23 days in Oregon Itinerary

23 days in Oregon Itinerary

Created using Inspirock Oregon holiday planner
Make it your trip
Fly
1
Portland
— 4 nights
Drive
2
Hood River
— 3 nights
Fly
3
Bend
— 3 nights
Drive
4
Crater Lake National Park
— 2 nights
Drive
5
Ashland
— 2 nights
Drive
6
Florence
— 2 nights
Drive
7
Newport
— 2 nights
Drive
8
Astoria
— 4 nights
Drive to Seattle Tacoma International Airport, Fly to Halifax

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Portland — 4 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.
Explore Portland's surroundings by going to Evergreen Aviation & Space Museum (in McMinnville) and Multnomah Falls (in Bridal Veil). Dedicate the 9th (Sat) to wine at some of the top wineries in the area. There's still lots to do: admire the natural beauty at International Rose Test Garden, stop by Powell's City of Books, make a trip to Pittock Mansion, and trek along Forest Park.

To see maps, ratings, traveler tips, and more tourist information, you can read our Portland trip itinerary maker.

Halifax, Canada to Portland is an approximately 12.5-hour flight. You can also drive; or take a train. The time zone difference moving from Atlantic Standard Time to Pacific Standard Time is minus 4 hours. Traveling from Halifax in July, expect nights in Portland to be about the same, around 17°C, while days are a bit warmer, around 33°C. Wrap up your sightseeing on the 10th (Sun) early enough to drive to Hood River.
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Tours · Parks · Wineries · Museums
Side Trips

Hood River — 3 nights

The city of Hood River is the seat of Hood River County, Oregon, United States. Hood River is known for wineries, nature, and trails. Your trip includes some of its best attractions: tour the pleasant surroundings at Columbia River Gorge National Scenic Area, take in the awesome beauty at Mount Hood, cruise along Hood River County Fruit Loop, and take a peaceful walk through Mt. Hood National Forest.

For traveler tips, reviews, ratings, and other tourist information, read our Hood River planner.

Traveling by car from Portland to Hood River takes 1.5 hours. Alternatively, you can take a bus; or take a train. Expect a daytime high around 30°C in July, and nighttime lows around 17°C. Finish your sightseeing early on the 13th (Wed) to allow enough time to fly to Bend.
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Parks · Nature · Outdoors · Trails
Side Trips

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.
Step out of Bend with an excursion to Smith Rock State Park in Redmond--about 38 minutes away. And it doesn't end there: let the river carry you with a rafting and tubing tour, explore the activities along Deschutes River, see the interesting displays at High Desert Museum, and learn something new at The Art of Alfred A. Dolezal Gallery.

For reviews, where to stay, photos, and more tourist information, read our Bend online route planner.

Getting from Hood River to Bend by flight takes about 2.5 hours. Other options: drive; or take a bus. Traveling from Hood River in July, you will find days in Bend are a bit warmer (34°C), and nights are slightly colder (13°C). Cap off your sightseeing on the 16th (Sat) early enough to go by car to Crater Lake National Park.
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Parks · Nature · Museums · Outdoors
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.
Kick off your visit on the 17th (Sun): explore the wealth of natural beauty at Crater Lake National Park. Get ready for a full day of sightseeing on the 18th (Mon): stroll through Cleetwood Cove Trail and then take a memorable drive along Rim Dr.

For ratings, traveler tips, where to stay, and more tourist information, go to the Crater Lake National Park trip itinerary maker site.

Traveling by car from Bend to Crater Lake National Park takes 2.5 hours. Alternatively, you can do a combination of bus and taxi. In July, Crater Lake National Park is somewhat warmer than Bend - with highs of 40°C and lows of 19°C. Wrap up your sightseeing on the 18th (Mon) early enough to drive to Ashland.
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Parks · Nature · Outdoors · Trails

Ashland — 2 nights

Ashland is a city in Jackson County, in the State of Oregon. Start off your visit on the 19th (Tue): take a tour by water with Boat Tours & Water Sports and then walk around Lithia Park. Here are some ideas for day two: see a show at Oregon Shakespeare Festival, then look for gifts at Tudor Guild Shop, and then explore the activities along Rogue River.

To see ratings, where to stay, maps, and other tourist information, use the Ashland online tour planner.

Traveling by car from Crater Lake National Park to Ashland takes 2 hours. Alternatively, you can do a combination of taxi and bus. Expect a daytime high around 40°C in July, and nighttime lows around 19°C. Cap off your sightseeing on the 20th (Wed) early enough to go by car to Florence.
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Parks · Shopping · Tours · Nightlife
Side Trip

Florence — 2 nights

Florence is a coastal city in Lane County, in the U.S. state of Oregon. On the 21st (Thu), Head underground at Sea Lion Caves and then experience the excitement of Sandland Adventures. On the 22nd (Fri), you'll have a packed day of sightseeing: enjoy the sea views from Heceta Head Lighthouse and then take a memorable drive along Cape Perpetua Visitor Center - Siuslaw National Forest.

To see reviews, where to stay, and tourist information, read our Florence online travel planner.

You can drive from Ashland to Florence in 4.5 hours. Other options are to take a bus; or take a bus. When traveling from Ashland in July, plan for cooler days in Florence, with highs around 22°C, while nights are slightly colder with lows around 14°C. Finish your sightseeing early on the 22nd (Fri) so you can drive to Newport.
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Parks · Nature · Outdoors · Tours
Side Trip

Newport — 2 nights

A town that survives on the sea, Newport's population of just over 10,000 supports a healthy commercial fishing industry.
Start off your visit on the 23rd (Sat): see majestic marine mammals with Marine Discovery Tours, observe the fascinating underwater world at Oregon Coast Aquarium, and then take a leisurely stroll along Yachats coastline. Keep things going the next day: tour the pleasant surroundings at Yaquina Head Outstanding Natural Area, take in the waterfront at Newport's Historic Bayfront, and then look for gifts at Beachtown Charities Thrift and Gift.

To find maps, ratings, reviews, and more tourist information, read our Newport road trip site.

Traveling by car from Florence to Newport takes 1.5 hours. Alternatively, you can take a bus. July in Newport sees daily highs of 20°C and lows of 11°C at night. Cap off your sightseeing on the 24th (Sun) early enough to go by car to Astoria.
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Parks · Wildlife · Zoos & Aquariums · Tours
Side Trips

Astoria — 4 nights

Astoria, named for famed fur trader John Jacob Astor, resides near the mouth of the Columbia River.
Explore the numerous day-trip ideas around Astoria: Cannon Beach (Icefire Glassworks, Haystack Rock, &more). It doesn't end there: pause for some photo ops at Astoria Column and stroll through Fort Clatsop National Memorial.

For more things to do, photos, and tourist information, read our Astoria trip planning tool.

You can drive from Newport to Astoria in 3.5 hours. Alternatively, you can take a bus. Expect somewhat warmer weather when traveling from Newport in July: highs in Astoria hover around 24°C, while lows dip to 15°C. Finish your sightseeing early on the 28th (Thu) to allow enough time to travel back home.
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Parks · Nature · Historic Sites · Beaches
Side Trip

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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