A 3-day self-drive loop from Portland along the Historic Columbia River Highway’s waterfalls, up through Hood River’s fruit orchards to a concrete replica of Stonehenge above the river, and a last night at the historic Timberline Lodge on Mount Hood — with real inns, real restaurants, and 2026 prices for every stop.
Day 1Portland to Hood River on the Historic Highway
Pick up a rental car in Portland and follow the 1916 Historic Columbia River Highway east, stopping at its waterfalls and viewpoints on the way to an overnight in Hood River.
🚗 Rental Car Pickup: Enterprise Rent-A-Car, PDX
from $45 USD / day
Pick up a car at Portland International Airport before heading east on I-84 and then the old Historic Columbia River Highway, which parallels the interstate through the western gorge.
Enterprise Rent-A-Car — PDX · enterprise.com
📸 Vista House at Crown Point
~30 minutes · free (donations welcome)
An octagonal 1918 rotunda perched 733 feet above the river, built as a rest stop for early highway travelers and still the gorge’s signature photo overlook, with exhibits inside on the highway’s construction.
Vista House · vistahouse.com
💧 Multnomah Falls
~1 hour · free (timed parking permit required late May–early Sept)
Oregon’s tallest waterfall drops 620 feet in two tiers beneath the arched Benson Bridge — the short paved trail to the bridge gets crowded by midmorning, so arrive early or check recreation.gov for the seasonal parking permit.
🛎️ Check-In: Hood River Hotel
From $175 USD / night, for 2 people
A restored 1913 brick hotel in downtown Hood River with a wood-fired sauna and a lobby bar, an easy walk to the town’s riverfront brewpubs and windsurf-shop storefronts.
Hood River Hotel · (541) 386-1900 · hoodriverhotel.com
🍺 Dinner: pFriem Family Brewers
~1.5 hours · dinner ~$20–$30 USD / person
A riverfront brewery and restaurant on the Hood River waterfront, pouring Belgian-inspired ales beside a wood-fired kitchen menu and a patio that looks out over the windsurfing launch.
pFriem Family Brewers · (541) 321-0490 · pfriembeer.com
Day 2The Fruit Loop, Maryhill’s Stonehenge & Mount Hood
A morning through Hood River Valley’s orchard stands, an afternoon crossing into Washington for a concrete Stonehenge replica above the river, then a climb up to Mount Hood for the night.
🌲 Hood River Fruit Loop: Draper Girls Country Farm
~1.5 hours · free to browse, produce & cider donuts ~$5–$15
One stop on the 35-mile Hood River Fruit Loop through orchards below Mount Hood — a family farm stand selling fresh apples, pears and cider donuts, with a petting-zoo barn and pick-your-own pumpkins in fall.
Draper Girls Country Farm · drapergirlscountryfarm.com
🏛️ Maryhill Museum of Art & Stonehenge Memorial
~2 hours · museum $23 USD / adult, Stonehenge Memorial free
A clifftop mansion-turned-museum of Rodin sculptures and Native American artifacts overlooking the Columbia, three miles from a full-scale concrete replica of Stonehenge that Sam Hill built as a World War I memorial.
Maryhill Museum of Art · maryhillmuseum.org
📸 Rowena Crest Viewpoint
~30 minutes · free
A hairpin overlook on the old highway above the Tom McCall Preserve, where the gorge’s green, waterfall-fed west gives way to the dry grasslands of the east — wildflowers cover the plateau below in April and May.
🛎️ Check-In: Timberline Lodge
From $290 USD / night, for 2 people
A WPA-built 1937 stone-and-timber lodge on Mount Hood’s south flank, its lobby anchored by a hand-forged iron chandelier and a hexagonal fireplace — recognizable as the exterior of the Overlook Hotel in “The Shining.”
Timberline Lodge · (503) 272-3410 · timberlinelodge.com
Day 3Mount Hood & the Drive Back to Portland
A morning around Timberline Lodge and a quiet alpine lake before the scenic drive back down to Portland.
🥾 Timberline Lodge Grounds & Silcox Hut Trail
~1 hour · free
Walk the lodge’s hand-hewn timber halls (self-guided, or ask at the front desk about a docent tour) before a short stretch of the Timberline Trail toward Silcox Hut for a close-up view of the mountain’s summit snowfields.
📸 Trillium Lake
~30 minutes · free (day-use parking fee at the boat ramp)
A small reservoir a few minutes off Highway 26 with one of the most photographed views of Mount Hood in Oregon, its snowy summit mirrored in the water on a still morning.
🚗 Self-Drive: Mount Hood to Portland (PDX)
~1.5 hours, 60 miles via US-26 W
Return the rental car at Portland International Airport, or continue into downtown Portland — build in extra time on Sunday afternoons when ski traffic backs up on Highway 26.
Download your itinerary here
