21 days in Oregon Itinerary

21 days in Oregon Itinerary

Created using Inspirock Oregon trip itinerary builder

This plan was created by another user.  Make it your plan

Route & dates

21 days in Oregon Itinerary

Start: Lexington
Fly:  8​h 45​min
1
Portland
— 5 nights
Drive:  2​h
2
Astoria
— 5 nights
Drive:  3​h 30​min
3
Newport
— 2 nights
Drive:  1​h 15​min
4
Florence
— 1 night
Drive:  4​h 15​min
5
Ashland
— 4 nights
Drive:  4​h 30​min
6
Bend
— 2 nights
Fly:  11​h
End: Lexington

5
nights
Portland

Portland ©
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.
Your cultural itinerary includes sights like Officers' Row and Columbia Hills State Park. Museum-lovers will get to explore Portland Art Museum and Evergreen Aviation & Space Museum. Change things up with a short trip to Multnomah Falls in Bridal Veil (about 38 minutes away). Dedicate the 12th (Thu) to wine at some of the top wineries in the area. There's much more to do: take a peaceful walk through The Grotto - National Sanctuary of Our Sorrowful Mother, take in nature's colorful creations at Portland Japanese Garden, steep yourself in history at Pittock Mansion, and stop by Powell's City of Books.

To find other places to visit, reviews, traveler tips, and other tourist information, read Portland trip planner .

Lexington to Portland is an approximately 9-hour flight. You can also do a combination of bus and flight; or drive. Traveling from Lexington to Portland, you'll gain 3 hours due to the time zone difference. Traveling from Lexington in September, expect nights in Portland to be about the same, around 55°F, while days are little chillier, around 76°F. Finish your sightseeing early on the 13th (Fri) to allow enough time to drive to Astoria.

Things to do in Portland

Parks Nature Tours

Side Trips

Multnomah Falls, Officers' Row, Evergreen Aviation & Space Museum, Columbia River Gorge National Scenic Area, Columbia Hills State Park
Highlights from your plan
Officers' Row ©
Officers' Row
Columbia Hills State Park ©
Columbia Hills State Park

5
nights
Astoria

Astoria ©
Astoria, named for famed fur trader John Jacob Astor, resides near the mouth of the Columbia River.
Popular historic sites such as Cape Disappointment Lighthouse and North Head Lighthouse are in your itinerary. Eschew the tourist crowds and head to Lewis & Clark Interpretive Center and Cranberry Museum. Get out of town with these interesting Astoria side-trips: Cannon Beach (Cannon Beach, Haystack Rock, & more), Don Nisbett Art Gallery (in Ilwaco) and Long Beach (Marsh's Free Museum & Long Beach). There's still lots to do: snap pictures at Astoria-Megler Bridge, admire the majestic nature at Fort Stevens State Park, contemplate the long history of Middle Village Station Camp, and explore the activities along Columbia River Maritime Museum.

For maps, where to stay, other places to visit, and tourist information, use the Astoria trip planner.

You can drive from Portland to Astoria in 2 hours. Other options are to take a bus; or do a combination of train and bus. While traveling from Portland, expect little chillier days and about the same nights in Astoria, ranging from highs of 69°F to lows of 52°F. Finish your sightseeing early on the 18th (Wed) so you can drive to Newport.

Things to do in Astoria

Parks Nature Museums

Side Trips

Ilwaco, Long Beach, Cannon Beach, Chinook, Northwest Carriage Museum
Highlights from your plan
North Head Lighthouse ©
North Head Lighthouse
Cape Disappointment Lighthouse ©
Cape Disappointment Lighthouse
Lewis & Clark Interpretive Center ©
Lewis & Clark Interpretive Center

2
nights
Newport

Newport ©
A town that survives on the sea, Newport's population of just over 10,000 supports a healthy commercial fishing industry.
On the 19th (Thu), look for all kinds of wild species at Yaquina Head Outstanding Natural Area, enjoy the sea views from Yaquina Head Lighthouse, then take in the exciting artwork at The Edge Art Gallery, and finally examine the collection at Whale, Sea Life and Shark Museum. Keep things going the next day: take in the waterfront at Newport's Historic Bayfront, hike along Devils Punchbowl State Natural Area, and then kick back and relax at Nye Beach.

To see ratings, other places to visit, where to stay, and tourist information, use the Newport tour itinerary tool .

You can drive from Astoria to Newport in 3.5 hours. Alternatively, you can take a bus. Traveling from Astoria in September, expect nights in Newport to be about the same, around 50°F, while days are slightly colder, around 64°F. Finish your sightseeing early on the 20th (Fri) to allow enough time to drive to Florence.

Things to do in Newport

Parks Beaches Outdoors

Side Trips

Whale, Sea Life and Shark Museum, The Edge Art Gallery
Highlights from your plan
Nye Beach ©
Nye Beach
Yaquina Head Lighthouse ©
Yaquina Head Lighthouse
Yaquina Head Outstanding Natural Area ©

1
night
Florence

Florence ©
Florence is a coastal city in Lane County, in the U.S. On the 21st (Sat), cruise along Cape Perpetua Visitor Center - Siuslaw National Forest, then enjoy the sea views from Heceta Head Lighthouse, and then putt your heart out at Sandland Adventures.

