56 days in Oregon Itinerary

56 days in Oregon Itinerary

Created using Inspirock Oregon route planner

Plan created by another user. Make it yours
Fly
1
Portland
— 12 nights
Drive
2
Hood River
— 6 nights
Drive
3
Cannon Beach
— 6 nights
Drive
4
Turner
— 6 nights
Drive
5
Yachats
— 6 nights
Drive
6
Coos Bay
— 6 nights
Drive
7
Crater Lake National Park
— 7 nights
Drive
8
Redmond
— 6 nights
Fly

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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.
Get some historical perspective at Columbia River Highway and Eastbank Esplanade. Step out of the city life by going to Multnomah Falls and Forest Park. You'll find plenty of places to visit near Portland: Carlton (Soter Vineyards & Carlton Winemakers Studio), Jackson Bottom Wetlands Preserve (in Hillsboro) and Sokol Blosser Winery (in Dundee). Next up on the itinerary: admire the natural beauty at Portland Japanese Garden, stroll around Hoyt Arboretum, stop by Powell's City of Books, and sample some tasty brews at a beer tour and tasting.

To see where to stay, ratings, more things to do, and other tourist information, you can read our Portland holiday maker tool.

New York City to Portland is an approximately 9.5-hour flight. You can also drive; or take a train. The time zone difference when traveling from New York City to Portland is minus 3 hours. In April, daily temperatures in Portland can reach 63°F, while at night they dip to 45°F. Wrap up your sightseeing on the 28th (Sat) to allow time to drive to Hood River.

Things to do in Portland

Parks · Nature · Outdoors · Wineries

Side Trips

6
nights
Hood River

The city of Hood River is the seat of Hood River County, Oregon, United States. Visiting Timberline Lodge and Ski Area and Historic Columbia River Highway State Trail will get you outdoors. Venture out of the city with trips to Trillium Lake (in Government Camp), Cascade Locks (Bonneville Lock & Dam & Oneonta Gorge) and Mt. Hood Meadows (in Parkdale). Next up on the itinerary: contemplate the waterfront views at Columbia River Gorge National Scenic Area, stop by Apple Valley Country Store, relax in the rural setting at Lavender Valley, and tour the pleasant surroundings at Mirror Lake Trail.

For reviews, where to stay, photos, and tourist information, read Hood River trip maker.

Traveling by car from Portland to Hood River takes 1.5 hours. Alternatively, you can take a bus; or take a train. When traveling from Portland in April, plan for little chillier days in Hood River, with highs around 58°F, while nights are about the same with lows around 43°F. Wrap up your sightseeing on the 4th (Fri) early enough to drive to Cannon Beach.

Things to do in Hood River

Parks · Outdoors · Nature · Winter Sports

Side Trips

6
nights
Cannon Beach

Cannon Beach is a city in Clatsop County, Oregon, United States. Get outdoors at Haystack Rock and Cannon Beach. Fort Clatsop National Memorial and Cape Meares Lighthouse will appeal to history buffs. You'll find plenty of places to visit near Cannon Beach: Astoria (Astoria Column, Columbia River Maritime Museum, &more) and Tillamook Country Smoker (in Bay City). There's much more to do: immerse yourself in nature at Ecola State Park, take in the awesome beauty at Neahkahnie Mountain, stop by Beach Books, and enjoy the sand and surf at Manzanita Beach.

For reviews, photos, traveler tips, and more tourist information, refer to the Cannon Beach holiday maker app.

You can drive from Hood River to Cannon Beach in 3 hours. Other options are to take a bus; or do a combination of train and bus. When traveling from Hood River in May, plan for little chillier days in Cannon Beach, with highs around 62°F, while nights are about the same with lows around 48°F. Finish your sightseeing early on the 10th (Thu) so you can travel to Turner.

Things to do in Cannon Beach

Parks · Nature · Beaches · Outdoors

Side Trips

6
nights
Turner

Turner is a city in Marion County, Oregon, United States. Deepen your sense of the past at sights like The Oregon Garden and Deepwood Museum & Gardens. Escape the urban bustle at Silver Falls State Park and Peavy Arboretum. Explore the numerous day-trip ideas around Turner: Salem (Cristom Vineyards & Bethel Heights Vineyard), Siuslaw National Forest (in Corvallis) and Evergreen Aviation & Space Museum (in McMinnville). Next up on the itinerary: steep yourself in history at Bush's Pasture Park, get in on the family fun at Enchanted Forest Theme Park, identify plant and animal life at Baskett Slough National Wildlife Refuge, and see where the action happens at Hayward Field.

To see ratings, where to stay, and more tourist information, read our Turner road trip planning site.

