12 days in Oregon Itinerary

12 days in Oregon Itinerary

Created using Inspirock Oregon trip itinerary planner

Make it your trip
Fly
1
Portland
— 1 night
Drive
2
Bridal Veil
— 1 night
Drive
3
Hood River
— 1 night
Drive
4
Drake Crossing
— 2 nights
Drive
5
Cannon Beach
— 1 night
Drive
6
Umpqua
— 1 night
Drive
7
Allegany
— 1 night
Drive
8
Brookings
— 1 night
Drive
9
Sisters
— 1 night
Drive to Roberts Field, Fly to Louis Armstrong New Orleans International Airport

S M T W T F S
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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.
Start off your visit on the 18th (Tue): take in the dramatic scenery at Multnomah Falls and then take in the dramatic natural features at Oneonta Gorge.

For other places to visit, maps, traveler tips, and more tourist information, go to the Portland vacation planner.

New Orleans to Portland is an approximately 9.5-hour flight. You can also drive; or take a bus. Due to the time zone difference, you'll gain 2 hours traveling from New Orleans to Portland. Traveling from New Orleans in May, expect a bit cooler with lows of 51°F in Portland. On the 19th (Wed), you'll travel to Bridal Veil.

Things to do in Portland

Nature · Parks · Trails · Outdoors

Side Trips

Bridal Veil

— 1 night
Bridal Veil is a virtual ghost town located in Multnomah County, Oregon, United States. On the 20th (Thu), trek along Angels Rest Trail and then immerse yourself in nature at Beacon Rock State Park.

To see traveler tips, maps, other places to visit, and tourist information, go to the Bridal Veil trip planner.

Getting from Portland to Bridal Veil by car takes about an hour. Other options: drive; or take a bus. In May in Bridal Veil, expect temperatures between 67°F during the day and 49°F at night. Wrap up your sightseeing on the 20th (Thu) early enough to drive to Hood River.

Things to do in Bridal Veil

Parks · Nature · Trails · Outdoors

Side Trip

Highlights from your trip

Hood River

— 1 night
The city of Hood River is the seat of Hood River County, Oregon, United States. On the 21st (Fri), tour the pleasant surroundings at Mount Hood, admire the majestic nature at Starvation Creek State Park, and then trek along Horsetail Falls- Columbia River Gorge.

To see where to stay, maps, ratings, and tourist information, go to the Hood River trip planner.

Getting from Bridal Veil to Hood River by car takes about an hour. Other options: take a bus. In May, plan for daily highs up to 67°F, and evening lows to 49°F. Finish your sightseeing early on the 21st (Fri) to allow enough time to travel to Drake Crossing.

Things to do in Hood River

Parks · Outdoors · Nature · Trails

Side Trip

Drake Crossing

— 2 nights
Kick off your visit on the 22nd (Sat): take in the dramatic scenery at Butte Creek Falls and then immerse yourself in nature at Silver Falls State Park.

To see other places to visit, ratings, maps, and other tourist information, read our Drake Crossing tour planner.

Getting from Hood River to Drake Crossing by car takes about 2 hours. Wrap up your sightseeing on the 23rd (Sun) early enough to travel to Cannon Beach.

Things to do in Drake Crossing

Nature · Parks

Side Trip

Highlights from your trip

Cannon Beach

— 1 night
Cannon Beach is a city in Clatsop County, Oregon, United States. Kick off your visit on the 23rd (Sun): stroll through Haystack Rock, then admire the majestic nature at Ecola State Park, and then admire the majestic nature at Oswald West State Park.

To find more things to do, ratings, reviews, and other tourist information, refer to the Cannon Beach day trip planning site.

Traveling by car from Drake Crossing to Cannon Beach takes 2.5 hours. In May, daily temperatures in Cannon Beach can reach 62°F, while at night they dip to 48°F. Wrap up your sightseeing on the 24th (Mon) early enough to travel to Umpqua.

Things to do in Cannon Beach

Nature · Parks · Beaches · Outdoors

Umpqua

— 1 night
Umpqua is an unincorporated community in Douglas County, in the U.S. state of Oregon. You've now added Umpqua National Forest to your itinerary. Here are some ideas for day two: delve into the lush surroundings at Umpqua National Forest, then do a tasting at Henry Estate Winery, and then take in the views from Rochester Covered Bridge.

To find other places to visit, traveler tips, and more tourist information, refer to the Umpqua trip planner.

Drive from Cannon Beach to Umpqua in 4 hours. Traveling from Cannon Beach in May, expect nights in Umpqua to be about the same, around 50°F, while days are a bit warmer, around 73°F. Wrap up your sightseeing on the 25th (Tue) early enough to travel to Allegany.

Things to do in Umpqua

Wineries · Nature · Parks

Side Trip

Allegany

— 1 night
Allegany is an unincorporated community in Coos County, Oregon, United States. On the 26th (Wed), admire the sheer force of Golden and Silver Falls State Natural Area.

To see photos, other places to visit, ratings, and tourist information, refer to the Allegany trip planner.

You can drive from Umpqua to Allegany in 2.5 hours. Traveling from Umpqua in May, expect nights in Allegany to be about the same, around 49°F, while days are a bit cooler, around 62°F. Wrap up your sightseeing by early afternoon on the 26th (Wed) to allow time for travel to Brookings.

Things to do in Allegany

Nature · Parks

Brookings

— 1 night
Brookings is a city in Curry County, Oregon, United States. For photos, reviews, and other tourist information, read our Brookings trip tool.

Drive from Allegany to Brookings in 2.5 hours. In May, daily temperatures in Brookings can reach 63°F, while at night they dip to 48°F. On the 27th (Thu), wrap the sightseeing up by early afternoon so you can travel to Sisters.

Things to do in Brookings

Parks · Outdoors · Beaches · Trails

Sisters

— 1 night
Sisters is a city in Deschutes County, Oregon, United States. Kick off your visit on the 28th (Fri): admire all the interesting features of McKenzie Pass-Santiam Pass loop, admire the sheer force of Sahalie and Koosah Falls, and then stop by City of Sisters.

To find ratings, where to stay, more things to do, and more tourist information, read Sisters trip maker tool.

You can drive from Brookings to Sisters in 6 hours. Another option is to do a combination of car and flight. When traveling from Brookings in May, plan for a bit warmer days in Sisters, with highs around 70°F, while nights are slightly colder with lows around 37°F. Cap off your sightseeing on the 28th (Fri) early enough to travel back home.

Things to do in Sisters

Nature · Parks · Scenic Drive · Outdoors

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.