8 days in Eastern Oregon & Southern Oregon Itinerary

Baker City is a city in and the county seat of Baker County, Oregon, United States. Start off your visit on the 1st (Fri): take an in-depth tour of Baker Heritage Museum, then take an in-depth tour of National Historic Oregon Trail Interpretive Center, and then take an in-depth tour of Leo Adler House Museum.

For maps, more things to do, and other tourist information, read our Baker City trip itinerary maker site.

Boise to Baker City is an approximately 2.5-hour car ride. Traveling from Boise to Baker City, you'll gain 1 hour due to the time zone difference. Traveling from Boise in September, plan for slightly colder nights in Baker City, with lows around 39°F. Cap off your sightseeing on the 1st (Fri) early enough to go by car to John Day.

John Day is a city located about 2mi north of Canyon City in Grant County, Oregon, at the intersection of U.S. Routes 26 and 395. Kick off your visit on the 2nd (Sat): explore the striking landscape of John Day Fossil Beds National Monument. On your second day here, see the interesting displays at Sumpter Valley Railway Depot, then see the interesting displays at Grant County Historical Museum, and then get engrossed in the history at Kam Wah Chung State Heritage Site.

For other places to visit, reviews, ratings, and other tourist information, you can read our John Day trip planning tool.

Traveling by car from Baker City to John Day takes 2 hours. Traveling from Baker City in September, plan for somewhat warmer nights in John Day, with lows around 48°F. Finish your sightseeing early on the 3rd (Sun) so you can drive to Crater Lake National Park.

Reaching a depth of 592 m (1,943 ft), Crater Lake is the deepest lake in the United States.

Start off your visit on the 4th (Mon): explore the striking landscape of Crater Lake National Park. On your second day here, hike along Pinnacles Overlook Hike, admire all the interesting features of Rim Dr, and then stroll through Cleetwood Cove Trail.

For reviews, traveler tips, maps, and more tourist information, use the Crater Lake National Park trip itinerary maker app.

Drive from John Day to Crater Lake National Park in 5.5 hours. When traveling from John Day in September, plan for somewhat warmer days and about the same nights in Crater Lake National Park: temperatures range from 83°F by day to 53°F at night. Cap off your sightseeing on the 5th (Tue) early enough to go by car to Roseburg.

Roseburg is a city in the U.S. state of Oregon. Start off your visit on the 6th (Wed): identify plant and animal life at Wildlife Safari, do a tasting at Girardet Vineyards & Winery, then learn about winemaking at Abacela, and finally try your luck at Seven Feathers Casino Resort.

Klarna Trips's itinerary builder makes planning a Roseburg trip simple and quick.

Traveling by car from Crater Lake National Park to Roseburg takes 2.5 hours. Expect a daytime high around 80°F in September, and nighttime lows around 54°F. Cap off your sightseeing on the 6th (Wed) early enough to go by car to Ashland.

Ashland is a city in Jackson County, in the State of Oregon. On the 7th (Thu), relax and float downstream with a rafting and tubing tour and then catch a live performance at Oregon Shakespeare Festival. On the next day, stop by Rogue Creamery, explore the activities along Rogue River, and then trek along Natural Bridge Loop.

To find maps, traveler tips, where to stay, and tourist information, go to the Ashland trip maker.

Traveling by car from Roseburg to Ashland takes 2 hours. In September, plan for daily highs up to 83°F, and evening lows to 53°F. Finish your sightseeing early on the 8th (Fri) to allow enough time to fly back home.