29 days in Oregon Itinerary

29 days in Oregon Itinerary

Created using Inspirock United States visit planner

Make it your trip
Drive
1
Cannon Beach
— 4 nights
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2
Newport
— 3 nights
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3
Florence
— 3 nights
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4
Bandon
— 4 nights
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5
Brookings
— 2 nights
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6
Portland
— 1 night
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7
Hood River
— 2 nights
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8
Crater Lake National Park
— 2 nights
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9
Bend
— 3 nights
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Cannon Beach

— 4 nights
Cannon Beach is a city in Clatsop County, Oregon, United States. Head to Wheeler Station Antiques and DragonFire Galleryfor plenty of shopping. Museum-lovers will get to explore International Police Museum and Cannon Beach History Center and Museum. Step out of Cannon Beach to go to Rockaway Beach and see Cedar Wetlands Preserve, which is approximately 38 minutes away. Next up on the itinerary: indulge in some personalized pampering at some of the best spas, enjoy the sand and surf at Hug Point State Recreation Site, tour the pleasant surroundings at Short Sands Beach, and brush up on your knowledge of spirits at Cannon Beach Distillery.

To see photos, where to stay, other places to visit, and tourist information, read our Cannon Beach trip itinerary maker website.

Cincinnati to Cannon Beach is an approximately 39-hour car ride. You can also fly; or drive; or do a combination of bus and train. The time zone changes from Eastern Standard Time (EST) to Pacific Standard Time (PST), which is usually a -3 hour difference. Expect a bit cooler temperatures when traveling from Cincinnati in August; daily highs in Cannon Beach reach 71°F and lows reach 55°F. Wrap up your sightseeing on the 6th (Thu) to allow time to drive to Newport.

Things to do in Cannon Beach

Outdoors · Parks · Beaches · Shopping

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.
Get a sense of the local culture at Ripley's Believe It or Not! and The Wax Works. Give yourself a bit of retail therapy at Inscapes Gallery and Newport Farmer's Market. There's lots more to do: snap pictures at Yaquina Bay Bridge, brush up on your military savvy at Pacific Maritime and Heritage Center, see the interesting displays at Burrows House Museum, and hike along Ocean to Bay Trail.

To see reviews, photos, where to stay, and tourist information, read Newport day trip planning website.

Drive from Cannon Beach to Newport in 3 hours. Alternatively, you can drive; or take a bus. While traveling from Cannon Beach, expect little chillier days and about the same nights in Newport, ranging from highs of 64°F to lows of 51°F. Finish up your sightseeing early on the 9th (Sun) so you can go by car to Florence.

Things to do in Newport

Museums · Breweries & Distilleries · Shopping · Trails

Florence

— 3 nights
Florence is a coastal city in Lane County, in the U.S. state of Oregon. Visiting Thor's Well and Heceta Beach will get you outdoors. Get some cultural insight at Umpqua River Lighthouse, Museum,and Gift shop and Umpqua Discovery Center. When in Florence, make a side trip to see Dean Creek Elk Viewing Area in Reedsport, approximately Reedsport away. Next up on the itinerary: take a memorable drive along Oregon Coast, trek along Hobbit Trail, examine the collection at Siuslaw Pioneer Museum, and view the masterpieces at Backstreet Gallery.

To see maps, more things to do, photos, and tourist information, you can read our Florence road trip website.

You can drive from Newport to Florence in 1.5 hours. Alternatively, you can drive; or take a bus. In August in Florence, expect temperatures between 68°F during the day and 54°F at night. Finish your sightseeing early on the 12th (Wed) so you can drive to Bandon.

Things to do in Florence

Museums · Parks · Outdoors · Shopping

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. Head to Cranberry Sweets and Second Street Galleryfor some retail therapy. Do some cultural sightseeing at Coos Art Museum and Washed Ashore - Gallery & Workshop. Venture out of the city with trips to Coos History Museum (in Coos Bay), Bastendorff Beach (in Charleston) and Off-Road Tours (in North Bend). There's much more to do: enjoy the sand and surf at Bandon State Park, stroll through Whiskey Run Beach, tee off at Pacific Dunes, and trek along South Slough National Estuarine Research Reserve.

To find other places to visit, where to stay, maps, and tourist information, use the Bandon trip planner.

You can drive from Florence to Bandon in 1.5 hours. Other options are to drive; or take a bus. In August in Bandon, expect temperatures between 68°F during the day and 54°F at night. Finish up your sightseeing early on the 16th (Sun) so you can travel to Brookings.

