56 days in Oregon Itinerary

56 days in Oregon Itinerary

Created using Inspirock Oregon tour builder

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Route & dates

56 days in Oregon Itinerary

Start: New York City
+3
bus + Fly + tram + bus:  12​h
1
Cannon Beach
— 6 nights
Drive:  2​h 45​min
2
Newport
— 7 nights
Drive:  1​h 15​min
3
Florence
— 6 nights
Drive:  2​h
4
Bandon
— 6 nights
Drive:  4​h 45​min
5
Crater Lake National Park
— 5 nights
Drive:  2​h 45​min
6
Bend
— 7 nights
Drive:  2​h 30​min
7
Timberline Lodge
— 6 nights
Drive:  1​h 30​min
8
Portland
— 12 nights
Fly + foot:  8​h 45​min
End: New York City

6
nights
Cannon Beach

Cannon Beach ©
Cannon Beach is a city in Clatsop County, Oregon, United States. Take a break from the city and head to Haystack Rock and Fort Clatsop National Memorial. Your itinerary includes some good beach time at Cannon Beach and Manzanita Beach. Change things up with these side-trips from Cannon Beach: Astoria (Astoria Column, Columbia River Maritime Museum, & more), Tillamook (Tillamook Air Museum, Cape Meares Lighthouse, & more) and Rockaway Beach Wayside (in Rockaway Beach). And it doesn't end there: admire the majestic nature at Ecola State Park, kick back and relax at Tolovana Beach State Recreation Site, stop by Beach Books, and visit a coastal fixture at Tillamook Rock Light.

For more things to do, photos, reviews, and other tourist information, use the Cannon Beach attractions planner.

New York City to Cannon Beach is an approximately 12-hour combination of bus and flight. You can also do a combination of flight and bus; or drive. The time zone difference when traveling from New York City to Cannon Beach is minus 3 hours. Traveling from New York City in May, things will get slightly colder in Cannon Beach: highs are around 62°F and lows about 48°F. Finish your sightseeing early on the 5th (Wed) to allow enough time to drive to Newport.

Things to do in Cannon Beach

Parks Nature Beaches

Side Trips

Astoria, Tillamook, Beach Books, Nehalem Bay State Park, Manzanita Beach
Highlights from your plan
Haystack Rock ©
Haystack Rock
Cannon Beach ©
Cannon Beach
Ecola State Park ©
Ecola State Park

7
nights
Newport

Newport ©
A town that survives on the sea, Newport's population of just over 10,000 supports a healthy commercial fishing industry.
Visiting Cape Perpetua Visitor Center - Siuslaw National Forest and Nye Beach will get you outdoors. You'll explore and learn at Lincoln City Glass Center and Hatfield Marine Science Center. Venture out of the city with trips to Airlie Winery (in Monmouth), Yachats coastline (in Yachats) and The Historic Carousel and Museum (in Albany). The adventure continues: identify plant and animal life at Yaquina Head Outstanding Natural Area, learn about winemaking at Left Coast Cellars, kick back and relax at Fogarty Creek State Recreation Area, and enjoy the sea views from Yaquina Head Lighthouse.

To find reviews, more things to do, other places to visit, and other tourist information, you can read our Newport trip planner .

Traveling by car from Cannon Beach to Newport takes 3 hours. Alternatively, you can take a bus. Traveling from Cannon Beach in June, you will find days in Newport are little chillier (61°F), and nights are about the same (48°F). Wrap up your sightseeing on the 12th (Wed) early enough to drive to Florence.

