18 days in Oregon Itinerary

18 days in Oregon Itinerary

Created using Inspirock Oregon travel planner

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Route & dates

18 days in Oregon Itinerary

Start: Chicago
Fly:  9​h
1
Bend
— 3 nights
Drive:  3​h
2
Prospect
— 2 nights
Drive:  3​h
3
Coos Bay
— 1 night
Drive:  2​h 30​min
4
Newport
— 3 nights
Drive:  3​h
5
Cannon Beach
— 2 nights
Drive:  3​h
6
Hood River
— 3 nights
Drive:  1​h 30​min
7
Maupin
— 2 nights
Drive + Fly:  9​h
End: Chicago

3
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.
Your day-by-day itinerary now includes Seventh Mountain River Company as well as Bend Escape Room. Discover out-of-the-way places like Sparks Lake and Mt. Bachelor Ski Area. When in Bend, make a side trip to see Lava Cast Forest Trail in La Pine, approximately 36 minutes away. There's much more to do: Head underground at Lava River Cave, admire the sheer force of Tumalo Falls, explore and take pictures at Pilot Butte State Scenic Viewpoint, and take in the dramatic natural features at Newberry National Volcanic Monument.

To see reviews, where to stay, ratings, and more tourist information, read our Bend travel website .

Chicago to Bend is an approximately 9-hour flight. You can also do a combination of subway, bus, and flight; or drive. The time zone difference moving from Central Standard Time to Pacific Standard Time is minus 2 hours. Traveling from Chicago in June, things will get slightly colder in Bend: highs are around 75°F and lows about 45°F. Wrap up your sightseeing on the 8th (Sat) to allow time to travel to Prospect.

Things to do in Bend

Parks Outdoors Nature

Side Trip

Lava Cast Forest Trail
Highlights from your plan
Newberry National Volcanic Monument ©
Seventh Mountain River Company ©
Seventh Mountain River Company
Lava River Cave ©
Lava River Cave

2
nights
Prospect

Prospect ©
Prospect is an unincorporated community in Jackson County, in the U.S. Kick off your visit on the 9th (Sun): trek along Cleetwood Cove Trail, then admire all the interesting features of Rim Dr, then tour the pleasant surroundings at Pinnacles Trail, and finally look for all kinds of wild species at Rogue River Gorge Viewpoint. Keep things going the next day: explore the wealth of natural beauty at Crater Lake National Park.

For ratings, more things to do, traveler tips, and more tourist information, you can read our Prospect trip itinerary maker tool .

Drive from Bend to Prospect in 2.5 hours. In June, Prospect is a bit warmer than Bend - with highs of 86°F and lows of 55°F. Finish your sightseeing early on the 10th (Mon) to allow enough time to travel to Coos Bay.

Things to do in Prospect

Parks Nature Outdoors

Side Trip

Crater Lake National Park
Highlights from your plan
Crater Lake National Park ©
Crater Lake National Park
Rim Dr ©
Rim Dr
Cleetwood Cove Trail ©
Cleetwood Cove Trail

1
night
Coos Bay

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. Start off your visit on the 11th (Tue): steep yourself in history at Marshfield Pioneer Cemetery, immerse yourself in nature at Shore Acres State Park, and then immerse yourself in nature at Cape Arago State Park.

To see where to stay, other places to visit, maps, and other tourist information, you can read our Coos Bay trip maker app .

You can drive from Prospect to Coos Bay in 3.5 hours. While traveling from Prospect, expect much colder days and about the same nights in Coos Bay, ranging from highs of 65°F to lows of 52°F. Wrap up your sightseeing on the 11th (Tue) early enough to travel to Newport.

Things to do in Coos Bay

Nature Parks Historic Sites
Highlights from your plan
Shore Acres State Park ©
Shore Acres State Park
Cape Arago State Park ©
Cape Arago State Park
Marshfield Pioneer Cemetery ©
Marshfield Pioneer Cemetery

3
nights
Newport

Newport ©
A town that survives on the sea, Newport's population of just over 10,000 supports a healthy commercial fishing industry.
You've now added Whale Research EcoExcursions to your itinerary. Bring the kids along to Sand Master Park and Nye Beach. Explore hidden gems such as Devil's Churn and Thor's Well. Get out of town with these interesting Newport side-trips: Florence (Jessie M. Honeyman Memorial State Park, Sandland Adventures, & more). There's more to do: engage your brain at Hatfield Marine Science Center.

