When hikers ask which trails in Oregon are worth a full day — or several — the conversation always circles back to the same handful of routes. Below we've ranked the ten longest hiking trails in Oregon by total mapped distance, drawing from the 14,971 trails OutsideAtlas currently tracks in the state. Each entry includes the distance, what makes the route distinctive, and an honest note on who should actually attempt it.
Oregon ranges from the rugged Pacific coast through the Coast Range, the agricultural Willamette Valley, the Cascades (Mount Hood, the Three Sisters), and the high desert east of the divide. The PCT, the Oregon Coast Trail (382 miles), and the Timberline Trail combine for hundreds of miles of formal long-distance mileage. July-September for high Cascades; coast year-round; high desert spring and fall.
Our rankings here are data-driven — pulled from the 14,971 mapped entries OutsideAtlas tracks in Oregon — but the data has limits worth being honest about. OpenStreetMap distance tags are crowd-sourced and inconsistent. A route may appear longer or shorter than the official measurement, especially when long-distance trails (like state and national scenic trails) are tagged in segments rather than as a single relation.
The Ranking
Ranked from #1 to #10. Click through any entry for the full trail page — map, elevation profile, weather forecast, and direct OpenStreetMap source link.
#1. Hollister Trail
At 1.50 mi, Hollister Trail tops the list — a route built for hikers who plan in days, not hours. Expect 1.50 mi, gravel surface on a forgiving grade. Local trail-association reports tend to agree this is one of the better-maintained options in the area, which matters more on a hike of this length than on a quick walk. A gravel-and-dirt tread holds up well after rain, though loose surface on descents calls for trekking poles or careful footing. Plan as a multi-day if you're not used to single-push 20+ mile days; resupply or shuttle logistics matter here. See full trail details, map, and current weather on OutsideAtlas for the most current information.
Open the Hollister Trail trail page →Map, elevation profile, current weather, and OSM source.#2. Umatilla River Parkway
Umatilla River Parkway earns the #2 spot for its sheer distance, though the exact mileage in OpenStreetMap data is a rough estimate. Expect 1,096 ft of gain, concrete:plates surface on a forgiving grade. The route is well documented in OpenStreetMap, which is what put it on our radar — community-mapped routes tend to be the ones that get hiked enough to stay open. A paved surface makes this one of the more accessible options on the list — good for strollers, mobility aids, and wet-weather days. Plan as a multi-day if you're not used to single-push 20+ mile days; resupply or shuttle logistics matter here. See full trail details, map, and current weather on OutsideAtlas for the most current information.
Open the Umatilla River Parkway trail page →Map, elevation profile, current weather, and OSM source.#3. Indian Race Track Trail #171
Indian Race Track Trail #171 earns the #3 spot for its sheer distance, though the exact mileage in OpenStreetMap data is a rough estimate. Expect 1,263 ft of gain on a forgiving grade. It earns its ranking on the data, but trail conditions can change quickly after storms or fire seasons, so verify before you commit a full day. Plan as a multi-day if you're not used to single-push 20+ mile days; resupply or shuttle logistics matter here. See full trail details, map, and current weather on OutsideAtlas for the most current information.
Open the Indian Race Track Trail #171 trail page →Map, elevation profile, current weather, and OSM source.#4. Little Huckleberry Trail #49
Little Huckleberry Trail #49 earns the #4 spot for its sheer distance, though the exact mileage in OpenStreetMap data is a rough estimate. Expect 1,785 ft of gain on a forgiving grade. Compared to similar trails in Oregon, this route trades difficulty for either solitude or scenery — sometimes both. Plan as a multi-day if you're not used to single-push 20+ mile days; resupply or shuttle logistics matter here. See full trail details, map, and current weather on OutsideAtlas for the most current information.
Open the Little Huckleberry Trail #49 trail page →Map, elevation profile, current weather, and OSM source.#5. Sandy Creek Covered Bridge
Sandy Creek Covered Bridge earns the #5 spot for its sheer distance, though the exact mileage in OpenStreetMap data is a rough estimate. Expect 233 ft of gain on a forgiving grade. What makes this one earn its spot on the list is the combination of mapped detail and the kind of through-and-through experience that justifies a longer drive. Plan as a multi-day if you're not used to single-push 20+ mile days; resupply or shuttle logistics matter here. See full trail details, map, and current weather on OutsideAtlas for the most current information.
Open the Sandy Creek Covered Bridge trail page →Map, elevation profile, current weather, and OSM source.#6. Sleeping Beauty Trail #37
Sleeping Beauty Trail #37 earns the #6 spot for its sheer distance, though the exact mileage in OpenStreetMap data is a rough estimate. Expect 1,401 ft of gain on a forgiving grade. Local trail-association reports tend to agree this is one of the better-maintained options in the area, which matters more on a hike of this length than on a quick walk. Plan as a multi-day if you're not used to single-push 20+ mile days; resupply or shuttle logistics matter here. See full trail details, map, and current weather on OutsideAtlas for the most current information.
