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. Cedar Creek Trail - South Moon Loop

Cedar Creek Trail - South Moon Loop ranks #1 for vertical gain, sitting near Ashland in Boone 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 Cedar Creek Trail - South Moon Loop trail page →Map, elevation profile, current weather, and OSM source.

#2. Jim Bridger Conservation Area Trail

Jim Bridger Conservation Area Trail ranks #2 for vertical gain, sitting near Blue Springs in Jackson County. 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. 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 Jim Bridger Conservation Area Trail trail page →Map, elevation profile, current weather, and OSM source.

#3. Ozark Trail - Eleven Point GREER

Ozark Trail - Eleven Point GREER ranks #3 for vertical gain, sitting near Alton in Oregon County. Expect dirt surface on a expert-only 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. 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 Ozark Trail - Eleven Point GREER trail page →Map, elevation profile, current weather, and OSM source.

#4. Piney Creek Wilderness Trail

Piney Creek Wilderness Trail ranks #4 for vertical gain, sitting near Cape Fair in Barry County. Expect ground surface on a genuinely demanding grade. Compared to similar trails in Missouri, 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. 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 Piney Creek Wilderness Trail trail page →Map, elevation profile, current weather, and OSM source.

#5. Horseshoe Lake Hiking Trail

Horseshoe Lake Hiking Trail ranks #5 for vertical gain, sitting near Granite City in Madison County. Expect earth surface on a expert-only 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. 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 Horseshoe Lake Hiking Trail trail page →Map, elevation profile, current weather, and OSM source.

#6. Customline (Downhill Only)

Customline (Downhill Only) ranks #6 for vertical gain, sitting near Leawood 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 Customline (Downhill Only) trail page →Map, elevation profile, current weather, and OSM source.

#7. Shin-Ga-Wa-Sa Nature Trail

Shin-Ga-Wa-Sa Nature Trail ranks #7 for vertical gain, sitting near Grandview in Jackson County. 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. 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 Shin-Ga-Wa-Sa Nature Trail trail page →Map, elevation profile, current weather, and OSM source.

#8. Tower Loop (Hollow) Trail

Tower Loop (Hollow) Trail ranks #8 for vertical gain, sitting near Cape Fair in Barry County. Expect ground 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. 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 Tower Loop (Hollow) Trail trail page →Map, elevation profile, current weather, and OSM source.

#9. River Bluff Nature Trail

River Bluff Nature Trail ranks #9 for vertical gain, sitting near Independence in Jackson County. Expect ground surface on a genuinely demanding grade. Compared to similar trails in Missouri, 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. 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 River Bluff Nature Trail trail page →Map, elevation profile, current weather, and OSM source.

#10. Jetpack - Downhill Only

Jetpack - Downhill Only ranks #10 for vertical gain, sitting near Leawood in Jackson County. Expect ground 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. 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 Jetpack - Downhill Only trail page →Map, elevation profile, current weather, and OSM source.

Planning your Missouri trip

A few pieces of context are worth keeping in mind specifically for Missouri. Spring and fall are best; summer is humid and tick-heavy; winter trails are quiet but ice-prone in shaded ravines. Copperheads and rattlesnakes in the Ozarks, ticks across the state, and flash floods in narrow river 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 Missouri hiking guides

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