35 days in Oregon Itinerary

Created using Inspirock Oregon planner
Make it your trip
Fly
1
Portland
— 4 nights
Drive
2
Astoria
— 2 nights
Drive
3
McMinnville
— 3 nights
Drive
4
Lincoln City
— 2 nights
Drive
5
Florence
— 1 night
Drive
6
Bandon
— 2 nights
Drive
7
Gold Beach
— 2 nights
Drive
8
Brookings
— 4 nights
Drive
9
Grants Pass
— 2 nights
Drive
10
Prospect
— 2 nights
Drive
11
Bend
— 5 nights
Fly
12
Hood River
— 4 nights
Fly

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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.
Discover out-of-the-way places like Rice NW Museum of Rocks and Minerals and Peninsula Park and Rose Gardens. Visiting Waterfront Renaissance Trail and Powell Butte Nature Park will get you outdoors. You'll find plenty of places to visit near Portland: The Chehalis Centralia Railroad & Museum (in Chehalis), Steigerwald Lake National Wildlife Refuge (in Washougal) and Ardiri Winery and Vineyards (in Cornelius). There's much more to do: visit Northwest (Nob Hill), sample the fine beverages at Westward Whiskey, snap pictures at Tilikum Crossing, and take a stroll through Multnomah Village.

To find maps, reviews, photos, and more tourist information, go to the Portland trip planning tool.

Orlando to Portland is an approximately 8-hour flight. You can also drive; or do a combination of bus and train. Traveling from Orlando to Portland, you'll gain 3 hours due to the time zone difference. In May, Portland is a bit cooler than Orlando - with highs of 70°F and lows of 51°F. Wrap up your sightseeing on the 19th (Tue) to allow time to drive to Astoria.
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Parks · Wildlife · Trails · Outdoors
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Find places to stay May 15 — 19:

Astoria — 2 nights

Spirit of the Columbia

Astoria, named for famed fur trader John Jacob Astor, resides near the mouth of the Columbia River.
Kick off your visit on the 20th (Wed): immerse yourself in nature at Oswald West State Park, see the interesting displays at Heritage Museum, and then learn about winemaking at Shallon Winery. Here are some ideas for day two: examine the collection at Flavel House Museum.

To see more things to do, reviews, and tourist information, you can read our Astoria trip planning tool.

You can drive from Portland to Astoria in 2 hours. Another option is to take a bus. Expect slightly colder weather when traveling from Portland in May: highs in Astoria hover around 62°F, while lows dip to 48°F. Wrap up your sightseeing on the 21st (Thu) to allow time to drive to McMinnville.
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Museums · Nature · Parks · Wineries
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Find places to stay May 19 — 21:

McMinnville — 3 nights

McMinnville is the county seat and largest city of Yamhill County, Oregon, United States. Get ready for a full day of sightseeing on the 22nd (Fri): do a tasting 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 learn about winemaking at Willamette Valley Vineyards Wine Center.

Before you visit McMinnville, use our trip planner to discover what you can do and see there.

You can drive from Astoria to McMinnville in 2.5 hours. Alternatively, you can do a combination of bus and tram; or take a bus. Expect somewhat warmer weather when traveling from Astoria in May: highs in McMinnville hover around 70°F, while lows dip to 47°F. Finish up your sightseeing early on the 24th (Sun) so you can go by car to Lincoln City.
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Wineries · Museums
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Find places to stay May 21 — 24:

Lincoln City — 2 nights

Lincoln City is a city in Lincoln County, Oregon, United States. Start off your visit on the 24th (Sun): take in the views from Drift Creek Covered Bridge, get maximum retail therapy with Pacific Artists Alliance Co-op Gallery, get engrossed in the history at Prehistoric, take in the exciting artwork at Rock Your World: Pacific Northwest Gem & Jewelry Gallery, then shop like a local with Freed Gallery, and finally view the masterpieces at Mossy Creek Pottery. Keep things going the next day: stroll around Siletz Bay Park, 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 ratings, where to stay, more things to do, and other tourist information, go to the Lincoln City day trip app.

Getting from McMinnville to Lincoln City by car takes about 1.5 hours. Other options: 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) so you can drive to Florence.
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Parks · Museums · Shopping · Beaches
Side Trip
Find places to stay May 24 — 26:

Florence — 1 night

Florence is a coastal city in Lane County, in the U.S. state of Oregon. Start off your visit on the 26th (Tue): tour the pleasant surroundings at Heceta Beach, tee off at Ocean Dunes Golf Links, and then stroll through Hobbit Trail.

For photos, where to stay, ratings, and tourist information, refer to the Florence trip planner.

Traveling by car from Lincoln City to Florence takes 2 hours. Alternatively, you can take a bus. In May, daily temperatures in Florence can reach 62°F, while at night they dip to 49°F. Wrap up your sightseeing on the 27th (Wed) to allow time to drive to Bandon.
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Outdoors · Parks · Golf · Trails
Find places to stay May 26 — 27:

Bandon — 2 nights

Bandon is a city in Coos County, Oregon, United States, on the south side of the mouth of the Coquille River. Start off your visit on the 27th (Wed): immerse yourself in nature at Port Orford Heads State Park, examine the collection at Port Orford Lifeboat Station Museum, then look for gifts at Misty Meadows Jams, and finally stroll through Bandon State Park. Get ready for a full day of sightseeing on the next day: hike along South Slough National Estuarine Research Reserve, then play a few rounds at Pacific Dunes, and then stroll through Coquille Point.

