15 days in Oregon Itinerary

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

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 Jackson Bottom Wetlands Preserve. Get a sense of the local culture at Museum of the Oregon Territory and Freakybuttrue Peculiarium. The adventure continues: tour the pleasant surroundings at Cooper Mountain Nature Park, explore the world behind art at Oregon Jewish Museum and Center For Holocaust Education, take a stroll through Northwest (Nob Hill), and pick up some local products at Portland Farmers Market - Office Location.

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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Parks · Wildlife · Museums · Shopping
Side Trips

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 travel to Medford.
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Outdoors · Museums · Parks · Beaches
Side Trip

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 Southern Oregon Historical Society. You'll explore and learn at Grants Pass Museum of Art and Darkwing Manor & Morguetorium Museum. 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, walk around Bear Creek Park, do a tasting at RoxyAnn Winery, and tour the pleasant surroundings at North Mountain Park.

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

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

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 Sunriver Nature Center. Step off the beaten path and head to Todd Lake and Shevlin Park. Change things up with a short trip to Tumalo Mountain in Redmond (about 34 minutes away). Next up on the itinerary: take your sightseeing to a higher altitude at South Sister, stroll around Drake Park, grab your bike and head to Deschutes River Trail, and get engrossed in the history at Des Chutes Historical Museum.

For traveler tips, ratings, reviews, and other tourist information, use the Bend trip itinerary planner.

You can drive from Crater Lake National Park to Bend in 2.5 hours. Alternatively, you can do a combination of taxi and bus. Traveling from Crater Lake National Park in August, things will get slightly colder in Bend: highs are around 84°F and lows about 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

Portland — 1 night

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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Shopping · Historic Sites · Neighborhoods

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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