Things to do in Newport

Parks Outdoors Nature

Side Trips

Depoe Bay, Yachats, William L. Finley National Wildlife Refuge, Mike Miller Park, The Historic Carousel and Museum
Highlights from your plan

6
nights
Florence

Florence ©
Florence is a coastal city in Lane County, in the U.S. Step out of the city life by going to Heceta Beach and Sea Lion Caves. Satisfy your inner culture vulture at Heceta Head Lighthouse and Shelton-McMurphey-Johnson House. You'll find plenty of places to visit near Florence: Umpqua Aquaculture Triangle Oyster Farm (in Winchester Bay), Eugene (Cascades Raptor Center, Eugene Saturday Market, & more) and Dean Creek Elk Viewing Area (in Reedsport). The adventure continues: have fun at Sand Master Park, immerse yourself in nature at William M. Tugman State Park, snap pictures at Lowell Bridge, and try for a hole-in-one at Sandland Adventures.

To see maps and tourist information, use the Florence trip tool .

Traveling by car from Newport to Florence takes 1.5 hours. Alternatively, you can do a combination of bus and taxi. In June, daily temperatures in Florence can reach 65°F, while at night they dip 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

Side Trips

Eugene, William M. Tugman State Park, Umpqua Aquaculture Triangle Oyster Farm, Lowell Bridge, Dean Creek Elk Viewing Area
Highlights from your plan
Heceta Beach ©
Heceta Beach
Heceta Head Lighthouse ©
Heceta Head Lighthouse
Cascades Raptor Center ©
Cascades Raptor Center

6
nights
Bandon

Bandon ©
Bandon is a city in Coos County, Oregon, United States, on the south side of the mouth of the Coquille River. Get in touch with nature at Face Rock State Scenic Viewpoint and Lone Ranch Beach. Relax by the water at Coquille Point and Whiskey Run Beach. Explore Bandon's surroundings by going to Wildlife Safari (in Winston), Coos Bay (Cape Arago State Park & Shore Acres State Park) and Roseburg (Paul O'Brien Winery & Reustle Prayer Rock Vineyards). Next up on the itinerary: enjoy the sea views from Coquille River Lighthouse, immerse yourself in nature at Port Orford Heads State Park, look for gifts at Misty Meadows Jams, and look for all kinds of wild species at West Coast Game Park Safari.

For traveler tips, where to stay, and other tourist information, you can read our Bandon travel itinerary planner.

Drive from Florence to Bandon in 2 hours. Alternatively, you can take a bus. In June in Bandon, expect temperatures between 65°F during the day and 52°F at night. Wrap up your sightseeing on the 24th (Mon) early enough to drive to Crater Lake National Park.

Things to do in Bandon

Parks Outdoors Nature

Side Trips

Roseburg, Port Orford, Coos Bay, Lone Ranch Beach, Langlois Market
Highlights from your plan
Shore Acres State Park ©
Shore Acres State Park
Face Rock State Scenic Viewpoint ©
Face Rock State Scenic Viewpoint
Wildlife Safari ©
Wildlife Safari

5
nights
Crater Lake National Park

Crater Lake National Park ©
Reaching a depth of 592 m (1,943 ft), Crater Lake is the deepest lake in the United States.
Escape the urban bustle at Crater Lake National Park and Wildlife Images - Rehabilitation & Education Center. Wooldridge Creek Winery and Rim Village Visitor Center are good opportunities to explore the local culture. Venture out of the city with trips to Grants Pass (The Glass Forge, Bear Hotel Artworks Museum, & more), Rogue River (in Medford) and Ashland (Oregon Shakespeare Festival & Schneider Museum of Art). There's lots more to do: hike along Garfield Peak, step off the mainland to explore Wizard Island, stop by Rogue Creamery, and do a tasting at LongSword Vineyard.

To see traveler tips, photos, other places to visit, and more tourist information, you can read our Crater Lake National Park online trip planner .

Traveling by car from Bandon to Crater Lake National Park takes 5 hours. Alternatively, you can do a combination of bus, train, and taxi; or do a combination of bus and taxi. When traveling from Bandon in June, plan for much hotter days in Crater Lake National Park, with highs around 86°F, while nights are about the same with lows around 55°F. Cap off your sightseeing on the 29th (Sat) early enough to go by car to Bend.

