14 days in Oregon Itinerary

14 days in Oregon Itinerary

Created using Inspirock Oregon trip planner

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Route & dates

14 days in Oregon Itinerary

Start: Newark
Fly + Drive:  10​h 30​min
1
Ashland
— 2 nights
Drive:  4​h 15​min
2
Florence
— 2 nights
Drive:  4​h
3
Cannon Beach
— 3 nights
Drive:  3​h
4
Hood River
— 2 nights
bus:  1​h 15​min
5
Portland
— 4 nights
Fly:  6​h 45​min
End: Newark

2
nights
Ashland

Ashland is a city in Jackson County, in the State of Oregon. Here are some ideas for day two: browse the collection at Jackson County Genealogy Library, walk around Lithia Park, and then let the river carry you with a rafting and tubing tour.

To see traveler tips, other places to visit, ratings, and other tourist information, read Ashland holiday maker .

Newark to Ashland is an approximately 10.5-hour combination of flight and car. You can also drive. Traveling from Newark to Ashland, you'll gain 3 hours due to the time zone difference. While traveling from Newark, expect a bit warmer days and a bit cooler nights in Ashland, ranging from highs of 94°F to lows of 61°F. Finish up your sightseeing early on the 30th (Tue) so you can go by car to Florence.

Things to do in Ashland

Parks Nature Outdoors

Side Trip

Medford
Highlights from your plan
River Rafting & Tubing
Lithia Park ©
Lithia Park
Oregon Shakespeare Festival ©
Oregon Shakespeare Festival

2
nights
Florence

Florence ©
Florence is a coastal city in Lane County, in the U.S. Start off your visit on the 31st (Wed): take a memorable drive along Cape Perpetua Visitor Center - Siuslaw National Forest, take a leisurely stroll along Yachats coastline, then enjoy the sea views from Heceta Head Lighthouse, and finally snap pictures at Siuslaw River Bridge. On the 1st (Thu), you'll have a packed day of sightseeing: Head underground at Sea Lion Caves, then enjoy some diversion at Sand Master Park, and then try for a hole-in-one at Sandland Adventures.

For more things to do, reviews, photos, and other tourist information, you can read our Florence journey planner .

Traveling by car from Ashland to Florence takes 4.5 hours. Alternatively, you can take a bus; or do a combination of bus and flight. While traveling from Ashland, expect colder days and little chillier nights in Florence, ranging from highs of 67°F to lows of 54°F. Finish up your sightseeing early on the 1st (Thu) so you can go by car to Cannon Beach.

Things to do in Florence

Outdoors Parks Nature

Side Trip

Yachats
Highlights from your plan
Yachats coastline ©
Yachats coastline
Sandland Adventures ©
Sandland Adventures

3
nights
Cannon Beach

Cannon Beach ©
Cannon Beach is a city in Clatsop County, Oregon, United States. Explore Cannon Beach's surroundings by going to Astoria (Astoria Column, Astoria-Megler Bridge, & more). There's much more to do: stroll through Haystack Rock, steep yourself in history at Lewis & Clark Salt Works, enjoy the sand and surf at Cannon Beach, and immerse yourself in nature at Ecola State Park.

For photos, maps, traveler tips, and other tourist information, read Cannon Beach trip itinerary planner .

Traveling by car from Florence to Cannon Beach takes 4 hours. Alternatively, you can do a combination of bus and flight; or take a bus. Expect a daytime high around 71°F in August, and nighttime lows around 55°F. Cap off your sightseeing on the 4th (Sun) early enough to go by car to Hood River.

Things to do in Cannon Beach

Parks Nature Outdoors

Side Trips

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

2
nights
Hood River

Hood River ©
The city of Hood River is the seat of Hood River County, Oregon, United States. Kick off your visit on the 5th (Mon): examine the collection at Western Antique Aeroplane & Automobile Museum, then look for all kinds of wild species at Columbia River Gorge National Scenic Area, and then take in the views from Bridge of the Gods. On your second day here, see human ingenuity at work at Bonneville Lock & Dam, examine the collection at Columbia Gorge Discovery Center & Museum, and then stroll through Historic Columbia River Highway State Trail.

To find other places to visit, traveler tips, and other tourist information, read our Hood River attractions planning website .

Traveling by car from Cannon Beach to Hood River takes 3 hours. Alternatively, you can take a bus; or do a combination of bus and train. Traveling from Cannon Beach in August, you will find days in Hood River are somewhat warmer (81°F), and nights are about the same (60°F). Cap off your sightseeing on the 6th (Tue) early enough to catcht the bus to Portland.

Things to do in Hood River

Parks Wildlife Nature

Side Trips

Cascade Locks, Columbia River Gorge National Scenic Area, Historic Columbia River Highway State Trail, Columbia Gorge Discovery Center & Museum
Highlights from your plan
Bonneville Lock & Dam ©
Bonneville Lock & Dam

4
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.
You'll find plenty of places to visit near Portland: Evergreen Aviation & Space Museum (in McMinnville) and Multnomah Falls (in Bridal Veil). Next up on the itinerary: admire the natural beauty at Portland Japanese Garden, walk around South Park Blocks, awaken your taste buds at some of the top wineries in the area, and get to know the resident critters at Oregon Zoo.

For other places to visit, reviews, traveler tips, and other tourist information, refer to the Portland online visit planner .

You can take a bus from Hood River to Portland in 1.5 hours. Alternatively, you can drive; or take a train. In August in Portland, expect temperatures between 85°F during the day and 60°F at night. On the 10th (Sat), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Portland

Parks Tours Outdoors

Side Trips

Evergreen Aviation & Space Museum, Multnomah Falls
Highlights from your plan
Portland Japanese Garden ©
Portland Japanese Garden
International Rose Test Garden ©
International Rose Test Garden
Powell's City of Books ©
Powell's City of Books

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