To find reviews, more things to do, traveler tips, and more tourist information, use the Florence road trip planner .

You can drive from Newport to Florence in 1.5 hours. Another option is to take a bus. In September, daytime highs in Florence are 68°F, while nighttime lows are 52°F. Finish your sightseeing early on the 21st (Sat) so you can drive to Ashland.

Things to do in Florence

Nature Scenic Drive Outdoors

Side Trip

Cape Perpetua Visitor Center - Siuslaw National Forest
Highlights from your plan

4
nights
Ashland

Ashland ©
Ashland is a city in Jackson County, in the State of Oregon. Get a sense of the local culture at Chinese Cemetery Memorial and Franco American Hotel. Get out of town with these interesting Ashland side-trips: Siskiyou County Museum (in Yreka), Jedediah Smith Redwoods State Park (in Crescent City) and Crater Lake National Park (in Crater Lake National Park). And it doesn't end there: relax and float downstream with a rafting and tubing tour, stroll around Lithia Park, and catch a live performance at Oregon Shakespeare Festival.

For where to stay, reviews, other places to visit, and tourist information, go to the Ashland journey website .

Traveling by car from Florence to Ashland takes 4.5 hours. Alternatively, you can take a bus; or do a combination of bus and flight. When traveling from Florence in September, plan for somewhat warmer days in Ashland, with highs around 83°F, while nights are about the same with lows around 53°F. Finish your sightseeing early on the 25th (Wed) so you can drive to Bend.

Things to do in Ashland

Parks Nature Tours

Side Trips

Yreka, Jedediah Smith Redwoods State Park, Crater Lake National Park
Highlights from your plan
Crater Lake National Park ©
Crater Lake National Park
Siskiyou County Museum ©
Siskiyou County Museum
Franco American Hotel ©
Franco American Hotel

2
nights
Bend

Bend ©
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.
On the 26th (Thu), learn more about the world around you at High Desert Museum and then immerse yourself in nature at Smith Rock State Park.

To find ratings, reviews, photos, and tourist information, read Bend tour itinerary planner .

Drive from Ashland to Bend in 4.5 hours. Alternatively, you can do a combination of bus and flight; or take a bus. Plan for a bit cooler temperatures traveling from Ashland in September, with highs in Bend at 73°F and lows at 44°F. You will leave for home on the 27th (Fri).

Things to do in Bend

Parks Wildlife Museums

Side Trip

Smith Rock State Park
Highlights from your plan
High Desert Museum ©
High Desert Museum
Smith Rock State Park ©
Smith Rock State Park

Similar Plans

23 days in United States BY A USER FROM NETHERLANDS August, popular sights PREFERENCES: August ATTRACTION STYLE: Popular sights PACE: Medium 23 days in Oregon BY A USER FROM UNITED STATES September, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems PREFERENCES: September, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 5 days in Oregon BY A USER FROM UNITED STATES June, kids, outdoors, beaches, wildlife, popular sights PREFERENCES: June, kids, outdoors, beaches, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 36 days in United States BY A USER FROM UNITED STATES July, teens, kids, popular & hidden gems PREFERENCES: July, teens, kids ATTRACTION STYLE: Popular & hidden gems PACE: Medium 34 days in United States BY A USER FROM UNITED STATES July, teens, kids, popular sights PREFERENCES: July, teens, kids ATTRACTION STYLE: Popular sights PACE: Medium 41 days in Oregon BY A USER FROM UNITED STATES June, relaxing, romantic, beaches, shopping, wildlife, popular sights PREFERENCES: June, relaxing, romantic, beaches, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 3 days in Oregon BY A USER FROM UNITED STATES June, outdoors, beaches, historic sites, wildlife, popular sights PREFERENCES: June, outdoors, beaches, historic sites, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 11 days in Oregon BY A USER FROM UNITED STATES July, teens, kids, culture, outdoors, relaxing, beaches, historic sites, museums, wildlife, popular & hidden gems PREFERENCES: July, teens, kids, culture, outdoors, relaxing, beaches, historic sites, museums, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 15 days in Oregon BY A USER FROM UNITED STATES June, teens, kids, popular sights PREFERENCES: June, teens, kids ATTRACTION STYLE: Popular sights PACE: Medium 4 days in Oregon BY A USER FROM UNITED STATES July, kids, outdoors, relaxing, beaches, wildlife, popular & hidden gems PREFERENCES: July, kids, outdoors, relaxing, beaches, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 8 days in Oregon BY A USER FROM UNITED STATES July, outdoors, beaches, popular sights PREFERENCES: July, outdoors, beaches ATTRACTION STYLE: Popular sights PACE: Medium 4 days in Oregon BY A USER FROM UNITED STATES July, outdoors, beaches, wildlife, popular & hidden gems PREFERENCES: July, outdoors, beaches, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium
View more plans