What are the best hikes in Oregon?

Standouts include Proxy Falls, Watchman Peak (Crater Lake), Trillium Lake Loop (Mt Hood), Tamanawas Falls — 10 trails in all, mapped with difficulty, distance, and elevation on Roamward.

When is the best time to hike in Oregon?

Year-round (Gorge) · summer (volcanoes). Expect drizzle and bring layers.

Are there easy or family-friendly hikes in Oregon?

Yes — gentler options include Proxy Falls, Watchman Peak (Crater Lake), Trillium Lake Loop (Mt Hood), good for kids and the RV/camping crew.

Roamward

Hikes · Oregon

Best hikes in Oregon.

Oregon runs waterfalls in the Columbia Gorge, volcanoes in the Cascades, and a wild, fully public coast — mossy and green west of the mountains, high desert east. The Gorge hikes go nearly year-round; the volcano summits are a short summer window. Expect drizzle and bring layers.

Curated trails10

Distance range1.5–11 mi

Biggest climb4,900 ft

Difficulty4 easy · 3 moderate · 2 hard · 1 expert

TerrainWaterfalls, volcanoes & coast

Best seasonYear-round (Gorge) · summer (volcanoes)

Don’t missMultnomah–Wahkeena Loop

Boots on

10 hikes worth the detour.

Sorted easy to expert. Every one mapped with distance, route type, and elevation gain — built for everyone from the RV & camping crew to the bucket-list crowd.

Proxy Falls

Easy · 1.5 mi · Loop · 200 ft

a moss-draped waterfall off McKenzie Pass

Watchman Peak (Crater Lake)

Easy · 1.6 mi · Out & back · 400 ft

a quick lookout over the caldera

Trillium Lake Loop (Mt Hood)

Easy · 2 mi · Loop · 100 ft

Mt Hood mirrored in the lake — family/RV

Tamanawas Falls

Easy · 3.6 mi · Out & back · 600 ft

a wide waterfall you can walk behind

Tom McCall Point

Moderate · 3.4 mi · Out & back · 1,100 ft

spring wildflowers high over the Columbia

Angel’s Rest (Columbia Gorge)

Moderate · 4.8 mi · Out & back · 1,500 ft

a cliff perch over the river

Multnomah–Wahkeena Loop

Moderate · 5 mi · Loop · 1,600 ft

waterfall after waterfall in the Columbia Gorge

Misery Ridge (Smith Rock)

Hard · 3.7 mi · Loop · 1,000 ft

the iconic loop past Monkey Face

No Name Lake (Broken Top)

Hard · 9 mi · Out & back · 1,500 ft

a turquoise tarn below Broken Top

South Sister Summit

Expert · 11 mi · Out & back · 4,900 ft

a non-technical Cascade volcano summit

Plan the Oregon trip

Hikes, gems, scenic drives — all in one Oregon guide.

See everything worth the detour in Oregon, then let Roamward build the trip around it. Know a Oregon trail we’re missing? Add it — we’re building this with the people who actually hike it.

Full Oregon guide →All states