A 3-Day Eastern Oregon Weekend Itinerary

Dust rising from a truck traveling in Eastern Oregon with the Cascades in the background. Photo credit by: Theo Bickel.

Eastern Oregon is a whole different vibe. Fewer crowds, bigger skies, and landscapes that shift from high desert to painted hills in a single drive. If you're looking for a place to slow down, disconnect from the usual, and soak in some jaw-dropping views, this Eastern Oregon weekend itinerary will show you how to make the most of three days out east.

Day 1: Into the Desert – Drive, Fossils, and Painted Hills

Morning:Start early from Bend or Portland and make your way toward the John Day Fossil Beds. Pack snacks and fuel up—Eastern Oregon towns are few and far between, and cell service gets spotty.

Midday:Stop at the Thomas Condon Paleontology Center to get context on the fossil-rich terrain you're about to explore. Then head straight to the Painted Hills Unit—one of Oregon’s most surreal natural wonders. The short Painted Cove Trail is a must, and the overlook gives you that layered rainbow view you’ve probably seen on postcards.

Afternoon:Continue the scenic loop toward Mitchell, a tiny but charming town with a couple of cool shops and a laid-back vibe. Grab a late lunch or snack at Tiger Town Brewing Co. and explore the few blocks downtown.

Evening:Check into a rustic cabin, boutique inn, or campsite in or around Mitchell. Watch the sunset at Sheep Rock or stargaze from your porch—this is some of Oregon’s darkest sky territory.

Day 2: Hike, Soak, and Explore the Wild Side

Morning:Drive southeast toward Sumpter or Prairie City. If you're a history buff, the Sumpter Valley Dredge offers a fascinating peek into Oregon’s gold rush past. For hikers, head to Strawberry Mountain Wilderness and tackle the Strawberry Lake Trail—a relatively moderate 5-mile round trip that offers alpine lake views.

Midday:Make your way to Canyon City or John Day for lunch. Try 1188 Brewing Company or Outpost Pizza, and stop by the Grant County Historical Museum for a look at old-school Oregon life.

Afternoon:Drive south toward Crystal Crane Hot Springs outside Burns. These natural mineral springs are the perfect way to unwind after a day of dusty trails and mountain air.

Evening:Stay the night at the hot springs (they offer cabins, tent sites, and soaking tubs) or continue into Burns to stay in town. Expect peace, quiet, and maybe a jackrabbit or two under the stars.

Day 3: High Desert and Volcanic Views

Morning:Make the drive south to the Malheur National Wildlife Refuge. Even if you're not a birder, the high-desert marshland here is serene and striking. If you're traveling in spring or fall, expect to see sandhill cranes, hawks, and dozens of migratory birds.

Midday:Take the long, beautiful drive to Steens Mountain. Even if you don’t have time for the full loop (often closed due to snow until mid-summer), the approach is worth it. If you're lucky with timing, take in the view from Kiger Gorge Overlook or Wildhorse Lake Trailhead.

Afternoon:Make your way back toward Bend or Boise depending on your route. Stop at Frenchglen Mercantile for a drink or snack and appreciate the sense of remoteness before returning to the grid.

Eastern Oregon rewards the curious and the patient. You won’t find fast wifi or chain stores out here—but you will find quiet trails, wide views, and the kind of solitude that sticks with you long after the trip ends.

Want a custom Eastern Oregon weekend itinerary designed around your pace, interest, or camping style? I can put one together just for you.Planning to visit in a different season or add a detour to the Wallowas? Drop a comment and I’ll build that into a future field report.