Getting from Cannon Beach to Turner by car takes about 2.5 hours. Traveling from Cannon Beach in May, you will find days in Turner are somewhat warmer (71°F), and nights are about the same (48°F). Finish your sightseeing early on the 16th (Wed) so you can drive to Yachats.

Things to do in Turner

Parks · Nature · Historic Sites · Wineries

Side Trips

6
nights
Yachats

Yachats is a small coastal city in Lincoln County, Oregon, United States. Take a break from the city and head to Cape Perpetua Visitor Center - Siuslaw National Forest and Yaquina Head Outstanding Natural Area. Your inner history buff will appreciate Yaquina Head Lighthouse and Heceta Head Lighthouse. You'll find plenty of places to visit near Yachats: Depoe Bay (Ainslee's Salt Water Taffy, Fogarty Creek State Recreation Area, &more), Sandland Adventures (in Florence) and Newport (Nye Beach, Oregon Coast Aquarium, &more). Next up on the itinerary: take in the waterfront at Yachats coastline, immerse yourself in nature at Seal Rock State Wayside, look for gifts at The Chocolate Frog, and Head underground at Sea Lion Caves.

To see other places to visit, photos, more things to do, and other tourist information, use the Yachats trip planner.

You can drive from Turner to Yachats in 2.5 hours. Traveling from Turner in May, expect nights in Yachats to be about the same, around 46°F, while days are slightly colder, around 58°F. Wrap up your sightseeing on the 22nd (Tue) early enough to drive to Coos Bay.

Things to do in Yachats

Parks · Nature · Outdoors · Beaches

Side Trips

6
nights
Coos Bay

Coos Bay is a city located in Coos County, Oregon, United States, where the Coos River enters Coos Bay on the Pacific Ocean. Visiting Face Rock State Scenic Viewpoint and Wildlife Safari will get you outdoors. Coquille River Lighthouse and Cape Blanco Lighthouse will appeal to history buffs. Venture out of the city with trips to Langlois Market (in Langlois), Oregon Dunes National Recreation Area (in Reedsport) and Bandon (West Coast Game Park Safari & Bandon Crossings Golf Course). There's still lots to do: immerse yourself in nature at Shore Acres State Park, tee off at Bandon Dunes Golf Resort, and snap pictures at McCullough Memorial Bridge.

To see maps, traveler tips, and more tourist information, read Coos Bay tour planning website.

You can drive from Yachats to Coos Bay in 2 hours. In May in Coos Bay, expect temperatures between 62°F during the day and 49°F at night. Finish your sightseeing early on the 28th (Mon) to allow enough time to travel to Crater Lake National Park.

Things to do in Coos Bay

Parks · Nature · Wildlife · Golf

Side Trips

7
nights
Crater Lake National Park

Reaching a depth of 592 m (1,943 ft), Crater Lake is the deepest lake in the United States.
Get in touch with nature at Crater Lake National Park and Upper and Lower Table Rock. Explore Crater Lake National Park's surroundings by going to Grants Pass (Wooldridge Creek Winery, Bear Hotel Artworks Museum, &more), Ashland (Lithia Park & Oregon Shakespeare Festival) and Rogue River (in Medford). There's lots more to do: admire the majestic nature at Joseph H. Stewart State Recreation Area, admire the sheer force of Salt Creek Falls, and steep yourself in history at Rim Village Visitor Center.

To find photos, maps, reviews, and other tourist information, read Crater Lake National Park online day trip planner.

You can drive from Coos Bay to Crater Lake National Park in 4 hours. Expect a bit warmer weather when traveling from Coos Bay in May: highs in Crater Lake National Park hover around 77°F, while lows dip to 49°F. Wrap up your sightseeing by early afternoon on the 4th (Mon) to allow time for travel to Redmond.

Things to do in Crater Lake National Park

Parks · Nature · Nightlife · Historic Sites

Side Trips

6
nights
Redmond

Redmond is a city in Deschutes County, Oregon, United States. Escape the urban bustle at Smith Rock State Park and Tumalo Falls. Explore the numerous day-trip ideas around Redmond: Sisters (Sahalie and Koosah Falls & McKenzie Pass-Santiam Pass loop) and Bend (High Desert Museum & Hosmer Lake). There's lots more to do: take a peaceful walk through Deschutes National Forest, immerse yourself in nature at Peter Skene Ogden State Park, contemplate the waterfront views at Deschutes River, and tee off at Eagle Crest Resort Golf Courses.

To see other places to visit, traveler tips, ratings, and other tourist information, read Redmond road trip planning tool.

You can drive from Crater Lake National Park to Redmond in 3 hours. Traveling from Crater Lake National Park in June, things will get a bit cooler in Redmond: highs are around 79°F and lows about 43°F. On the 10th (Sun), you're off to home.

Things to do in Redmond

Parks · Nature · Outdoors · Museums

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.