15 days in Oregon Itinerary

Created using Inspirock Oregon trip itinerary planner
Make it your trip
Fly
1
Portland
— 2 nights
Drive
2
Coos Bay
— 2 nights
Drive
3
Medford
— 4 nights
Drive
4
Crater Lake National Park
— 2 nights
Drive
5
Bend
— 2 nights
Fly
6
Portland
— 1 night
Fly

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Portland — 2 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 discover tucked-away gems like Oregon City Municipal Elevator and Museum of the Oregon Territory. Get a sense of the local culture at Northwest (Nob Hill) and Oregon Jewish Museum and Center For Holocaust Education. Step out of Portland to go to Hillsboro and see Jackson Bottom Wetlands Preserve, which is approximately 32 minutes away. The adventure continues: identify plant and animal life at Cooper Mountain Nature Park, take in the exciting artwork at Freakybuttrue Peculiarium, take in the views from Tilikum Crossing, and take a peaceful walk through Camassia Natural Area.

To find where to stay, traveler tips, photos, and other tourist information, go to the Portland trip builder app.

New York City to Portland is an approximately 8-hour flight. You can also drive; or take a train. Due to the time zone difference, you'll gain 3 hours traveling from New York City to Portland. Expect a bit cooler evenings in Portland when traveling from New York City in August, with lows around 60°F. Finish your sightseeing early on the 10th (Wed) to allow enough time to drive to Coos Bay.
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Wildlife · Parks · Museums · Shopping
Side Trips
Find places to stay Aug 8 — 10:

Coos Bay — 2 nights

Coos Bay is a city located in Coos County, Oregon, United States, where the Coos River enters Coos Bay on the Pacific Ocean. On the 11th (Thu), play a few rounds at Coos Golf Club, then enjoy the sand and surf at Bandon State Park, then enjoy the sand and surf at Coquille Point, and finally take in the exciting artwork at Second Street Gallery. On the 12th (Fri), you'll have a packed day of sightseeing: stroll the grounds of Marshfield Pioneer Cemetery, examine the collection at Coos Art Museum, then make a trip to Steve Prefontaine Murals, then take an in-depth tour of Coos History Museum, and finally take in the views from McCullough Memorial Bridge.

To find out how to plan a trip to Coos Bay, use our trip itinerary maker.

You can drive from Portland to Coos Bay in 4 hours. Expect a bit cooler temperatures when traveling from Portland in August; daily highs in Coos Bay reach 68°F and lows reach 54°F. Finish your sightseeing early on the 12th (Fri) so you can drive to Medford.
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Outdoors · Museums · Parks · Beaches
Side Trip
Find places to stay Aug 10 — 12:

Medford — 4 nights

Medford is a city in, and county seat of, Jackson County, Oregon, United States. Your cultural itinerary includes sights like Jacksonville Cemetery and 2Hawk Vineyard & Winery. You'll explore and learn at Grants Pass Museum of Art and Gathering Glass Studio. Get out of town with these interesting Medford side-trips: ROW Adventures - Rogue River Rafting (in Merlin) and Pacific Crest National Scenic Trail (in Dufur). The adventure continues: explore the activities along Applegate Lake, do a tasting at RoxyAnn Winery, walk around Bear Creek Park, and examine the collection at Darkwing Manor & Morguetorium Museum.

Find out how to plan Medford trip without stress by asking Inspirock to help create an itinerary.

You can drive from Coos Bay to Medford in 3 hours. Traveling from Coos Bay in August, you will find days in Medford are much warmer (93°F), and nights are a bit warmer (60°F). Cap off your sightseeing on the 16th (Tue) early enough to go by car to Crater Lake National Park.
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Parks · Outdoors · Wineries · Museums
Side Trips
Find places to stay Aug 12 — 16:

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.
To find traveler tips, photos, ratings, and more tourist information, use the Crater Lake National Park road trip site.

Traveling by car from Medford to Crater Lake National Park takes 2 hours. In August, daytime highs in Crater Lake National Park are 93°F, while nighttime lows are 60°F. Wrap up your sightseeing on the 18th (Thu) early enough to drive to Bend.
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Parks · Trails · Outdoors · Nature
Find places to stay Aug 16 — 18:

Bend — 2 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.
Museum-lovers will get to explore Oregon Observatory and Des Chutes Historical Museum. Step off the beaten path and head to Todd Lake and Sunriver Nature Center. Change things up with a short trip to Tumalo Mountain in Redmond (about 34 minutes away). There's much more to do: delve into the lush surroundings at Shevlin Park, trek along Oregon Badlands Wilderness Trails, take in the awesome beauty at South Sister, and walk around Drake Park.

For where to stay, reviews, and other tourist information, go to the Bend road trip tool.

Getting from Crater Lake National Park to Bend by car takes about 2.5 hours. Other options: do a combination of taxi and bus. Expect slightly colder temperatures when traveling from Crater Lake National Park in August; daily highs in Bend reach 84°F and lows reach 52°F. Wrap up your sightseeing on the 20th (Sat) early enough to fly to Portland.
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Parks · Nature · Trails · Outdoors
Side Trips
Find places to stay Aug 18 — 20:

Portland — 1 night

City of Roses

Kick off your visit on the 21st (Sun): snap pictures at Tilikum Crossing and then take a stroll through Northwest (Nob Hill).

To find maps, other places to visit, where to stay, and tourist information, refer to the Portland trip tool.

Traveling by flight from Bend to Portland takes 2.5 hours. Alternatively, you can drive; or take a bus. Traveling from Bend in August, plan for somewhat warmer nights in Portland, with lows around 60°F. Cap off your sightseeing on the 21st (Sun) early enough to catch the flight back home.
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Historic Sites · Shopping · Neighborhoods
Find places to stay Aug 20 — 21:

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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