49 days in Oregon Itinerary

Created using Inspirock Oregon planner
Make it your trip
Train to London Heathrow, Fly to Portland
1
Portland
— 5 nights
Drive
2
Hood River
— 5 nights
Fly
3
Bend
— 5 nights
Drive
4
Crater Lake National Park
— 4 nights
Drive
5
Ashland
— 4 nights
Drive
6
Eugene
— 5 nights
Drive
7
Florence
— 5 nights
Drive
8
Newport
— 4 nights
Drive
9
Tillamook
— 5 nights
Drive
10
Astoria
— 5 nights
+2
Bus to Sunset TC station, Fly to London Heathrow, Train to Exeter

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Portland — 5 nights

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.
Explore Portland's surroundings by going to Adventures Across Oregon - Guided Adventures to the 7 Wonders of Oregon (in Forest Grove), Evergreen Aviation & Space Museum (in McMinnville) and Multnomah Falls (in Bridal Veil). Dedicate the 8th (Thu) to wine at some of the top wineries in the area. The adventure continues: admire the natural beauty at Portland Japanese Garden, don't miss a visit to Pittock Mansion, steep yourself in history at Columbia River Highway, and hunt for treasures at Portland Saturday Market.

To see photos, other places to visit, more things to do, and other tourist information, refer to the Portland sightseeing planner.

Exeter, UK to Portland is an approximately 15-hour combination of train and flight. Due to the time zone difference, you'll gain 8 hours traveling from Exeter to Portland. In September, daytime highs in Portland are 28°C, while nighttime lows are 15°C. Finish up your sightseeing early on the 10th (Sat) so you can go by car to Hood River.
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Tours · Parks · Wineries · Outdoors
Side Trips
Find places to stay Sep 5 — 10:

Hood River — 5 nights

The city of Hood River is the seat of Hood River County, Oregon, United States. You'll find plenty of places to visit near Hood River: Hood River Winery Tours (in The Dalles), Government Camp (Timberline Lodge and Ski Area & Trillium Lake) and Cascade Locks (Eagle Creek Trail & Bonneville Lock & Dam). And it doesn't end there: contemplate the waterfront views at Columbia River Gorge National Scenic Area, delve into the lush surroundings at Mt. Hood National Forest, take an in-depth tour of Fort Dalles Museum and Anderson Homestead, and see the interesting displays at Western Antique Aeroplane & Automobile Museum.

For photos, maps, where to stay, and more tourist information, you can read our Hood River trip planning website.

You can drive from Portland to Hood River in 1.5 hours. Other options are to take a bus; or take a train. Traveling from Portland in September, you will find days in Hood River are little chillier (25°C), and nights are about the same (16°C). Finish up your sightseeing early on the 15th (Thu) so you can catch the flight to Bend.
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Parks · Nature · Outdoors · Museums
Side Trips
Find places to stay Sep 10 — 15:

Bend — 5 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.
Explore Bend's surroundings by going to Sisters (McKenzie Pass-Santiam Pass loop & Sahalie and Koosah Falls), Dee Wright Observatory (in Blue River) and Smith Rock State Park (in Redmond). There's still lots to do: get a new perspective on things with Boat Tours & Water Sports, walk around Drake Park, admire the sheer force of Tumalo Falls, and find your balance on the water with Bend River Attractions.

To find ratings, other places to visit, reviews, and more tourist information, you can read our Bend journey planner.

Getting from Hood River to Bend by flight takes about 2.5 hours. Other options: drive; or take a bus. Plan for a bit cooler nights when traveling from Hood River in September since evenings lows in Bend dip to 7°C. Finish up your sightseeing early on the 20th (Tue) so you can go by car to Crater Lake National Park.
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Parks · Nature · Outdoors · Tours
Side Trips
Find places to stay Sep 15 — 20:

Crater Lake National Park — 4 nights

Reaching a depth of 592 m (1,943 ft), Crater Lake is the deepest lake in the United States.
Spend the 21st (Wed) exploring nature at Crater Lake National Park. And it doesn't end there: explore and take pictures at Rim Dr, step off the mainland to explore Wizard Island, take a memorable drive along Rogue-Umpqua Scenic Byway, and trek along Sun Notch Trail.

For reviews, photos, traveler tips, and tourist information, use the Crater Lake National Park trip planner.

Traveling by car from Bend to Crater Lake National Park takes 2.5 hours. Alternatively, you can do a combination of bus and taxi. Plan for somewhat warmer temperatures traveling from Bend in September, with highs in Crater Lake National Park at 33°C and lows at 13°C. Cap off your sightseeing on the 24th (Sat) early enough to go by car to Ashland.
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Parks · Nature · Outdoors · Trails
Side Trips
Find places to stay Sep 20 — 24:

Ashland — 4 nights

Ashland is a city in Jackson County, in the State of Oregon. You'll find plenty of places to visit near Ashland: Medford (Natural Bridge Loop & Rogue River), Del Rio Vineyards & Winery (in Gold Hill) and Pacific Crest National Scenic Trail (in Dufur). There's lots more to do: take a tour by water with Boat Tours & Water Sports, catch a live performance at Oregon Shakespeare Festival, look for gifts at Bloomsbury Books, and identify plant and animal life at Wildlife Images - Rehabilitation & Education Center.

To see ratings, maps, reviews, and more tourist information, refer to the Ashland online tour planner.

