19 days in Oregon Itinerary

19 days in Oregon Itinerary

Created using Inspirock Oregon route maker

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Route & dates

19 days in Oregon Itinerary

Start: New York City
+3
bus + Fly + tram + bus:  12​h
1
Cannon Beach
— 5 nights
Drive:  1​h 45​min
2
McMinnville
— 4 nights
Drive:  2​h
3
Timberline Lodge
— 4 nights
Drive:  2​h 30​min
4
Bend
— 4 nights
Fly + bus:  11​h 30​min
End: New York City

5
nights
Cannon Beach

Cannon Beach ©
Cannon Beach is a city in Clatsop County, Oregon, United States. Deepen your sense of the past at sights like Fort Clatsop National Memorial and Cape Meares Lighthouse. We've included these beaches for you: Haystack Rock and Manzanita Beach. Venture out of the city with trips to Tillamook Air Museum (in Tillamook) and Astoria (Astoria Column & Columbia River Maritime Museum). There's lots more to do: kick back and relax at Cannon Beach, immerse yourself in nature at Ecola State Park, look for gifts at Beach Books, and savor the flavors at Seaside Candyman.

Planning Cannon Beach trip won't be overwheling when you use's Insprock itinerary maker.

New York City to Cannon Beach is an approximately 12-hour combination of bus and flight. You can also do a combination of train, flight, and bus; or drive. The time zone difference moving from Eastern Standard Time to Pacific Standard Time is minus 3 hours. Traveling from New York City in June, expect Cannon Beach to be slightly colder, temps between 65°F and 52°F. Wrap up your sightseeing on the 15th (Fri) to allow time to travel to McMinnville.

Things to do in Cannon Beach

Parks Nature Historic Sites

Side Trips

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

4
nights
McMinnville

McMinnville ©
McMinnville is the county seat and largest city of Yamhill County, Oregon, United States. Popular historic sites such as Pittock Mansion and Oregon Garden are in your itinerary. Get some cultural insight at Evergreen Aviation & Space Museum and Portland Art Museum. Explore the numerous day-trip ideas around McMinnville: Portland (Portland Japanese Garden, Oaks Bottom Wildlife Refuge, & more) and Willamette Valley Vineyards (in Turner). The adventure continues: admire the verdant scenery at Sokol Blosser Winery and do a tasting at Carlton Winemakers Studio.

For reviews, ratings, photos, and more tourist information, read McMinnville holiday planner.

Traveling by car from Cannon Beach to McMinnville takes 2 hours. When traveling from Cannon Beach in June, plan for a bit warmer days in McMinnville, with highs around 74°F, while nights are about the same with lows around 49°F. Cap off your sightseeing on the 19th (Tue) early enough to travel to Timberline Lodge.

Things to do in McMinnville

Parks Wineries Museums

Side Trips

Portland, Willamette Valley Vineyards, Carlton Winemakers Studio, Oregon Garden, Sokol Blosser Winery
Highlights from your plan
Evergreen Aviation & Space Museum ©
Evergreen Aviation & Space Museum
Sokol Blosser Winery ©
Sokol Blosser Winery
Willamette Valley Vineyards ©
Willamette Valley Vineyards

4
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.
Take a break from the city and head to Columbia River Gorge National Scenic Area and Multnomah Falls. Satisfy your inner culture vulture at Timberline Lodge and Ski Area and Western Antique Aeroplane & Automobile Museum. You'll find plenty of places to visit near Timberline Lodge: Columbia Gorge Discovery Center & Museum (in The Dalles) and Historic Columbia River Highway State Trail (in Mosier).

For ratings, reviews, other places to visit, and more tourist information, go to the Timberline Lodge trip itinerary tool .

Drive from McMinnville to Timberline Lodge in 2.5 hours. Wrap up your sightseeing on the 23rd (Sat) early enough to travel to Bend.

Things to do in Timberline Lodge

Nature Parks Outdoors

Side Trips

Hood River, Columbia Gorge Discovery Center & Museum, Historic Columbia River Highway State Trail, Multnomah Falls, Wildwood Recreation Site
Highlights from your plan
Timberline Lodge and Ski Area ©
Timberline Lodge and Ski Area
Multnomah Falls ©
Multnomah Falls

4
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 High Desert Museum and Smith Rock State Park. Venture out of the city with trips to Sisters (McKenzie Pass-Santiam Pass loop & Sahalie and Koosah Falls) and Peter Skene Ogden State Park (in Terrebonne). Next up on the itinerary: delve into the lush surroundings at Deschutes National Forest, Head underground at Lava River Cave, tour the pleasant surroundings at Drake Park, and contemplate the waterfront views at Deschutes River.

For photos, reviews, traveler tips, and tourist information, read Bend trip itinerary maker site .

Traveling by car from Timberline Lodge to Bend takes 2.5 hours. June in Bend sees daily highs of 72°F and lows of 44°F at night. Finish up your sightseeing early on the 27th (Wed) so you can travel back home.

Things to do in Bend

Parks Nature Wildlife

Side Trips

Sisters, Smith Rock State Park, Peter Skene Ogden State Park
Highlights from your plan
High Desert Museum ©
High Desert Museum
Smith Rock State Park ©
Smith Rock State Park
Deschutes National  Forest ©
Deschutes National Forest

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