If you've already worked your way through the Indiana day-hike checklist, this is the list for what comes next. We ranked the state's hardest trails using a composite of difficulty tag (hard or expert), distance, and elevation gain, drawing from the 4,439 mapped Indiana trails in our database. These ten routes are reserved for hikers with the gear, the navigation skills, and the honesty about their own limits to tackle them safely.
Indiana's southern hills (Hoosier National Forest, Brown County) offer surprisingly steep terrain; the north is mostly flat farmland and Lake Michigan dunes. Full Knobstone traverses and serious Hoosier National Forest multi-day routes are Indiana's tougher tier. Copperheads and timber rattlesnakes in southern hills; ticks and mosquitoes statewide.
Our rankings here are data-driven — pulled from the 4,439 mapped entries OutsideAtlas tracks in Indiana — but the data has limits worth being honest about. A composite score weights expert and hard difficulty tags alongside total mileage and elevation gain. The result favors long, vertically aggressive routes with documented technical sections — there are surely tougher off-trail objectives in the state, but those are outside the scope of a trail directory.
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. Lake Shore Walk
Lake Shore Walk sits near Evansville in Vanderburgh County and is rated expert — our pick for the toughest trail on the list. Expect ground surface on a expert-only 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. Best attempted by hikers comfortable with long days, route-finding when the path gets faint, and weather that can turn fast. Not a casual outing. See full trail details, map, and current weather on OutsideAtlas for the most current information.
Open the Lake Shore Walk trail page →Map, elevation profile, current weather, and OSM source.#2. Mandrake Walk
Mandrake Walk sits near Evansville in Vanderburgh County and is rated expert — the #2 entry in a roster of hikes you don't take lightly. Expect ground surface on a expert-only 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. The natural-surface tread can get slick after rain and muddy in spring — pick a dry weather window if you have the flexibility. Best attempted by hikers comfortable with long days, route-finding when the path gets faint, and weather that can turn fast. Not a casual outing. See full trail details, map, and current weather on OutsideAtlas for the most current information.
Open the Mandrake Walk trail page →Map, elevation profile, current weather, and OSM source.#3. Purple
Purple sits near Mokena in Will County and is rated expert — the #3 entry in a roster of hikes you don't take lightly. 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. Best attempted by hikers comfortable with long days, route-finding when the path gets faint, and weather that can turn fast. Not a casual outing. See full trail details, map, and current weather on OutsideAtlas for the most current information.
Open the Purple trail page →Map, elevation profile, current weather, and OSM source.#4. Dunes Long Trail Alternates
Dunes Long Trail Alternates sits near Chesterton in Porter County and is rated hard — the #4 entry in a roster of hikes you don't take lightly. Tagged hard in OpenStreetMap. Compared to similar trails in Indiana, this route trades difficulty for either solitude or scenery — sometimes both. Best attempted by hikers comfortable with long days, route-finding when the path gets faint, and weather that can turn fast. Not a casual outing. 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.#5. Glidwell Trail
Glidwell Trail sits near Brookville in Franklin County and is rated hard — the #5 entry in a roster of hikes you don't take lightly. Tagged hard 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. Best attempted by hikers comfortable with long days, route-finding when the path gets faint, and weather that can turn fast. Not a casual outing. See full trail details, map, and current weather on OutsideAtlas for the most current information.
Open the Glidwell Trail trail page →Map, elevation profile, current weather, and OSM source.#6. Yellow Birch Ravine
Yellow Birch Ravine sits near Taswell in Crawford County and is rated hard — the #6 entry in a roster of hikes you don't take lightly. Expect earth 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. Best attempted by hikers comfortable with long days, route-finding when the path gets faint, and weather that can turn fast. Not a casual outing. See full trail details, map, and current weather on OutsideAtlas for the most current information.
Open the Yellow Birch Ravine trail page →Map, elevation profile, current weather, and OSM source.#7. Yellow Birch Ravine
Yellow Birch Ravine sits near Taswell in Crawford County and is rated hard — the #7 entry in a roster of hikes you don't take lightly. Expect earth surface on a genuinely demanding 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. Best attempted by hikers comfortable with long days, route-finding when the path gets faint, and weather that can turn fast. Not a casual outing. See full trail details, map, and current weather on OutsideAtlas for the most current information.
Open the Yellow Birch Ravine trail page →Map, elevation profile, current weather, and OSM source.#8. Yellow Birch Ravine
Yellow Birch Ravine sits near Taswell in Crawford County and is rated hard — the #8 entry in a roster of hikes you don't take lightly. Expect earth surface on a genuinely demanding 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. Best attempted by hikers comfortable with long days, route-finding when the path gets faint, and weather that can turn fast. Not a casual outing. See full trail details, map, and current weather on OutsideAtlas for the most current information.
Open the Yellow Birch Ravine trail page →Map, elevation profile, current weather, and OSM source.#9. Yellow Birch Ravine
Yellow Birch Ravine sits near Taswell in Crawford County and is rated hard — the #9 entry in a roster of hikes you don't take lightly. Expect earth surface on a genuinely demanding grade. Compared to similar trails in Indiana, this route trades difficulty for either solitude or scenery — sometimes both. Best attempted by hikers comfortable with long days, route-finding when the path gets faint, and weather that can turn fast. Not a casual outing. See full trail details, map, and current weather on OutsideAtlas for the most current information.
Open the Yellow Birch Ravine trail page →Map, elevation profile, current weather, and OSM source.#10. Yellow Birch Ravine
Yellow Birch Ravine sits near Taswell in Crawford County and is rated hard — the #10 entry in a roster of hikes you don't take lightly. Expect earth surface on a genuinely demanding 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. Best attempted by hikers comfortable with long days, route-finding when the path gets faint, and weather that can turn fast. Not a casual outing. See full trail details, map, and current weather on OutsideAtlas for the most current information.
Open the Yellow Birch Ravine trail page →Map, elevation profile, current weather, and OSM source.Planning your Indiana trip
A few pieces of context are worth keeping in mind specifically for Indiana. Spring and fall are prime; summer humidity is significant; winter trails are quiet but ice-prone in ravines. Copperheads and timber rattlesnakes in southern hills; ticks and mosquitoes statewide.
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 Indiana hiking guides
If you found this useful, the rest of our Indiana coverage continues below.
- Top 10 longest trails in Indiana — Multi-day routes and through-hikes ranked by distance.
- Steepest trails in Indiana — Hikes with the most elevation gain in the state.
- Best beginner hikes in Indiana — Easy, well-marked trails for first-time hikers.
- Best national parks in Indiana — Federal parks and recreation areas ranked.
- Best waterfall hikes in Indiana — Trails leading to named falls, ranked by accessibility.
- Best dog-friendly hikes in Indiana — Where leashed dogs are explicitly welcome.
- Best family hikes in Indiana — 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 Indiana 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.