Drive from Crater Lake National Park to Ashland in 2 hours. Alternatively, you can do a combination of taxi and bus. In September, plan for daily highs up to 33°C, and evening lows to 13°C. Finish up your sightseeing early on the 28th (Wed) so you can go by car to Eugene.
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Parks · Outdoors · Tours · Wineries
Side Trips
Find places to stay Sep 24 — 28:

Eugene — 5 nights

Eugene is a city of the Pacific Northwest located in the U.S. state of Oregon. Explore Eugene's surroundings by going to Willamette Valley Vineyards (in Turner), The Historic Carousel and Museum (in Albany) and Corvallis (Fitton Green Natural Area & 2 Towns Ciderhouse). And it doesn't end there: immerse yourself in nature at Thompson's Mill State Heritage Site, identify plant and animal life at Wildlife Safari, stroll around Spencer Butte, and make a trip to The Official Simpsons Mural.

To find where to stay, other places to visit, photos, and tourist information, refer to the Eugene trip builder site.

Drive from Ashland to Eugene in 3.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. Traveling from Ashland in September, expect nights in Eugene to be about the same, around 11°C, while days are little chillier, around 29°C. Cap off your sightseeing on the 3rd (Mon) early enough to go by car to Florence.
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Parks · Outdoors · Tours · Wildlife
Side Trips
Find places to stay Sep 28 — Oct 3:

Florence — 5 nights

Florence is a coastal city in Lane County, in the U.S. state of Oregon. Get out of town with these interesting Florence side-trips: Yachats (Cape Perpetua Visitor Center - Siuslaw National Forest & Devil's Churn), Bandon (Circles in the Sand, Bandon Dunes Golf Resort, &more) and Coos Bay (Cape Arago State Park & Shore Acres State Park). And it doesn't end there: visit a coastal fixture at Heceta Head Lighthouse, take in the views from Siuslaw River Bridge, take a memorable drive along Oregon Route 38, and enjoy some diversion at Sandland Adventures.

To find other places to visit, traveler tips, and tourist information, read Florence route maker tool.

You can drive from Eugene to Florence in 1.5 hours. Another option is to take a bus. In October, daily temperatures in Florence can reach 20°C, while at night they dip to 11°C. Wrap up your sightseeing on the 8th (Sat) early enough to drive to Newport.
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Parks · Outdoors · Nature · Scenic Drive
Side Trips
Find places to stay Oct 3 — 8:

Newport — 4 nights

A town that survives on the sea, Newport's population of just over 10,000 supports a healthy commercial fishing industry.
Explore the numerous day-trip ideas around Newport: Yachats coastline (in Yachats) and Lincoln City Glass Center (in Lincoln City). And it doesn't end there: observe the fascinating underwater world at Oregon Coast Aquarium, trek along Devils Punchbowl State Natural Area, identify plant and animal life at Yaquina Head Outstanding Natural Area, and visit a coastal fixture at Yaquina Head Lighthouse.

For photos, traveler tips, reviews, and other tourist information, you can read our Newport road trip planner.

You can drive from Florence to Newport in 1.5 hours. Alternatively, you can take a bus. In October, daytime highs in Newport are 18°C, while nighttime lows are 10°C. Cap off your sightseeing on the 12th (Wed) early enough to go by car to Tillamook.
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Parks · Outdoors · Nature · Wildlife
Side Trips
Find places to stay Oct 8 — 12:

Tillamook — 5 nights

The city of Tillamook is the county seat of Tillamook County, Oregon, United States. Get out of town with these interesting Tillamook side-trips: Cape Kiwanda State Natural Area (in Pacific City), Nehalem Bay State Park (in Nehalem) and Manzanita (Manzanita Beach & Short Sands Beach). Next up on the itinerary: admire the majestic nature at Oswald West State Park, take in the pleasant sights at Oceanside Beach State Recreation Site, take in the awesome beauty at Neahkahnie Mountain, and head outdoors with Netarts Bay.

To find maps, other places to visit, where to stay, and more tourist information, go to the Tillamook online travel planner.

Getting from Newport to Tillamook by car takes about 2 hours. Other options: take a bus. The time zone changes from Pacific Standard Time (PST) to Mountain Standard Time (MST), which is usually a 1 hour difference. Expect a daytime high around 20°C in October, and nighttime lows around 8°C. Wrap up your sightseeing on the 17th (Mon) to allow time to drive to Astoria.
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Parks · Outdoors · Beaches · Nature
Side Trips
Find places to stay Oct 12 — 17:

Astoria — 5 nights

Spirit of the Columbia

Astoria, named for famed fur trader John Jacob Astor, resides near the mouth of the Columbia River.
Get out of town with these interesting Astoria side-trips: Cannon Beach (Bronze Coast Gallery, Haystack Rock, &more) and Seaside (Turnaround at Seaside & Seaside Aquarium). The adventure continues: pause for some photo ops at Astoria Column, kick back and relax at Del Rey Beach State Recreation Site, contemplate the long history of Lewis & Clark Salt Works, and see the interesting displays at Flavel House Museum.

To find photos, where to stay, ratings, and tourist information, read Astoria trip maker app.

You can drive from Tillamook to Astoria in 2 hours. Another option is to take a bus. Due to the time zone difference, you'll gain 1 hour traveling from Tillamook to Astoria. In October, daily temperatures in Astoria can reach 20°C, while at night they dip to 10°C. Finish your sightseeing early on the 22nd (Sat) so you can travel back home.
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Parks · Nature · Historic Sites · Museums
Side Trips
Find places to stay Oct 17 — 22:

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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