Things to do in Crater Lake National Park

Parks Nature Wineries

Side Trips

Grants Pass, Ashland, Rogue River, Rogue Creamery, LongSword Vineyard
Highlights from your plan
The Glass Forge ©
The Glass Forge
Crater Lake National Park ©
Crater Lake National Park
Oregon Shakespeare Festival ©
Oregon Shakespeare Festival

7
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.
Visiting High Desert Museum and Deschutes River will get you outdoors. Venture out of the city with trips to Sisters (Sahalie and Koosah Falls & McKenzie Pass-Santiam Pass loop), Brasada Ranch (in Powell Butte) and Redmond (Smith Rock State Park & Tumalo Mountain). There's lots more to do: delve into the lush surroundings at Deschutes National Forest, contemplate the waterfront views at Hosmer Lake, take a stroll through City of Sisters, and take in the dramatic scenery at Tumalo Falls.

Plan my trip to Bend with suggested itineraries provided by Inspirock.

You can drive from Crater Lake National Park to Bend in 3 hours. Alternatively, you can do a combination of taxi and bus. In June, Bend is little chillier than Crater Lake National Park - with highs of 75°F and lows of 45°F. Cap off your sightseeing on the 6th (Sat) early enough to travel to Timberline Lodge.

Things to do in Bend

Parks Nature Wildlife

Side Trips

Sisters, Redmond, The Village at Sunriver, East Lake, Brasada Ranch
Highlights from your plan
High Desert Museum ©
High Desert Museum
Smith Rock State Park ©
Smith Rock State Park
Deschutes National  Forest ©
Deschutes National Forest

6
nights
Timberline Lodge

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.
Escape the urban bustle at Timberline Lodge and Ski Area and Mt. Hood National Forest. Museum-lovers will appreciate Western Antique Aeroplane & Automobile Museum and Columbia Gorge Discovery Center & Museum. Change things up with these side-trips from Timberline Lodge: White Salmon River (in Hood River) and Historic Columbia River Highway State Trail (in Mosier).

To see ratings, other places to visit, maps, and more tourist information, read Timberline Lodge sightseeing planner .

Drive from Bend to Timberline Lodge in 2.5 hours. Expect little chillier weather when traveling from Bend in July: highs in Timberline Lodge hover around 79°F, while lows dip to 58°F. Finish your sightseeing early on the 12th (Fri) to allow enough time to travel to Portland.

Things to do in Timberline Lodge

Nature Parks Outdoors

Side Trips

Hood River, Government Camp, Oregon, Wildwood Recreation Site, Columbia Gorge Discovery Center & Museum
Highlights from your plan

12
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.
Museum-lovers will appreciate Evergreen Aviation & Space Museum and Oregon Maritime Museum. Get outdoors at Multnomah Falls and Oregon Zoo. Explore the numerous day-trip ideas around Portland: Carlton (Carlton Winemakers Studio & Soter Vineyards), Elk Cove Vineyards (in Gaston) and St. Mary's Catholic Church (in Mount Angel). There's lots more to do: look for gifts at Powell's City of Books, indulge your taste buds at Sokol Blosser Winery, hunt for treasures at Portland Saturday Market, and steep yourself in history at Pittock Mansion.

To see photos, traveler tips, and tourist information, read Portland itinerary planner .

Drive from Timberline Lodge to Portland in 1.5 hours. Expect a daytime high around 83°F in July, and nighttime lows around 59°F. On the 24th (Wed), you'll have the morning to explore before heading back home.

Things to do in Portland

Parks Wineries Nature

Side Trips

Silverton, Dundee, Carlton, Dayton, Bush's Pasture Park
Highlights from your plan
Powell's City of Books ©
Powell's City of Books
Evergreen Aviation & Space Museum ©
Evergreen Aviation & Space Museum
Multnomah Falls ©
Multnomah Falls

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