5 days in Eastern Oregon & Prineville Itinerary

5 days in Eastern Oregon & Prineville Itinerary

Created using Inspirock Oregon trip itinerary planner

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Route & dates

5 days in Eastern Oregon & Prineville Itinerary

Start: Portland
Fly:  3​h
1
Pendleton
— 1 night
Drive:  2​h 15​min
2
Baker City
— 1 night
Drive:  4​h
3
Prineville
— 2 nights
Drive:  3​h 15​min
End: Portland

1
night
Pendleton

Pendleton ©
Pendleton is a city in Umatilla County, Oregon, United States. On the 25th (Sat), get a new perspective on nature at Tamastslikt Cultural Institute, contemplate the long history of Pendleton Woolen Mill Store, and then join in the after-dark buzz at Oregon Grain Growers Brand Distillery. Keep things going the next day: stroll through Helix Wheat Country, head outdoors with Pendleton Round-Up, and then try your luck at Wildhorse Resort and Casino.

To find traveler tips, where to stay, and tourist information, use the Pendleton day trip planning website .

Portland to Pendleton is an approximately 3.5-hour flight. You can also drive. Traveling from Portland in May, you can expect nighttime temperatures to be a bit cooler in Pendleton, with lows of 46°F. Wrap up your sightseeing on the 26th (Sun) to allow time to travel to Baker City.

Things to do in Pendleton

Fun & Games Casinos Outdoors
Highlights from your plan
Wildhorse Resort and Casino ©
Wildhorse Resort and Casino
Pendleton Woolen Mill Store ©
Pendleton Woolen Mill Store
Tamastslikt Cultural Institute ©
Tamastslikt Cultural Institute

1
night
Baker City

Baker City ©
Baker City is a city in and the county seat of Baker County, Oregon, United States. Start off your visit on the 27th (Mon): get engrossed in the history at National Historic Oregon Trail Interpretive Center, explore the landscape on two wheels at Baker City Mini-Loop, and then stroll the grounds of Chinese Cemetery.

To see ratings, where to stay, photos, and tourist information, read our Baker City trip planner.

You can drive from Pendleton to Baker City in 2 hours. Traveling from Pendleton in May, expect Baker City to be a bit cooler, temps between 68°F and 36°F. Cap off your sightseeing on the 27th (Mon) early enough to travel to Prineville.

Things to do in Baker City

Parks Trails Outdoors
Highlights from your plan
Chinese Cemetery ©
Chinese Cemetery

2
nights
Prineville

Prineville ©
Prineville is a city in and the county seat of Crook County, Oregon, United States. Your day-by-day itinerary now includes Painted Hills. On the 28th (Tue), explore the striking landscape at Painted Hills and then admire the majestic nature at Prineville Reservoir State Park.

For more things to do, maps, photos, and other tourist information, you can read our Prineville trip planner .

Getting from Baker City to Prineville by car takes about 4 hours. May in Prineville sees daily highs of 70°F and lows of 37°F at night. On the 29th (Wed), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Prineville

Nature Parks Museums
Highlights from your plan
Painted Hills ©
Painted Hills
Prineville Reservoir State Park ©
Prineville Reservoir State Park
Bowman Museum ©
Bowman Museum