To find photos, where to stay, other places to visit, and more tourist information, use the Newport travel itinerary planner .

You can drive from Coos Bay to Newport in 2.5 hours. In June in Newport, expect temperatures between 61°F during the day and 48°F at night. Cap off your sightseeing on the 14th (Fri) early enough to go by car to Cannon Beach.

Things to do in Newport

Parks Outdoors Nature

Side Trips

Florence, Yachats, Whale Research EcoExcursions
Highlights from your plan
Nye Beach ©
Nye Beach
Sand Master Park - Sandboarding ©
Sand Master Park - Sandboarding
Hatfield Marine Science Center ©
Hatfield Marine Science Center

2
nights
Cannon Beach

Cannon Beach ©
Cannon Beach is a city in Clatsop County, Oregon, United States. On the 15th (Sat), take in the dramatic natural features at Haystack Rock, then immerse yourself in nature at Hug Point State Park, then get engrossed in the history at Cannon Beach History Center and Museum, and finally sample the fine beverages at Cannon Beach Distillery. Get ready for a full day of sightseeing on the next day: admire the majestic nature at Oswald West State Park, admire the majestic nature at Ecola State Park, and then visit a coastal fixture at Tillamook Rock Light.

For where to stay, reviews, other places to visit, and more tourist information, use the Cannon Beach day trip planning website .

You can drive from Newport to Cannon Beach in 3 hours. Another option is to take a bus. Expect a daytime high around 66°F in June, and nighttime lows around 52°F. Wrap up your sightseeing on the 16th (Sun) early enough to drive to Hood River.

Things to do in Cannon Beach

Nature Parks Outdoors
Highlights from your plan
Haystack Rock ©
Haystack Rock
Hug Point State Park ©
Hug Point State Park
Ecola State Park ©
Ecola State Park

3
nights
Hood River

Hood River ©
The city of Hood River is the seat of Hood River County, Oregon, United States. On the 17th (Mon), take in the dramatic scenery at Multnomah Falls and then contemplate the geological forces at Mount Hood. On your second day here, contemplate the waterfront views at Trillium Lake.

To see reviews, more things to do, where to stay, and other tourist information, read Hood River travel planner .

You can drive from Cannon Beach to Hood River in 3 hours. Alternatively, you can take a bus; or do a combination of bus and train. Traveling from Cannon Beach in June, you will find days in Hood River are somewhat warmer (72°F), and nights are about the same (55°F). Wrap up your sightseeing by early afternoon on the 19th (Wed) to allow enough time to drive to Maupin.

Things to do in Hood River

Parks Nature Outdoors

Side Trips

Trillium Lake, Multnomah Falls, Bonneville Hatchery
Highlights from your plan
Mount Hood ©
Mount Hood
Multnomah Falls ©
Multnomah Falls
Trillium Lake ©
Trillium Lake

2
nights
Maupin

Maupin ©
Maupin is a city in Wasco County, Oregon, United States. You've now added River Drifters to your itinerary. Kick off your visit on the 19th (Wed): relax and float downstream with River Drifters. On the 20th (Thu), you'll have a packed day of sightseeing: examine the collection at Sherman County Historical Museum and then look for all kinds of wild species at Cottonwood Canyon State Park.

For where to stay, ratings, photos, and other tourist information, refer to the Maupin visit planner.

Traveling by car from Hood River to Maupin takes 1.5 hours. Traveling from Hood River in June, expect nights in Maupin to be about the same, around 58°F, while days are a bit warmer, around 82°F. Finish up your sightseeing early on the 21st (Fri) so you can travel back home.

Things to do in Maupin

Outdoors Nature Parks

Side Trips

Sherman County Historical Museum, Cottonwood Canyon State Park
Highlights from your plan
Cottonwood Canyon State Park ©
Cottonwood Canyon State Park
Imperial River Company ©
Imperial River Company
River Drifters ©
River Drifters

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