29 days in Oregon Itinerary

29 days in Oregon Itinerary

Created using Inspirock Oregon planner

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Route & dates

29 days in Oregon Itinerary

Start: North Bend
Drive:  1​h 15​min
1
Florence
— 2 nights
Drive:  1​h 15​min
2
Newport
— 4 nights
Drive:  1​h 45​min
3
Tillamook
— 4 nights
Drive:  1​h 45​min
4
Astoria
— 4 nights
Drive:  2​h
5
Portland
— 6 nights
Bus:  1​h 15​min
6
Hood River
— 5 nights
Drive:  1​h 15​min
7
Timberline Lodge
— 3 nights
Drive:  4​h 45​min
End: North Bend

2
nights
Florence

Florence ©
Florence is a coastal city in Lane County, in the U.S. Get some historical perspective at Heceta Head Lighthouse and Umpqua River Lighthouse. Venture out of the city with trips to Cape Perpetua Visitor Center - Siuslaw National Forest (in Yachats) and Shore Acres State Park (in Coos Bay). There's still lots to do: enjoy some diversion at Sand Master Park, cruise along Oregon Coast, putt your heart out at Sandland Adventures, and kick back and relax at Heceta Beach.

To find reviews, ratings, where to stay, and other tourist information, go to the Florence online road trip planner .

North Bend to Florence is an approximately 1.5-hour bus ride. You can also drive. In May, daytime highs in Florence are 62°F, while nighttime lows are 49°F. Finish your sightseeing early on the 5th (Sun) to allow enough time to drive to Newport.

Things to do in Florence

Parks Outdoors Nature

Side Trips

Oregon Coast, Shore Acres State Park, Cape Perpetua Visitor Center - Siuslaw National Forest, Umpqua River Lighthouse
Highlights from your plan
Heceta Head Lighthouse ©
Heceta Head Lighthouse
Umpqua River Lighthouse ©
Umpqua River Lighthouse

4
nights
Newport

Newport ©
A town that survives on the sea, Newport's population of just over 10,000 supports a healthy commercial fishing industry.
Yaquina Head Lighthouse and Downtown Historic District will appeal to history buffs. Visit Nye Beach and Roads End State Recreation Site for some beach relaxation. Change things up with these side-trips from Newport: Gleneden Beach State Park (in Gleneden Beach), Monteith District (in Albany) and Yachats (Smelt Sands State Park & Yachats coastline). And it doesn't end there: immerse yourself in nature at Devils Punchbowl State Natural Area, take in the views from Yaquina Bay Bridge, meet the residents at Oregon Coast Aquarium, and take a leisurely stroll along Newport's Historic Bayfront.

To find reviews, other places to visit, and tourist information, refer to the Newport trip planner.

Drive from Florence to Newport in 1.5 hours. Alternatively, you can take a bus. Expect a daytime high around 58°F in May, and nighttime lows around 46°F. Finish up your sightseeing early on the 9th (Thu) so you can go by car to Tillamook.

Things to do in Newport

Parks Beaches Outdoors

Side Trips

Albany, Yachats, Gleneden Beach State Park, Roads End State Recreation Site
Highlights from your plan
Yachats coastline ©
Yachats coastline
Nye Beach ©
Nye Beach
Devils Punchbowl State Natural Area ©

4
nights
Tillamook

Tillamook ©
The city of Tillamook is the county seat of Tillamook County, Oregon, United States. Visit Manzanita Beach and Bayocean Peninsula County Park for some beach relaxation. Get some historical perspective at Tillamook Air Museum and Cape Meares Lighthouse. Change things up with these side-trips from Tillamook: Spas & Wellness (in Manzanita), Pacific City (Bob Straub State Park & Cape Kiwanda State Natural Area) and Nehalem Bay State Park (in Nehalem). There's still lots to do: take a memorable drive along Three Capes Scenic Drive, revel in the low prices at The Myrtlewood Factory Outlet, examine the collection at Garibaldi Museum, and enjoy the sand and surf at Rockaway Beach Wayside.

To see maps, other places to visit, and tourist information, use the Tillamook trip planner .

Drive from Newport to Tillamook in 2 hours. Alternatively, you can take a bus. Due to the time zone difference, you'll lose 1 hour traveling from Newport to Tillamook. In May in Tillamook, expect temperatures between 62°F during the day and 46°F at night. Cap off your sightseeing on the 13th (Mon) early enough to go by car to Astoria.

Things to do in Tillamook

Parks Outdoors Beaches

Side Trips

Rockaway Beach, Pacific City, Garibaldi, Three Capes Scenic Drive, Nehalem Bay State Park
Highlights from your plan
Cape Kiwanda State Natural Area ©
Cape Kiwanda State Natural Area
Rockaway Beach Wayside ©
Rockaway Beach Wayside
Tillamook Air Museum ©
Tillamook Air Museum

4
nights
Astoria

Astoria ©
Astoria, named for famed fur trader John Jacob Astor, resides near the mouth of the Columbia River.
You'll get in some beach time at Haystack Rock and Cannon Beach. Get some historical perspective at Fort Clatsop National Memorial and Lightship Columbia. Change things up with these side-trips from Astoria: Cannon Beach (Ecola State Park & Oswald West State Park) and Lewis & Clark Salt Works (in Seaside). The adventure continues: look for all kinds of wild species at Astoria Column, explore the activities along Columbia River Maritime Museum, snap pictures at Astoria-Megler Bridge, and appreciate the history behind Chief Comcomly Memorial.

