56 days in Oregon Itinerary

56 days in Oregon Itinerary

Created using Inspirock Oregon tour builder

Plan created by another user. Make it yours
Fly
1
Cannon Beach
— 6 nights
Drive
2
Newport
— 7 nights
Drive
3
Florence
— 6 nights
Drive
4
Bandon
— 6 nights
Drive
5
Crater Lake National Park
— 5 nights
Drive
6
Bend
— 7 nights
Drive
7
Timberline Lodge
— 6 nights
Drive
8
Portland
— 12 nights
Fly

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6
nights
Cannon Beach

Cannon Beach is a city in Clatsop County, Oregon, United States. Relax by the water at Haystack Rock and Tolovana Beach State Recreation Site. Visit Fort Clatsop National Memorial and Tillamook Rock Light for their historical value. Get out of town with these interesting Cannon Beach side-trips: Astoria (Astoria Column, Columbia River Maritime Museum, &more), Tillamook (Tillamook Air Museum, Cape Meares Lighthouse, &more) and Rockaway Beach Wayside (in Rockaway Beach). There's still lots to do: admire the majestic nature at Ecola State Park, enjoy the sand and surf at Manzanita Beach, stop by Beach Books, and stroll through Cannon Beach.

To find photos, maps, reviews, and other tourist information, read Cannon Beach trip itinerary app.

New York City to Cannon Beach is an approximately 12-hour flight. You can also drive; or do a combination of train and bus. You'll gain 3 hours traveling from New York City to Cannon Beach due to the time zone difference. In May, Cannon Beach is slightly colder than New York City - with highs of 62°F and lows of 48°F. Finish your sightseeing early on the 5th (Wed) so you can drive to Newport.

Things to do in Cannon Beach

Parks · Nature · Beaches · Historic Sites

Side Trips

7
nights
Newport

A town that survives on the sea, Newport's population of just over 10,000 supports a healthy commercial fishing industry.
Appreciate the collections at Lincoln City Glass Center and The Historic Carousel and Museum. Head to Newport Farmer's Market and The Chocolate Frogfor plenty of shopping. Change things up with these side-trips from Newport: Left Coast Estate (in Rickreall), Airlie Winery (in Monmouth) and Yachats (Yachats coastline & Cape Perpetua Visitor Center - Siuslaw National Forest). And it doesn't end there: identify plant and animal life at Yaquina Head Outstanding Natural Area, enjoy the sea views from Yaquina Head Lighthouse, take in the dramatic natural features at Cape Foulweather, and kick back and relax at Fogarty Creek State Recreation Area.

For photos, reviews, other places to visit, and more tourist information, go to the Newport trip itinerary website.

You can drive from Cannon Beach to Newport in 3 hours. Alternatively, you can take a bus. When traveling from Cannon Beach in June, plan for slightly colder days in Newport, with highs around 61°F, while nights are about the same with lows around 48°F. Finish your sightseeing early on the 12th (Wed) to allow enough time to drive to Florence.

Things to do in Newport

Parks · Outdoors · Nature · Beaches

Side Trips

6
nights
Florence

Florence is a coastal city in Lane County, in the U.S. Get some cultural insight at Heceta Head Lighthouse and Lane County History Museum. Get outdoors at Sandland Adventures and Sea Lion Caves. Explore the numerous day-trip ideas around Florence: Dean Creek Elk Viewing Area (in Reedsport), Umpqua Triangle Oyster from Aquaculture (in Winchester Bay) and Eugene (Cascades Raptor Center, Shelton McMurphey Johnson House, &more). The adventure continues: get outside with Sand Master Park - Sandboarding, snap pictures at Lowell Bridge, admire the majestic nature at William M. Tugman State Park, and tour the pleasant surroundings at Heceta Beach.

To find where to stay, photos, traveler tips, and tourist information, refer to the Florence trip maker tool.

You can drive from Newport to Florence in 1.5 hours. Alternatively, you can take a bus. In June, plan for daily highs up to 65°F, and evening lows to 52°F. Cap off your sightseeing on the 18th (Tue) early enough to go by car to Bandon.

Things to do in Florence

Parks · Nature · Outdoors · Wildlife

Side Trips

6
nights
Bandon

Bandon is a city in Coos County, Oregon, United States, on the south side of the mouth of the Coquille River. Do some cultural sightseeing at Coquille River Lighthouse and Reustle Prayer Rock Vineyards. You'll get in some beach time at Coquille Point and Ophir Beach. Get out of town with these interesting Bandon side-trips: Paul O'Brien Winery (in Roseburg), Wildlife Safari (in Winston) and Coos Bay (Cape Arago State Park & Shore Acres State Park). Next up on the itinerary: take in the dramatic natural features at Face Rock State Scenic Viewpoint, look for all kinds of wild species at West Coast Game Park Safari, tee off at Bandon Dunes Golf Resort, and stop by Langlois Market.

To find maps, reviews, other places to visit, and more tourist information, you can read our Bandon tour itinerary maker tool.

