14 days in Oregon Itinerary

14 days in Oregon Itinerary

Created using Inspirock Oregon itinerary planner

Make it your trip
Fly
1
Hood River
— 2 nights
Drive
2
Portland
— 4 nights
Drive
3
Cannon Beach
— 2 nights
Drive
4
Newport
— 2 nights
Drive
5
Ashland
— 1 night
Drive
6
Crater Lake National Park
— 2 nights
Fly

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Hood River

— 2 nights
The city of Hood River is the seat of Hood River County, Oregon, United States. Take a break from Hood River with a short trip to Bonneville Lock & Dam in Cascade Locks, about 32 minutes away. There's lots more to do: explore the activities along Columbia River Gorge National Scenic Area, tour the pleasant surroundings at Historic Columbia River Highway State Trail, cruise along Hood River County Fruit Loop, and see the interesting displays at Western Antique Aeroplane & Automobile Museum.

To see where to stay, other places to visit, and more tourist information, read Hood River itinerary maker tool.

New York City to Hood River is an approximately 8-hour flight. You can also drive; or do a combination of bus and train. You'll gain 3 hours traveling from New York City to Hood River due to the time zone difference. Plan for slightly colder temperatures traveling from New York City in June, with highs in Hood River at 72°F and lows at 55°F. Finish your sightseeing early on the 18th (Fri) to allow enough time to drive to Portland.

Things to do in Hood River

Parks · Wildlife · Museums · Outdoors

Side Trips

Find places to stay Jun 16 — 18:

Portland

— 4 nights

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.
Change things up with these side-trips from Portland: Natalies Estate Winery (in Newberg), Multnomah Falls (in Bridal Veil) and Evergreen Aviation & Space Museum (in McMinnville). And it doesn't end there: take in nature's colorful creations at International Rose Test Garden, look for gifts at Powell's City of Books, get to know the resident critters at Oregon Zoo, and stroll through Wildwood Trail.

For ratings, reviews, traveler tips, and other tourist information, you can read our Portland trip itinerary builder.

Drive from Hood River to Portland in 1.5 hours. Alternatively, you can take a bus; or take a train. In June in Portland, expect temperatures between 77°F during the day and 56°F at night. Wrap up your sightseeing on the 22nd (Tue) early enough to drive to Cannon Beach.

Things to do in Portland

Parks · Museums · Trails · Outdoors

Side Trips

Find places to stay Jun 18 — 22:

Cannon Beach

— 2 nights
Cannon Beach is a city in Clatsop County, Oregon, United States. Kick off your visit on the 23rd (Wed): immerse yourself in nature at Ecola State Park, get engrossed in the history at Cannon Beach History Center and Museum, then explore the striking landscape at Haystack Rock, and finally enjoy the sand and surf at Cannon Beach. Here are some ideas for day two: immerse yourself in nature at Hug Point State Park, admire the majestic nature at Oswald West State Park, then look for gifts at Cloud and Leaf Bookstore, and finally admire the majestic nature at Nehalem Bay State Park.

To find reviews, photos, ratings, and other tourist information, refer to the Cannon Beach trip itinerary planner.

Getting from Portland to Cannon Beach by car takes about 1.5 hours. Other options: take a bus. When traveling from Portland in June, plan for a bit cooler days in Cannon Beach, with highs around 66°F, while nights are about the same with lows around 52°F. Finish your sightseeing early on the 24th (Thu) so you can drive to Newport.

Things to do in Cannon Beach

Parks · Nature · Outdoors · Beaches

Side Trips

Find places to stay Jun 22 — 24:

Newport

— 2 nights
A town that survives on the sea, Newport's population of just over 10,000 supports a healthy commercial fishing industry.
On the 25th (Fri), tour the pleasant surroundings at Cape Perpetua Visitor Center - Siuslaw National Forest, then take a leisurely stroll along Yachats coastline, and then enjoy the sea views from Heceta Head Lighthouse. Get ready for a full day of sightseeing on the next day: observe the fascinating underwater world at Oregon Coast Aquarium, visit a coastal fixture at Yaquina Head Lighthouse, and then identify plant and animal life at Yaquina Head Outstanding Natural Area.

For where to stay, more things to do, and tourist information, you can read our Newport trip maker site.

Traveling by car from Cannon Beach to Newport takes 3 hours. Alternatively, you can take a bus. While traveling from Cannon Beach, expect a bit cooler days and about the same nights in Newport, ranging from highs of 61°F to lows of 48°F. Finish your sightseeing early on the 26th (Sat) so you can drive to Ashland.

Things to do in Newport

Parks · Historic Sites · Zoos & Aquariums · Wildlife

Side Trips

Find places to stay Jun 24 — 26:

Ashland

— 1 night
Ashland is a city in Jackson County, in the State of Oregon. Kick off your visit on the 27th (Sun): stroll around Lithia Park, catch a live performance at Oregon Shakespeare Festival, and then relax and float downstream with a rafting and tubing tour.

To find reviews, traveler tips, other places to visit, and more tourist information, read our Ashland trip planner.

You can drive from Newport to Ashland in 5 hours. Other options are to do a combination of bus and flight; or take a bus. Traveling from Newport in June, expect nights in Ashland to be somewhat warmer, around 55°F, while days are much warmer, around 86°F. Finish your sightseeing early on the 27th (Sun) so you can drive to Crater Lake National Park.

Things to do in Ashland

Parks · Tours · Outdoors · Adventure
Find places to stay Jun 26 — 27:

Crater Lake National Park

— 2 nights
Reaching a depth of 592 m (1,943 ft), Crater Lake is the deepest lake in the United States.
On the 28th (Mon), explore the wealth of natural beauty at Crater Lake National Park.

To see more things to do, photos, ratings, and tourist information, you can read our Crater Lake National Park day trip planner.

Drive from Ashland to Crater Lake National Park in 2 hours. Alternatively, you can do a combination of bus and taxi. In June, daily temperatures in Crater Lake National Park can reach 86°F, while at night they dip to 55°F. Wrap up your sightseeing on the 29th (Tue) to allow time to fly back home.

Things to do in Crater Lake National Park

Parks · Nature
Find places to stay Jun 27 — 29:
Highlights from your trip

Oregon travel guide

4.5
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.