The Ranking

Ranked from #1 to #6. Click through any entry for the full trail page — map, elevation profile, weather forecast, and direct OpenStreetMap source link.

#1. Presidential Trail

Presidential Trail ranks #1 for vertical gain, sitting near Hill City in Pennington County. Expect concrete 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. A paved surface makes this one of the more accessible options on the list — good for strollers, mobility aids, and wet-weather days. 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 Presidential Trail trail page →Map, elevation profile, current weather, and OSM source.

#2. Cabin Trail

Cabin Trail ranks #2 for vertical gain, sitting near Marsland in Dawes County. Expect dirt 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. 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 Cabin Trail trail page →Map, elevation profile, current weather, and OSM source.

#3. Old Baldy Summit Trail

Old Baldy Summit Trail ranks #3 for vertical gain, sitting near Spearfish in Lawrence County. Tagged hard 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 Old Baldy Summit Trail trail page →Map, elevation profile, current weather, and OSM source.

#4. Saddle Pass Trail

Saddle Pass Trail ranks #4 for vertical gain, sitting near Interior in Jackson County. Tagged hard in OpenStreetMap. Compared to similar trails in South Dakota, 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 Saddle Pass Trail trail page →Map, elevation profile, current weather, and OSM source.

#5. Spire access

Spire access ranks #5 for vertical gain, sitting near Hill City in Custer County. 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. 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 Spire access trail page →Map, elevation profile, current weather, and OSM source.

#6. Deer Run

Deer Run ranks #6 for vertical gain, sitting near North Sioux City in Woodbury County. Tagged hard in OpenStreetMap. 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. 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 Deer Run trail page →Map, elevation profile, current weather, and OSM source.

Planning your South Dakota trip

A few pieces of context are worth keeping in mind specifically for South Dakota. May-October is the practical window; winters bring serious cold and blizzards; afternoon thunderstorms are common in summer. Lightning on exposed peaks, bison in Custer SP and Wind Cave NP, and rattlesnakes in the lower Badlands.

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 South Dakota hiking guides

If you found this useful, the rest of our South Dakota coverage continues below.