To see reviews, ratings, where to stay, and more tourist information, read our Bandon trip itinerary 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. Cap off your sightseeing on the 29th (Fri) early enough to go by car to Gold Beach.
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Outdoors · Parks · Nature · Golf
Side Trips
Find places to stay May 27 — 29:

Gold Beach — 2 nights

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, then stop by Gold Beach Books, then kick back and relax at Ophir Beach, and finally kick back and relax at Myers Creek Beach. Keep things going the next day: contemplate the waterfront views at Illinois River and then play a few rounds at Cedar Bend Golf Club.

For other places to visit, ratings, maps, and tourist information, you can read our Gold Beach trip tool.

You can drive from Bandon to Gold Beach in 1.5 hours. Alternatively, you can take a bus. Expect a daytime high around 63°F in May, and nighttime lows around 48°F. Wrap up your sightseeing on the 31st (Sun) to allow time to drive to Brookings.
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Outdoors · Parks · Beaches · Golf
Side Trips
Find places to stay May 29 — 31:

Brookings — 4 nights

Brookings is a city in Curry County, Oregon, United States. Do some cultural sightseeing at End of the Trail Museum and Del Norte County History Museum. Discover out-of-the-way places like Samuel H. Boardman State Scenic Corridor and Crissey Field State Park. Change things up with these side-trips from Brookings: Crescent City (Point St George Park & Northcoast Marine Mammal Center) and Enderts Beach (in Redwood National Park). Next up on the itinerary: enjoy the sand and surf at Lone Ranch Beach, admire the majestic nature at McVay Rock State Recreation Site, get great views at Natural Bridges Viewpoint, and admire all the interesting features of Welcome to California.

Start your trip to Brookings by creating a personalized itinerary on Inspirock.

Getting from Gold Beach to Brookings by car takes about an hour. Expect a daytime high around 63°F in May, and nighttime lows around 48°F. Wrap up your sightseeing on the 4th (Thu) to allow time to drive to Grants Pass.
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Find places to stay May 31 — Jun 4:

Grants Pass — 2 nights

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 stroll the grounds of Jacksonville Cemetery, then do a tasting at Troon Vineyard, and finally stroll around Schroeder County Park. Here are some ideas for day two: experience rural life at Rogue Creamery Dairy Farm, admire the masterpieces at Grants Pass Museum of Art, see the interesting displays at Schmidt House Museum, 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.

To see traveler tips, where to stay, reviews, and other tourist information, you can read our Grants Pass trip planner.

Traveling by car from Brookings to Grants Pass takes 2 hours. June in Grants Pass sees daily highs of 70°F and lows of 49°F at night. Wrap up your sightseeing on the 6th (Sat) to allow time to drive to Prospect.
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Museums · Wineries · Parks · Historic Sites
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Find places to stay Jun 4 — 6:

Prospect — 2 nights

Prospect is an unincorporated community in Jackson County, in the U.S. state of Oregon. Kick off your visit on the 6th (Sat): admire the sheer force of Plaikni Falls, then take in the awesome beauty at Watchman Peak, then tour the pleasant surroundings at Pinnacles Trail, and finally tour the pleasant surroundings at Castle Crest Wildflower Trail. Here are some ideas for day two: get great views at Natural Bridge Viewpoint, trek along Annie Creek Canyon, and then contemplate the geological forces at Mount Scott.

For maps, where to stay, ratings, and tourist information, refer to the Prospect trip itinerary builder website.

You can drive from Grants Pass to Prospect in 1.5 hours. Plan for a bit warmer temperatures traveling from Grants Pass in June, with highs in Prospect at 86°F and lows at 55°F. Finish your sightseeing early on the 8th (Mon) to allow enough time to drive to Bend.
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Parks · Trails · Outdoors · Nature
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Find places to stay Jun 6 — 8:

Bend — 5 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.
Satisfy your inner culture vulture at City of Sisters and The Museum at Warm Springs. Eschew the tourist crowds and head to Deschutes Brewery and Oregon Badlands Wilderness Trails. You'll find plenty of places to visit near Bend: Erickson Aircraft Collection (in Madras), Peterson Ridge Trail (in Sisters) and Tumalo Mountain (in Redmond). There's lots more to do: look and learn at Dee Wright Observatory, take in the awesome beauty at South Sister, stop by Artists Gallery Sunriver, and indulge your thirst for a good beer at Atlas Cider Co.

For photos, other places to visit, more things to do, and other tourist information, read our Bend road trip planning tool.

Traveling by car from Prospect to Bend takes 2.5 hours. Expect little chillier temperatures when traveling from Prospect in June; daily highs in Bend reach 75°F and lows reach 45°F. Finish up your sightseeing early on the 13th (Sat) so you can catch the flight to Hood River.
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Find places to stay Jun 8 — 13:

Hood River — 4 nights

The city of Hood River is the seat of Hood River County, Oregon, United States. Let the collections at Presby Museum and Art on Oak capture your imagination. Eschew the tourist crowds and head to Cathedral Ridge Winery and Panorama Point County Park. Get out of town with these interesting Hood River side-trips: Stonehenge Memorial (in Goldendale) and Columbia Hills State Park (in Dallesport). There's lots more to do: do a tasting at Mt. Hood Winery, stroll through Rowena Crest Viewpoint, and see the interesting displays at Fire Museum in City Hall.

For traveler tips, more things to do, maps, and other tourist information, refer to the Hood River online trip itinerary planner.

You can fly from Bend to Hood River in 2.5 hours. Alternatively, you can drive; or take a bus. Plan for a bit warmer nights when traveling from Bend in June since evenings lows in Hood River dip to 55°F. Wrap up your sightseeing by early afternoon on the 17th (Wed) to allow time for the flight back home.
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Wineries · Parks · Nature · Historic Sites
Side Trips
Find places to stay Jun 13 — 17:

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.
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