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. Yeager's Cabin Connector to Wickersham Summit Trail

Yeager's Cabin Connector to Wickersham Summit Trail ranks #1 for vertical gain, sitting near Ester in Yukon-Koyukuk County. Expect unpaved 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 Yeager's Cabin Connector to Wickersham Summit Trail trail page →Map, elevation profile, current weather, and OSM source.

#2. Grande Denali Lodge & Denali Bluffs Hotel Connector Trail

Grande Denali Lodge & Denali Bluffs Hotel Connector Trail ranks #2 for vertical gain, sitting near Healy in Denali County. Tagged expert 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 Grande Denali Lodge & Denali Bluffs Hotel Connector Trail trail page →Map, elevation profile, current weather, and OSM source.

#3. Penguin Ridge Traverse Trail

Penguin Ridge Traverse Trail ranks #3 for vertical gain, sitting near Girdwood in Anchorage County. Expect dirt 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 Penguin Ridge Traverse Trail trail page →Map, elevation profile, current weather, and OSM source.

#4. Mt Reid South Scramble

Mt Reid South Scramble ranks #4 for vertical gain, sitting near Skagway in Skagway Hoonah Angoon County. Expect ground surface on a expert-only grade. Compared to similar trails in Alaska, 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 Mt Reid South Scramble trail page →Map, elevation profile, current weather, and OSM source.

#5. Soldiers Summit Trail

Soldiers Summit Trail ranks #5 for vertical gain, sitting near Yakutat in Yakutat County. Expect dirt 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 Soldiers Summit Trail trail page →Map, elevation profile, current weather, and OSM source.

#6. Dail Peak Scramble

Dail Peak Scramble ranks #6 for vertical gain, sitting near Skagway in Skagway Hoonah Angoon County. 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. 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 Dail Peak Scramble trail page →Map, elevation profile, current weather, and OSM source.

#7. Mt McNeil Scramble

Mt McNeil Scramble ranks #7 for vertical gain, sitting near Skagway in Skagway Hoonah Angoon 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 Mt McNeil Scramble trail page →Map, elevation profile, current weather, and OSM source.

#8. Denali View Trail

Denali View Trail ranks #8 for vertical gain, sitting near Anchorage in Anchorage County. Expect ground 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 Denali View Trail trail page →Map, elevation profile, current weather, and OSM source.

#9. Timberline Trail

Timberline Trail ranks #9 for vertical gain, sitting near Cantwell in Matanuska-Susitna County. Expect gravel surface on a genuinely demanding grade. Compared to similar trails in Alaska, this route trades difficulty for either solitude or scenery — sometimes both. A gravel-and-dirt tread holds up well after rain, though loose surface on descents calls for trekking poles or careful footing. 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 Timberline Trail trail page →Map, elevation profile, current weather, and OSM source.

#10. Girls Mountain Scramble Route

Girls Mountain Scramble Route ranks #10 for vertical gain, sitting near Valdez in Valdez-Cordova 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 Girls Mountain Scramble Route trail page →Map, elevation profile, current weather, and OSM source.

Planning your Alaska trip

A few pieces of context are worth keeping in mind specifically for Alaska. Summer (mid-June through August) is the only practical season for most routes; even then, snowfields linger above 3,000 feet. Bears (both grizzly and black), unbridged stream crossings, and rapidly changing weather are baseline hazards on any non-trivial route.

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 Alaska hiking guides

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