to do in Prospect

Parks · Outdoors · Trails

Side Trip

Crater Lake National Park
Highlights from your plan
Plaikni Falls ©
Plaikni Falls
Mount Scott ©
Mount Scott
Watchman Peak ©
Watchman Peak

5
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.
Dee Wright Observatory and The Museum at Warm Springs will appeal to museum buffs. Get outdoors at Deschutes River Trail and Peterson Ridge Trail. Get out of town with these interesting Bend side-trips: Erickson Aircraft Collection (in Madras), City of Sisters (in Sisters) and Tumalo Mountain (in Redmond). Next up on the itinerary: sample the tasty concoctions at Deschutes Brewery, take a peaceful walk through Shevlin Park, explore the activities along Little Cultus Lake, and hike along Oregon Badlands Wilderness Trails.

For traveler tips, photos, other places to visit, and other tourist information, you can read our Bend trip planner.

Getting from Prospect to Bend by car takes about 2.5 hours. Expect a bit cooler temperatures when traveling from Prospect in June; daily highs in Bend reach 75°F and lows reach 45°F. Wrap up your sightseeing on the 13th (Sat) to allow time to drive to Hood River.

Things to do in Bend

Parks · Outdoors · Nature

Side Trips

Sisters, Erickson Aircraft Collection, Dee Wright Observatory, Artists Gallery Sunriver, Tumalo Mountain
Highlights from your plan
South Sister ©
South Sister
Dee Wright Observatory ©
Dee Wright Observatory
City of Sisters ©
City of Sisters

4
nights
Hood River

Hood River ©
The city of Hood River is the seat of Hood River County, Oregon, United States. Discover out-of-the-way places like Cathedral Ridge Winery and Presby Museum. Fire Museum in City Hall and Art on Oak will appeal to museum buffs. You'll find plenty of places to visit near Hood River: Stonehenge Memorial (in Goldendale) and Columbia Hills State Park (in Dallesport). The adventure continues: do a tasting at Mt. Hood Winery, walk around Panorama Point County Park, and stroll through Rowena Crest Viewpoint.

For maps, other places to visit, more things to do, and tourist information, you can read our Hood River online tour itinerary planner.

Traveling by car from Bend to Hood River takes 3.5 hours. Alternatively, you can fly; or take a bus. Traveling from Bend in June, Hood River is somewhat warmer at night with lows of 55°F. On the 17th (Wed), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Hood River

Wineries · Parks · Nature

Side Trips

Goldendale, Idiot's Grace, Rowena Crest Viewpoint, Columbia Hills State Park, Starvation Creek State Park
Highlights from your plan
Viento Wines ©
Viento Wines
Mt. Hood Winery ©
Mt. Hood Winery
Cathedral Ridge Winery ©
Cathedral Ridge Winery

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