To see more things to do, where to stay, reviews, and more tourist information, you can read our Astoria online vacation maker .

Traveling by car from Tillamook to Astoria takes 2 hours. Alternatively, you can take a bus. The time zone difference when traveling from Tillamook to Astoria is minus 1 hour. In May, plan for daily highs up to 62°F, and evening lows to 48°F. Finish your sightseeing early on the 17th (Fri) to allow enough time to drive to Portland.

Things to do in Astoria

Parks Nature Historic Sites

Side Trips

Cannon Beach, Lewis & Clark Salt Works
Highlights from your plan
Fort Clatsop National Memorial ©
Fort Clatsop National Memorial
Cannon Beach ©
Cannon Beach
Haystack Rock ©
Haystack Rock

6
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.
Get some historical perspective at Pittock Mansion and Northwest (Nob Hill). Venture out of the city with trips to Mount Angel (Queen of Angels Monastery & St. Mary's Catholic Church), Mount Angel Abbey (in Saint Benedict) and Oregon Garden (in Silverton). Dedicate the 22nd (Wed) to wine at some of the top wineries in the area. Next up on the itinerary: steep yourself in history at Columbia River Highway, admire the natural beauty at Lan Su Chinese Garden, delve into the lush surroundings at The Grotto - National Sanctuary of Our Sorrowful Mother, and do a tasting at Sokol Blosser Winery.

To see other places to visit, more things to do, maps, and other tourist information, you can read our Portland day trip planning website .

Traveling by car from Astoria to Portland takes 2 hours. Alternatively, you can take a bus; or do a combination of bus and train. Traveling from Astoria in May, you will find days in Portland are somewhat warmer (70°F), and nights are about the same (51°F). Cap off your sightseeing on the 23rd (Thu) early enough to go by car to Hood River.

Things to do in Portland

Historic Sites Parks Tours

Side Trips

Mount Angel, Mount Angel Abbey, Oregon Garden, Columbia River Highway, Evergreen Aviation & Space Museum
Highlights from your plan
Portland Japanese Garden ©
Portland Japanese Garden
Columbia River Highway ©
Columbia River Highway
Sokol Blosser Winery ©
Sokol Blosser Winery

5
nights
Hood River

Hood River ©
The city of Hood River is the seat of Hood River County, Oregon, United States. Change things up with these side-trips from Hood River: Multnomah Falls (in Bridal Veil), The Dalles Murals (in The Dalles) and Bonneville Lock & Dam (in Cascade Locks). There's much more to do: explore the activities along Columbia River Gorge National Scenic Area, indulge your thirst for a good beer at Full Sail Brewing Company, stroll through Mount Hood, and hike along Horsetail Falls- Columbia River Gorge.

To see ratings, reviews, other places to visit, and more tourist information, read Hood River route planner .

Getting from Portland to Hood River by car takes about 1.5 hours. Other options: take a bus; or take a train. In May in Hood River, expect temperatures between 67°F during the day and 49°F at night. Wrap up your sightseeing on the 28th (Tue) to allow time to drive to Timberline Lodge.

Things to do in Hood River

Parks Outdoors Nature

Side Trips

Oregon, The Dalles, Cascade Locks, Historic Columbia River Highway State Trail, Multnomah Falls
Highlights from your plan
Mount Hood ©
Mount Hood

3
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.
Start off your visit on the 29th (Wed): take in the awesome beauty at Timberline Lodge and Ski Area, explore the striking landscape of Mt. Hood National Forest, and then take in the dramatic scenery at Little Zigzag Falls. On the 30th (Thu), you'll have a packed day of sightseeing: delve into the lush surroundings at Wildwood Recreation Site, then head outdoors with Henry Creek High Country Guides, and then see the interesting displays at Mt Hood Cultural Center and Museum.

To find other places to visit, reviews, maps, and tourist information, read Timberline Lodge trip planning website .

Traveling by car from Hood River to Timberline Lodge takes 1.5 hours. May in Timberline Lodge sees daily highs of 67°F and lows of 49°F at night. Wrap up your sightseeing by early afternoon on the 31st (Fri) to allow enough time to travel back home.

Things to do in Timberline Lodge

Nature Parks Outdoors

Side Trips

Government Camp, Henry Creek High Country Guides, Mt. Hood National Forest, Wildwood Recreation Site
Highlights from your plan
Timberline Lodge and Ski Area ©
Timberline Lodge and Ski Area
Mt. Hood National Forest ©
Mt. Hood National Forest
Trillium Lake ©
Trillium Lake

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