Things to do in Bandon

Outdoors · Parks · Museums · Beaches

Side Trips

Brookings

— 2 nights
Brookings is a city in Curry County, Oregon, United States. Get outdoors at Lone Ranch Beach and McVay Rock State Recreation Site. Step off the beaten path and head to Cape Sebastian State Scenic Corridor and Curry Historical Museum. You'll find plenty of places to visit near Brookings: Gold Beach (The Mary D Hume & Gold Beach Books). Next up on the itinerary: tour the pleasant surroundings at Oregon Redwood Trail, take a memorable drive along Welcome to California, admire the majestic nature at Crissey Field State Park, and sample the tasty concoctions at Chetco Brewing Company.

For maps, photos, reviews, and tourist information, read our Brookings day trip planning website.

You can drive from Bandon to Brookings in 2 hours. Another option is to drive. In August, daily temperatures in Brookings can reach 68°F, while at night they dip to 53°F. Wrap up your sightseeing on the 18th (Tue) early enough to drive to Portland.

Things to do in Brookings

Parks · Nature · Outdoors · Breweries & Distilleries

Side Trips

Portland

— 1 night

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.
Kick off your visit on the 19th (Wed): stroll around Director Park, then get a sense of history and politics at Pioneer Courthouse, and then sample the tasty concoctions at Commons Brewery. Get ready for a full day of sightseeing on the 20th (Thu): admire the sheer force of Jamison Square, look for gifts at The Meadow, then see the interesting displays at Freakybuttrue Peculiarium, then see the interesting displays at Oregon Nikkei Legacy Center, and finally contemplate the long history of Japanese American Historical Plaza.

To see where to stay, reviews, and more tourist information, read Portland trip itinerary builder website.

Traveling by car from Brookings to Portland takes 6 hours. Alternatively, you can drive. In August, Portland is somewhat warmer than Brookings - with highs of 85°F and lows of 60°F. Wrap up your sightseeing on the 20th (Thu) to allow time to drive to Hood River.

Things to do in Portland

Parks · Historic Sites · Breweries & Distilleries · Fun & Games

Hood River

— 2 nights
The city of Hood River is the seat of Hood River County, Oregon, United States. On the 21st (Fri), walk around Port Marina Park, get outside with Big Winds, explore the activities along White Salmon River, then learn about winemaking at Idiot's Grace, and finally do a tasting at Cor Cellars. On your second day here, trek along Mitchell Point Trail, learn about winemaking at Stave & Stone Winery (Downtown Tasting Room), then take in the exciting artwork at Art on Oak, and finally sample the fine beverages at Hood River Distillers Tasting Room.

You can plan Hood River trip in no time by asking Inspirock to help create your itinerary.

Drive from Portland to Hood River in 1.5 hours. Alternatively, you can drive; or take a bus; or take a train. Expect a daytime high around 81°F in August, and nighttime lows around 60°F. Wrap up your sightseeing on the 22nd (Sat) early enough to drive to Crater Lake National Park.

Things to do in Hood River

Wineries · Parks · Outdoors · Trails

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.
Start off your visit on the 23rd (Sun): trek along Pinnacles Trail, stroll through Annie Creek Canyon, then take in the dramatic scenery at Vidae Falls, and finally hike along Sun Notch Trail. On your second day here, take in the dramatic scenery at Plaikni Falls, then stroll through Mount Scott, and then tour the pleasant surroundings at Castle Crest Wildflower Trail.

To see photos, other places to visit, and more tourist information, read Crater Lake National Park tour itinerary planner.

You can drive from Hood River to Crater Lake National Park in 6 hours. Alternatively, you can drive; or fly; or do a combination of bus and taxi. While traveling from Hood River, expect a bit warmer days and about the same nights in Crater Lake National Park, ranging from highs of 93°F to lows of 60°F. Wrap up your sightseeing on the 24th (Mon) early enough to drive to Bend.

Things to do in Crater Lake National Park

Parks · Trails · Outdoors · Nature

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.
Kick off your visit on the 25th (Tue): indulge in some personalized pampering at some of the best spas, then go for a walk through Deschutes River Trail, and then look for gifts at Dudley's Bookshop Cafe. Get ready for a full day of sightseeing on the 26th (Wed): walk around Drake Park, then contemplate the waterfront views at Little Cultus Lake, then sample the tasty concoctions at Atlas Cider Co, and finally indulge your thirst for a good beer at Boneyard Beer.

For photos, other places to visit, maps, and more tourist information, read Bend trip planner.

You can drive from Crater Lake National Park to Bend in 3 hours. Other options are to drive; or do a combination of taxi and bus. Traveling from Crater Lake National Park in August, expect Bend to be a bit cooler, temps between 84°F and 52°F. Wrap up your sightseeing by early afternoon on the 27th (Thu) to allow time for travel back home.

Things to do in Bend

Parks · Trails · Outdoors · Nature

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.