56 days in Oregon Itinerary

56 days in Oregon Itinerary

Created using Inspirock Oregon tour builder

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

S M T W T F S
26
27
28
29
30
31
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27

6
nights
Cannon Beach

Cannon Beach ©
Cannon Beach is a city in Clatsop County, Oregon, United States. Relax by the water at Haystack Rock and Manzanita Beach. Visit Fort Clatsop National Memorial and Tillamook Rock Light for their historical value. Get out of town with these interesting Cannon Beach side-trips: Rockaway Beach Wayside (in Rockaway Beach), Astoria (Astoria Column, Columbia River Maritime Museum, &more) and Tillamook (Tillamook Air Museum, Cape Meares Lighthouse, &more). The adventure continues: admire the majestic nature at Ecola State Park, take in the exciting artwork at Bronze Coast Gallery, look for gifts at Beach Books, and enjoy the sand and surf at Cannon Beach.

For photos, maps, traveler tips, and other tourist information, go to the Cannon Beach trip planning tool.

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. Expect slightly colder temperatures when traveling from New York City in May; daily highs in Cannon Beach reach 62°F and lows reach 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 · Outdoors · Beaches

Side Trips

Highlights from your trip
©
Must see
Haystack Rock
4.8
©
Must see
Cannon Beach
4.8
©
Must see
Ecola State Park
4.8

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.
Appreciate the collections at Lincoln City Glass Center and Hatfield Marine Science Center. Head to Newport Farmer's Market and Ainslee's Salt Water Taffyfor plenty of shopping. Change things up with these side-trips from Newport: Airlie Winery (in Monmouth), Yachats (Yachats coastline & Cape Perpetua Visitor Center - Siuslaw National Forest) and The Historic Carousel and Museum (in Albany). 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, get up close and personal with brilliant marine life at Oregon Coast Aquarium, and kick back and relax at Nye Beach.

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

Highlights from your trip

6
nights
Florence

Florence ©
Florence is a coastal city in Lane County, in the U.S. Get some cultural insight at Heceta Head Lighthouse and Shelton McMurphey Johnson House. 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, Eugene Saturday Market, &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

Highlights from your trip
©
Beach
Heceta Beach
4.7
©
Ride / Activity
Sandland Adventures
4.7

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. Do some cultural sightseeing at Coquille River Lighthouse and Reustle Prayer Rock Vineyards. You'll get in some beach time at Coquille Point and Lone Ranch 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). There's still lots to do: take in the dramatic natural features at Face Rock State Scenic Viewpoint, identify plant and animal life at West Coast Game Park Safari, enjoy the sand and surf at Ophir Beach, and stop by Misty Meadows Jams.

To find where to stay, maps, traveler tips, and tourist information, use the Bandon trip planner.

You can drive from Florence to Bandon in 1.5 hours. Another option is to take a bus. June in Bandon sees daily highs of 65°F and lows of 52°F at night. 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

Highlights from your trip
©
Geologic Formation
Face Rock State Scenic Viewpoint
4.8
©
Wildlife Area
Wildlife Safari
4.5

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.
Do some cultural sightseeing at The Glass Forge and Bear Hotel Artworks Museum. Get outdoors at Crater Lake National Park and Rogue River. Venture out of the city with trips to Ashland (Oregon Shakespeare Festival & Schneider Museum of Art), LongSword Vineyard (in Jacksonville) and Grants Pass (Wildlife Images - Rehabilitation & Education Center, Wooldridge Creek Winery, &more). There's much more to do: hike along Garfield Peak, steep yourself in history at Rim Village Visitor Center, step off the mainland to explore Wizard Island, and look for gifts at Rogue Creamery.

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 · Trails

Side Trips

Highlights from your trip

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.
Step out of the city life by going to Smith Rock State Park and Lava River Cave. Shop till you drop at Cowgirl Cash and The Village at Sunriver. You'll find plenty of places to visit near Bend: Brasada Ranch (in Powell Butte), Tumalo Mountain (in Redmond) and Sisters (Sahalie and Koosah Falls, McKenzie Pass-Santiam Pass loop, &more). There's lots more to do: see the interesting displays at High Desert Museum, explore the activities along Hosmer Lake, take in the dramatic scenery at Tumalo Falls, and stroll around Drake Park.

For traveler tips, ratings, where to stay, and more tourist information, use the Bend online route planner.

