60 days in Oregon Itinerary

Created using Inspirock Oregon trip builder
Make it your trip
Fly
1
Bend
— 5 nights
Fly
2
Hood River
— 6 nights
Drive
3
Portland
— 9 nights
Drive
4
Astoria
— 7 nights
Drive
5
Newport
— 7 nights
Drive
6
Florence
— 6 nights
Drive
7
Coos Bay
— 6 nights
Drive
8
Grants Pass
— 6 nights
Drive
9
Eugene
— 7 nights
Fly

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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 (The Collection Gallery, Hoodoo Ski Area, &more), Smith Rock State Park (in Redmond) and Bowman Museum (in Prineville). There's lots more to do: see the interesting displays at High Desert Museum, contemplate the waterfront views at Deschutes River, wander the wide-open spaces of Brasada Ranch, and stroll through Mt. Bachelor Ski Area.

To find where to stay, other places to visit, reviews, and tourist information, refer to the Bend trip planning tool.

Los Angeles to Bend is an approximately 4-hour flight. You can also drive; or take a bus. In December, Bend is much colder than Los Angeles - with highs of 40°F and lows of 22°F. Wrap up your sightseeing on the 6th (Tue) to allow time to fly to Hood River.
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Parks · Outdoors · Winter Sports · Museums
Side Trips

Hood River — 6 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: Government Camp (Little Zigzag Falls, Trillium Lake, &more), Bonneville Lock & Dam (in Cascade Locks) and Mt. Hood Meadows (in Parkdale). The adventure continues: contemplate the waterfront views at Columbia River Gorge National Scenic Area, delve into the lush surroundings at Starvation Creek Ridge Loop, see the interesting displays at Western Antique Aeroplane & Automobile Museum, and tour the pleasant surroundings at Historic Columbia River Highway State Trail.

Planning Hood River trip won't be overwhelming when you use Inspirock's itinerary maker.

You can fly from Bend to Hood River in 2.5 hours. Alternatively, you can drive; or take a bus. Traveling from Bend in December, Hood River is a bit warmer at night with lows of 30°F. Finish your sightseeing early on the 12th (Mon) to allow enough time to drive to Portland.
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Parks · Outdoors · Winter Sports · Nature
Side Trips

Portland — 9 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.
Change things up with these side-trips from Portland: Salem's Riverfront Carousel (in Salem), Multnomah Falls (in Bridal Veil) and Sokol Blosser Tasting Room & Winery (in Dundee). There's much more to do: look for gifts at Powell's City of Books, admire the natural beauty at Portland Japanese Garden, make a trip to Pittock Mansion, and admire nature's wide array of creatures at Oregon Zoo.

To see more things to do, traveler tips, other places to visit, and other tourist information, use the Portland route planning website.

Traveling by car from Hood River to Portland takes 1.5 hours. Alternatively, you can take a bus; or take a train. In December in Portland, expect temperatures between 45°F during the day and 35°F at night. Finish up your sightseeing early on the 21st (Wed) so you can go by car to Astoria.
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Parks · Museums · Outdoors · Nature
Side Trips

Astoria — 7 nights

Spirit of the Columbia

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 (Tillamook Rock Light, Ecola State Park, &more), Cape Meares Lighthouse (in Tillamook) and Seaside (Turnaround at Seaside & Seaside Aquarium). Spend the 25th (Sun) exploring nature at Fort Clatsop National Memorial. Next up on the itinerary: immerse yourself in nature at Fort Stevens State Park, see the interesting displays at Seaside Inverted Experience, appreciate the history behind Astoria Column, and walk around Tapiola Park.

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

Traveling by car from Portland to Astoria takes 2 hours. Alternatively, you can take a bus. In December, daytime highs in Astoria are 49°F, while nighttime lows are 37°F. Cap off your sightseeing on the 28th (Wed) early enough to go by car to Newport.
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Parks · Nature · Historic Sites · Outdoors
Side Trips

Newport — 7 nights

A town that survives on the sea, Newport's population of just over 10,000 supports a healthy commercial fishing industry.
Change things up with these side-trips from Newport: Beachcrest Brewing Company (in Gleneden Beach), Lincoln City (Rock Your World: Pacific Northwest Gem & Jewelry Gallery, Chinook Winds Casino & Convention Center, &more) and Yachats (Yachats coastline & Bazalgette the Whale at Whale Park). There's still lots to do: get up close and personal with brilliant marine life at Oregon Coast Aquarium, take a leisurely stroll along Newport's Historic Bayfront, walk around Governor Patterson Memorial State Recreation Site, and enjoy the sand and surf at Nye Beach.