Drive from Florence to Bandon in 1.5 hours. Alternatively, you can take a bus. Expect a daytime high around 65°F in June, and nighttime lows around 52°F. Finish up your sightseeing early on the 24th (Mon) so you can go by car to Crater Lake National Park.

Things to do in Bandon

Parks · Outdoors · Nature · Beaches

Side Trips

5
nights
Crater Lake National Park

Reaching a depth of 592 m (1,943 ft), Crater Lake is the deepest lake in the United States.
Do some cultural sightseeing at The Glass Forge and Wooldridge Creek Winery. Get outdoors at Crater Lake National Park and Wildlife Images - Rehabilitation & Education Center. Venture out of the city with trips to Grants Pass (Bear Hotel Artworks Museum & Schmidt Family Vineyards), Ashland (Oregon Shakespeare Festival & Schneider Museum of Art) and Rogue River (in Medford). There's much more to do: hike along Garfield Peak, stop by Rogue Creamery, learn about winemaking at LongSword Vineyard, and head off the coast to Wizard Island.

For other places to visit, maps, more things to do, and other tourist information, read Crater Lake National Park trip site.

Getting from Bandon to Crater Lake National Park by car takes about 5 hours. Other options: do a combination of bus, train, and taxi; or do a combination of bus and taxi. Traveling from Bandon in June, expect nights in Crater Lake National Park to be about the same, around 55°F, while days are much hotter, around 86°F. Finish your sightseeing early on the 29th (Sat) to allow enough time to drive to Bend.

Things to do in Crater Lake National Park

Parks · Nature · Wineries · Outdoors

Side Trips

7
nights
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.
Step out of the city life by going to Smith Rock State Park and Deschutes National Forest. Shop till you drop at Cowgirl Cash and The Village at Sunriver. You'll find plenty of places to visit near Bend: Sisters (Sahalie and Koosah Falls, McKenzie Pass-Santiam Pass loop, &more), Tumalo Mountain (in Redmond) and Brasada Ranch (in Powell Butte). The adventure continues: see the interesting displays at High Desert Museum, explore the activities along Hosmer Lake, admire the sheer force of Tumalo Falls, and Head underground at Lava River Cave.

To find more things to do, traveler tips, where to stay, and other tourist information, read our Bend day trip app.

Getting from Crater Lake National Park to Bend by car takes about 2.5 hours. Other options: do a combination of taxi and bus. Traveling from Crater Lake National Park in June, things will get a bit cooler in Bend: highs are around 75°F and lows about 45°F. Finish up your sightseeing early on the 6th (Sat) so you can travel to Timberline Lodge.

Things to do in Bend

Parks · Nature · Museums · Scenic Drive

Side Trips

6
nights
Timberline Lodge

Perched high on the south face of one of the most iconic peaks in the Pacific Northwest, Timberline Lodge is the ski and snowboarding area known for the eponymous historic lodge, the design of which emphasizes the area's natural beauty.
Your cultural itinerary includes sights like Timberline Lodge and Ski Area and Western Antique Aeroplane & Automobile Museum. Get outdoors at Columbia River Gorge National Scenic Area and Mount Hood. You'll find plenty of places to visit near Timberline Lodge: Historic Columbia River Highway State Trail (in Mosier), Columbia Gorge Discovery Center & Museum (in The Dalles) and White Salmon River (in Hood River). There's lots more to do: look for all kinds of wild species at Wildwood Recreation Site, contemplate the waterfront views at Trillium Lake, trek along Little Zigzag Falls, and take in the dramatic scenery at Ramona Falls Trail.

To see ratings, reviews, where to stay, and other tourist information, you can read our Timberline Lodge day trip planning site.

Traveling by car from Bend to Timberline Lodge takes 2.5 hours. Traveling from Bend in July, expect nights in Timberline Lodge to be somewhat warmer, around 58°F, while days are slightly colder, around 79°F. Cap off your sightseeing on the 12th (Fri) early enough to go by car to Portland.

Things to do in Timberline Lodge

Parks · Nature · Outdoors · Trails

Side Trips

12
nights
Portland

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.
Popular historic sites such as Columbia River Highway and The Oregon Garden are in your itinerary. Do some cultural sightseeing at Oregon Museum of Science and Industry and Eastbank Esplanade. Explore Portland's surroundings by going to Carlton (Carlton Winemakers Studio & Soter Vineyards), Elk Cove Vineyards (in Gaston) and St. Mary's Catholic Church (in Mount Angel). Next up on the itinerary: stop by Powell's City of Books, examine the collection at Portland Art Museum, learn about winemaking at Willamette Valley Vineyards, and head outdoors with Portland Timbers.

To see photos, maps, reviews, and other tourist information, go to the Portland online journey planner.

Traveling by car from Timberline Lodge to Portland takes 1.5 hours. July in Portland sees daily highs of 83°F and lows of 59°F at night. You'll have a few hours on the 24th (Wed) to wrap things up before traveling home.

Things to do in Portland

Parks · Wineries · Nature · 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.