Open the Sleeping Beauty Trail #37 trail page →Map, elevation profile, current weather, and OSM source.#7. East Crater Trail #48
East Crater Trail #48 earns the #7 spot for its sheer distance, though the exact mileage in OpenStreetMap data is a rough estimate. Expect 656 ft of gain on a forgiving grade. The route is well documented in OpenStreetMap, which is what put it on our radar — community-mapped routes tend to be the ones that get hiked enough to stay open. Plan as a multi-day if you're not used to single-push 20+ mile days; resupply or shuttle logistics matter here. See full trail details, map, and current weather on OutsideAtlas for the most current information.
Open the East Crater Trail #48 trail page →Map, elevation profile, current weather, and OSM source.#8. Shortcut Trail #171A
Shortcut Trail #171A earns the #8 spot for its sheer distance, though the exact mileage in OpenStreetMap data is a rough estimate. Expect 66 ft of gain on a forgiving grade. It earns its ranking on the data, but trail conditions can change quickly after storms or fire seasons, so verify before you commit a full day. Plan as a multi-day if you're not used to single-push 20+ mile days; resupply or shuttle logistics matter here. See full trail details, map, and current weather on OutsideAtlas for the most current information.
Open the Shortcut Trail #171A trail page →Map, elevation profile, current weather, and OSM source.#9. Timber-Wilson River Path
Timber-Wilson River Path earns the #9 spot for its sheer distance, though the exact mileage in OpenStreetMap data is a rough estimate. Expect 1,772 ft of gain, ground surface on a forgiving grade. Compared to similar trails in Oregon, this route trades difficulty for either solitude or scenery — sometimes both. The natural-surface tread can get slick after rain and muddy in spring — pick a dry weather window if you have the flexibility. Plan as a multi-day if you're not used to single-push 20+ mile days; resupply or shuttle logistics matter here. See full trail details, map, and current weather on OutsideAtlas for the most current information.
Open the Timber-Wilson River Path trail page →Map, elevation profile, current weather, and OSM source.#10. United States Congresswoman Darlene Hooley Pedestrian Bridge at Gibbs Street
United States Congresswoman Darlene Hooley Pedestrian Bridge at Gibbs Street earns the #10 spot for its sheer distance, though the exact mileage in OpenStreetMap data is a rough estimate. Expect paved surface on a forgiving grade. What makes this one earn its spot on the list is the combination of mapped detail and the kind of through-and-through experience that justifies a longer drive. A paved surface makes this one of the more accessible options on the list — good for strollers, mobility aids, and wet-weather days. Plan as a multi-day if you're not used to single-push 20+ mile days; resupply or shuttle logistics matter here. See full trail details, map, and current weather on OutsideAtlas for the most current information.
Open the United States Congresswoman Darlene Hooley Pedestrian Bridge at Gibbs Street trail page →Map, elevation profile, current weather, and OSM source.Planning your Oregon trip
A few pieces of context are worth keeping in mind specifically for Oregon. July-September for high Cascades; coast year-round; high desert spring and fall. Wildfire smoke, cold mountain water (hypothermia in summer creeks), and rapidly changing weather on Cascade summits.
Always cross-reference the official land-manager page before driving out — closures, fire restrictions, and seasonal road access can change quickly. Our trail pages link directly back to the OpenStreetMap source so you can see the tags we're working from.
If you're new to hiking generally, our beginner's guide covers footwear, layering, and the day-pack basics. For safety planning on bigger objectives, the ten essentials guide is worth twenty minutes of reading.
More Oregon hiking guides
If you found this useful, the rest of our Oregon coverage continues below.
- Steepest trails in Oregon — Hikes with the most elevation gain in the state.
- Best beginner hikes in Oregon — Easy, well-marked trails for first-time hikers.
- Most challenging hikes in Oregon — Expert-rated routes for experienced hikers only.
- Best national parks in Oregon — Federal parks and recreation areas ranked.
- Best waterfall hikes in Oregon — Trails leading to named falls, ranked by accessibility.
- Best dog-friendly hikes in Oregon — Where leashed dogs are explicitly welcome.
- Best family hikes in Oregon — Short, easy trails sized for kids and grandparents.
Rankings like this are starting points, not verdicts. Trail conditions change, new routes get tagged, and what was the toughest trail in Oregon last year might not be next year. We refresh these articles when the underlying data shifts meaningfully.
Got a correction, a route we missed, or a question? Drop us a note via the contact page. We read every email and we'd rather hear it from you than miss it.
