Distance is one measure of a hike. Elevation gain is the one that decides how your legs feel the next morning. We pulled every trail in Illinois with a measurable elevation-gain tag — out of the 9,472 entries OutsideAtlas tracks here — and ranked them by total vertical. The result is a roster of climbs that punch above their mileage.
Illinois is mostly flat tallgrass prairie reshaped by agriculture — but Shawnee National Forest in the south and the canyon country at Starved Rock are dramatic exceptions. Charles Mound (1,235 ft) is the high point — vertical gain rankings here highlight Shawnee bluff trails and Starved Rock canyon climbs. Copperheads in the Shawnee uplands, ticks statewide, and flash floods in slot canyons after thunderstorms.
Our rankings here are data-driven — pulled from the 9,472 mapped entries OutsideAtlas tracks in Illinois — but the data has limits worth being honest about. Elevation-gain figures depend on the surveyor and the digital-elevation model used. Some trails are missing this tag entirely and are excluded from the list. Treat numbers as approximate but directionally reliable.
The Ranking
Ranked from #1 to #5. Click through any entry for the full trail page — map, elevation profile, weather forecast, and direct OpenStreetMap source link.
#1. Little Grand Canyon
Little Grand Canyon ranks #1 for vertical gain, sitting near Gorham in Jackson County. Expect ground surface on a genuinely demanding 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. The natural-surface tread can get slick after rain and muddy in spring — pick a dry weather window if you have the flexibility. Climbing fitness — not raw mileage — is the gating factor. Trekking poles and an early start pay off. See full trail details, map, and current weather on OutsideAtlas for the most current information.
Open the Little Grand Canyon trail page →Map, elevation profile, current weather, and OSM source.#2. Dunes Long Trail Alternates
Dunes Long Trail Alternates ranks #2 for vertical gain, sitting near Chesterton in Porter County. Tagged hard in OpenStreetMap. 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. Climbing fitness — not raw mileage — is the gating factor. Trekking poles and an early start pay off. See full trail details, map, and current weather on OutsideAtlas for the most current information.
Open the Dunes Long Trail Alternates trail page →Map, elevation profile, current weather, and OSM source.#3. r2r Start E'Town
r2r Start E'Town ranks #3 for vertical gain, sitting near Elizabethtown in Hardin County. Tagged expert in OpenStreetMap. 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. Climbing fitness — not raw mileage — is the gating factor. Trekking poles and an early start pay off. See full trail details, map, and current weather on OutsideAtlas for the most current information.
Open the r2r Start E'Town trail page →Map, elevation profile, current weather, and OSM source.#4. r2r guess 27
r2r guess 27 ranks #4 for vertical gain, sitting near Goreville in Johnson County. Tagged expert in OpenStreetMap. Compared to similar trails in Illinois, this route trades difficulty for either solitude or scenery — sometimes both. Climbing fitness — not raw mileage — is the gating factor. Trekking poles and an early start pay off. See full trail details, map, and current weather on OutsideAtlas for the most current information.
Open the r2r guess 27 trail page →Map, elevation profile, current weather, and OSM source.#5. R2R ???
R2R ??? ranks #5 for vertical gain, sitting near Makanda in Jackson County. Tagged expert in OpenStreetMap. 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. Climbing fitness — not raw mileage — is the gating factor. Trekking poles and an early start pay off. See full trail details, map, and current weather on OutsideAtlas for the most current information.
Open the R2R ??? trail page →Map, elevation profile, current weather, and OSM source.Planning your Illinois trip
A few pieces of context are worth keeping in mind specifically for Illinois. Spring and fall are best; summer is muggy and tick-heavy in the south; winter sees ice in Shawnee's sandstone canyons. Copperheads in the Shawnee uplands, ticks statewide, and flash floods in slot canyons after thunderstorms.
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 Illinois hiking guides
If you found this useful, the rest of our Illinois coverage continues below.
- Top 10 longest trails in Illinois — Multi-day routes and through-hikes ranked by distance.
- Best beginner hikes in Illinois — Easy, well-marked trails for first-time hikers.
- Most challenging hikes in Illinois — Expert-rated routes for experienced hikers only.
- Best national parks in Illinois — Federal parks and recreation areas ranked.
- Best waterfall hikes in Illinois — Trails leading to named falls, ranked by accessibility.
- Best dog-friendly hikes in Illinois — Where leashed dogs are explicitly welcome.
- Best family hikes in Illinois — 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 Illinois 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.
