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. Resurrection River Trail-Upland Route

Resurrection River Trail-Upland Route ranks #3 for vertical gain, sitting near Cooper Landing in Kenai Peninsula 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 Resurrection River Trail-Upland Route trail page →Map, elevation profile, current weather, and OSM source.

#4. Tortilla Chip RockTrail Trail

Tortilla Chip RockTrail Trail ranks #4 for vertical gain, sitting near Indian in Anchorage County. Expect dirt 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 Tortilla Chip RockTrail Trail trail page →Map, elevation profile, current weather, and OSM source.

#5. Upper Huffman Snowmobile Exit

Upper Huffman Snowmobile Exit ranks #5 for vertical gain, sitting near Anchorage in Anchorage 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 Upper Huffman Snowmobile Exit trail page →Map, elevation profile, current weather, and OSM source.

#6. Penguin Ridge Traverse Trail

Penguin Ridge Traverse Trail ranks #6 for vertical gain, sitting near Girdwood in Anchorage County. Expect dirt 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 Penguin Ridge Traverse Trail trail page →Map, elevation profile, current weather, and OSM source.

#7. Ptarmigan Creek Cutoff Trail

Ptarmigan Creek Cutoff Trail ranks #7 for vertical gain, sitting near Cooper Landing in Kenai Peninsula County. Expect ground 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 Ptarmigan Creek Cutoff Trail trail page →Map, elevation profile, current weather, and OSM source.

#8. Sheep Thrills Ridge Trail

Sheep Thrills Ridge Trail ranks #8 for vertical gain, sitting near Indian 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 Sheep Thrills Ridge Trail trail page →Map, elevation profile, current weather, and OSM source.

#9. Cannonball Pass Bootpath

Cannonball Pass Bootpath ranks #9 for vertical gain, sitting near Hope in Kenai Peninsula County. Expect ground surface on a genuinely demanding 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 Cannonball Pass Bootpath trail page →Map, elevation profile, current weather, and OSM source.

#10. Heritage Falls / Polar Bear Valley Trail

Heritage Falls / Polar Bear Valley Trail ranks #10 for vertical gain, sitting near Eagle River in Anchorage 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 Heritage Falls / Polar Bear Valley Trail 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.