You can drive from Crater Lake National Park to Bend in 3 hours. Alternatively, you can do a combination of taxi and bus. Plan for slightly colder temperatures traveling from Crater Lake National Park in June, with highs in Bend at 75°F and lows at 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

Highlights from your trip
©
Specialty Museum
High Desert Museum
4.7

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.
Your cultural itinerary includes sights like Timberline Lodge and Ski Area and Columbia Gorge Discovery Center & Museum. Get outdoors at Columbia River Gorge National Scenic Area and Wildwood Recreation Site. You'll find plenty of places to visit near Timberline Lodge: Historic Columbia River Highway State Trail (in Mosier) and Hood River (Western Antique Aeroplane & Automobile Museum & White Salmon River). There's still lots to do: get impressive views of Mount Hood, take in the dramatic scenery at Ramona Falls Trail, explore and take pictures at Hood River County Fruit Loop, and identify plant and animal life at Little Zigzag Falls.

To find other places to visit, maps, and tourist information, you can read our Timberline Lodge trip itinerary app.

Traveling by car from Bend to Timberline Lodge takes 2.5 hours. Traveling from Bend in July, you will find days in Timberline Lodge are slightly colder (79°F), and nights are somewhat warmer (58°F). Wrap up your sightseeing on the 12th (Fri) early enough to drive to Portland.

Things to do in Timberline Lodge

Parks · Nature · Outdoors · Trails

Side Trips

Highlights from your trip

12
nights
Portland

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 St. Mary's Catholic Church are in your itinerary. Do some cultural sightseeing at Oregon Museum of Science and Industry and Portland Art Museum. Explore Portland's surroundings by going to Elk Cove Vineyards (in Gaston), Silverton (The Oregon Garden & The Gordon House) and Carlton (Carlton Winemakers Studio & Soter Vineyards). There's still lots to do: look for gifts at Powell's City of Books, hunt for treasures at Portland Saturday Market, examine the collection at Evergreen Aviation & Space Museum, and learn about winemaking at Willamette Valley Vineyards.

To see ratings, where to stay, more things to do, and tourist information, use the Portland day trip planning site.

Traveling by car from Timberline Lodge to Portland takes 1.5 hours. In July, daytime highs in Portland are 83°F, while nighttime lows are 59°F. You'll have a few hours on the 24th (Wed) to wrap things up before traveling home.

Things to do in Portland

Parks · Wineries · Shopping · Nature

Side Trips

Highlights from your trip
©
Waterfall
Multnomah Falls
4.7

Similar trips

7 days in Oregon BY A USER FROM UNITED STATES October, slow & easy, popular & hidden gems Preferences: October Attraction style: Popular & hidden gems Pace: Slow & easy 12 days in Oregon BY A USER FROM UNITED STATES October, fast-paced, popular sights Preferences: October Attraction style: Popular sights Pace: Fast-paced 16 days in Oregon BY A USER FROM BRAZIL September, popular & hidden gems Preferences: September Attraction style: Popular & hidden gems Pace: Medium 9 days in Oregon BY A USER FROM UNITED STATES October, fast-paced, popular sights Preferences: October Attraction style: Popular sights Pace: Fast-paced 10 days in Oregon BY A USER FROM UNITED STATES October, popular & hidden gems Preferences: October Attraction style: Popular & hidden gems Pace: Medium 5 days in Oregon BY A USER FROM UNITED STATES March, popular sights Preferences: March Attraction style: Popular sights Pace: Medium 13 days in Oregon BY A USER FROM UNITED STATES May, popular sights Preferences: May Attraction style: Popular sights Pace: Medium 7 days in Oregon BY A USER FROM MONGOLIA November, popular sights Preferences: November Attraction style: Popular sights Pace: Medium 10 days in Oregon BY A USER FROM UNITED STATES October, popular sights Preferences: October Attraction style: Popular sights Pace: Medium 6 days in Oregon BY A USER FROM UNITED STATES October, outdoors, beaches, historic sites, wildlife, hidden gems Preferences: October, outdoors, beaches, historic sites, wildlife Attraction style: Hidden gems Pace: Medium 14 days in Oregon BY A USER FROM UNITED STATES October, outdoors, popular & hidden gems Preferences: October, outdoors Attraction style: Popular & hidden gems Pace: Medium 10 days in Oregon BY A USER FROM UNITED STATES December, outdoors, beaches, historic sites, wildlife, fast-paced, popular sights Preferences: December, outdoors, beaches, historic sites, wildlife Attraction style: Popular sights Pace: Fast-paced
See more trips