12 days in Oregon Itinerary

12 days in Oregon Itinerary

Created using Inspirock Oregon trip 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.
Kick off your visit on the 18th (Tue): admire the sheer force of Multnomah Falls and then explore the striking landscape at Oneonta Gorge.

To find ratings, traveler tips, reviews, and other tourist information, you can read our Portland tour planner.

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

Things to do in Portland

Parks · Nature · Trails · Outdoors

Side Trips

Bridal Veil

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

To plan Bridal Veil vacation without wasting time, ask Inspirock to design an itinerary.

You can drive from Portland to Bridal Veil in an hour. Alternatively, you can drive; or take a bus. In May in Bridal Veil, expect temperatures between 67°F during the day and 49°F at night. Finish your sightseeing early on the 20th (Thu) so you can drive to Hood River.

Things to do in Bridal Veil

Parks · Trails · Outdoors · Nature

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. Kick off your visit on the 21st (Fri): hit the slopes at Mount Hood, then admire the majestic nature at Starvation Creek State Park, and then hike along Horsetail Falls- Columbia River Gorge.

For maps, reviews, where to stay, and tourist information, read our Hood River trip itinerary builder app.

Traveling by car from Bridal Veil to Hood River takes an hour. Alternatively, you can take a bus. May in Hood River sees daily highs of 67°F and lows of 49°F at night. 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
On the 22nd (Sat), take in the dramatic scenery at Butte Creek Falls and then admire the majestic nature at Silver Falls State Park.

To see maps, traveler tips, other places to visit, and tourist information, refer to the Drake Crossing online attractions planner.

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

Things to do in Drake Crossing

Parks · Nature

Side Trip

Highlights from your trip

Cannon Beach

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

For photos, traveler tips, ratings, and other tourist information, refer to the Cannon Beach online itinerary planner.

You can drive from Drake Crossing to Cannon Beach in 2.5 hours. May in Cannon Beach sees daily highs of 62°F and lows of 48°F at night. Cap off your sightseeing on the 24th (Mon) early enough to travel to Umpqua.

Things to do in Cannon Beach

Parks · Nature · Beaches · Outdoors

Umpqua

— 1 night
Umpqua is an unincorporated community in Douglas County, in the U.S. state of Oregon. Umpqua National Forest has been added to your itinerary. Get ready for a full day of sightseeing on the next day: delve into the lush surroundings at Umpqua National Forest, learn about winemaking at Henry Estate Winery, and then take in the views from Rochester Covered Bridge.

For more things to do, other places to visit, traveler tips, and tourist information, go 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. Finish your sightseeing early on the 25th (Tue) so you can travel to Allegany.

Things to do in Umpqua

Wineries · Parks · Nature

Side Trip

Allegany

— 1 night
Allegany is an unincorporated community in Coos County, Oregon, United States. Start off your visit on the 26th (Wed): take in the dramatic scenery at Golden and Silver Falls State Natural Area.

To find traveler tips, where to stay, maps, and more tourist information, read Allegany day trip planning app.

Traveling by car from Umpqua to Allegany takes 2.5 hours. When traveling from Umpqua in May, plan for slightly colder days in Allegany, with highs around 62°F, while nights are about the same with lows around 49°F. Wrap up your sightseeing by early afternoon on the 26th (Wed) to allow time for travel to Brookings.

Things to do in Allegany

Parks · Nature

Brookings

— 1 night
Brookings is a city in Curry County, Oregon, United States. For reviews, other places to visit, where to stay, and more tourist information, you can read our Brookings attractions planner.

Getting from Allegany to Brookings by car takes about 2.5 hours. May in Brookings sees daily highs of 63°F and lows of 48°F at night. On the 27th (Thu), wrap the sightseeing up by early afternoon so you can travel to Sisters.

Things to do in Brookings

Outdoors · Parks · Beaches · Trails

Sisters

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

To find maps, ratings, and other tourist information, refer to the Sisters driving holiday planner.

You can drive from Brookings to Sisters in 6 hours. Another option is to do a combination of car and flight. Traveling from Brookings in May, expect nights in Sisters to be slightly colder, around 37°F, while days are a bit warmer, around 70°F. Wrap up your sightseeing on the 28th (Fri) early enough to travel back home.

Things to do in Sisters

Outdoors · Scenic Drive · Parks · 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.