To see reviews, maps, and more tourist information, read our Newport travel app.

You can drive from Astoria to Newport in 3.5 hours. Another option is to take a bus. In December, daytime highs in Newport are 49°F, while nighttime lows are 39°F. Wrap up your sightseeing on the 4th (Wed) early enough to drive to Florence.
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Parks · Nature · Beaches · Outdoors
Side Trips

Florence — 6 nights

Florence is a coastal city in Lane County, in the U.S. state of Oregon. Venture out of the city with trips to Yachats (Devil's Churn & Cape Perpetua Visitor Center - Siuslaw National Forest) and Reedsport (Umpqua Discovery Center & Mindpower Gallery). The adventure continues: catch some excitement at Sandland Adventures, enjoy the sea views from Heceta Head Lighthouse, cruise along Oregon Coast Hwy, and see the interesting displays at Siuslaw Pioneer Museum.

For where to stay, other places to visit, more things to do, and tourist information, read our Florence trip planner.

Traveling by car from Newport to Florence takes 1.5 hours. Alternatively, you can take a bus. January in Florence sees daily highs of 55°F and lows of 40°F at night. Finish your sightseeing early on the 10th (Tue) so you can drive to Coos Bay.
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Outdoors · Parks · Nature · Golf
Side Trips

Coos Bay — 6 nights

Coos Bay is a city located in Coos County, Oregon, United States, where the Coos River enters Coos Bay on the Pacific Ocean. Venture out of the city with trips to Bandon (Coquille River Lighthouse, Circles in the Sand, &more). And it doesn't end there: admire the majestic nature at Shore Acres State Park, make a trip to Steve Prefontaine Murals, get up close and personal with brilliant marine life at Charleston Marine Life Center, and play a few rounds at Bandon Dunes Golf Resort.

For photos, more things to do, reviews, and other tourist information, use the Coos Bay trip website.

Drive from Florence to Coos Bay in 1.5 hours. In January, daily temperatures in Coos Bay can reach 55°F, while at night they dip to 40°F. Wrap up your sightseeing on the 16th (Mon) early enough to drive to Grants Pass.
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Parks · Outdoors · Golf · Nature
Side Trips

Grants Pass — 6 nights

Grants Pass is a city in, and the county seat of, Josephine County, Oregon, United States. Explore Grants Pass' surroundings by going to Ashland (Gathering Glass Studio, Lithia Park, &more), Brookings (Azalea Park & Secret Beach) and Crater Lake National Park (in Crater Lake National Park). There's lots more to do: take in the exciting artwork at The Glass Forge, relax and rejuvenate at Angelica Day Spa & Boutique, look for gifts at Rogue Creamery, and take in the views from The Wimer Covered Bridge.

To find reviews, ratings, other places to visit, and tourist information, you can read our Grants Pass trip planner.

You can drive from Coos Bay to Grants Pass in 3 hours. Traveling from Coos Bay in January, expect Grants Pass to be a bit cooler, temps between 43°F and 34°F. Wrap up your sightseeing on the 22nd (Sun) early enough to drive to Eugene.
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Parks · Nature · Museums · Shopping
Side Trips

Eugene — 7 nights

Eugene is a city of the Pacific Northwest located in the U.S. state of Oregon. Get out of town with these interesting Eugene side-trips: Albany (Albany Antique Mall, The Historic Carousel and Museum, &more), Roseburg (Melrose Vineyards & Two Shy Brewing) and Corvallis (The Arts Center, 2 Towns Ciderhouse, &more). There's still lots to do: look for all kinds of wild species at Cascades Raptor Center, walk around Pre's Trail, look for gifts at Oregon Wine Lab, and admire the masterpieces at Jordan Schnitzer Museum of Art.

To see photos, traveler tips, where to stay, and tourist information, go to the Eugene vacation tool.

You can drive from Grants Pass to Eugene in 2.5 hours. In January in Eugene, expect temperatures between 47°F during the day and 34°F at night. Finish your sightseeing early on the 29th (Sun) to allow enough time to fly back home.
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Parks · Wineries · Museums · Shopping
Side Trips

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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