If you've already worked your way through the New York 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 58,943 mapped New York 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.
New York compresses Adirondack High Peaks, Catskills, Finger Lakes gorges, Long Island shoreline, and Hudson Highlands into one state. The Adirondacks alone are larger than several Western parks. The Adirondack 46, the Great Range Traverse, and a full Long Path thru-hike are New York's elite tests. Hypothermia in shoulder seasons (Adirondack weather changes fast), ticks (Lyme endemic), and slick rock on exposed High Peaks routes.
Our rankings here are data-driven — pulled from the 58,943 mapped entries OutsideAtlas tracks in New York — 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. A-Line Drop
A-Line Drop sits near Williston in Chittenden County and is rated expert — our pick for the toughest trail on the list. Tagged expert 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. 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 A-Line Drop trail page →Map, elevation profile, current weather, and OSM source.#2. Class III Rapids Portage
Class III Rapids Portage sits near Saint Johnsbury Center in Caledonia County and is rated expert — the #2 entry in a roster of hikes you don't take lightly. 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. 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 Class III Rapids Portage trail page →Map, elevation profile, current weather, and OSM source.#3. Dirt Jumps
Dirt Jumps sits near Williston in Chittenden County and is rated expert — the #3 entry in a roster of hikes you don't take lightly. 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. 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 Dirt Jumps trail page →Map, elevation profile, current weather, and OSM source.#4. Ebenezer Scramble
Ebenezer Scramble sits near Upper Jay in Essex County and is rated expert — the #4 entry in a roster of hikes you don't take lightly. Expect ground surface on a expert-only grade. Compared to similar trails in New York, 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. 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 Ebenezer Scramble trail page →Map, elevation profile, current weather, and OSM source.#5. Free Ride
Free Ride sits near East Burke in Caledonia County and is rated expert — the #5 entry in a roster of hikes you don't take lightly. Expect ground 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. 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 Free Ride trail page →Map, elevation profile, current weather, and OSM source.#6. Half Dome Trail
Half Dome Trail sits near Slate Run in Lycoming County and is rated expert — the #6 entry in a roster of hikes you don't take lightly. Expect dirt 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 Half Dome Trail trail page →Map, elevation profile, current weather, and OSM source.#7. Intergalactic Planetary
Intergalactic Planetary sits near Nesquehoning in Carbon County and is rated expert — the #7 entry in a roster of hikes you don't take lightly. Expect unpaved 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. A paved surface makes this one of the more accessible options on the list — good for strollers, mobility aids, and wet-weather days. 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 Intergalactic Planetary trail page →Map, elevation profile, current weather, and OSM source.#8. John Wert Path
John Wert Path sits near Boalsburg in Centre County and is rated expert — the #8 entry in a roster of hikes you don't take lightly. 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. 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 John Wert Path trail page →Map, elevation profile, current weather, and OSM source.#9. Knife Edge Trail
Knife Edge Trail sits near Sturbridge in Worcester County and is rated expert — the #9 entry in a roster of hikes you don't take lightly. Expect earth surface on a expert-only grade. Compared to similar trails in New York, 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 Knife Edge Trail trail page →Map, elevation profile, current weather, and OSM source.#10. Little Mount Washington Trail
Little Mount Washington Trail sits near Grantham in Sullivan County and is rated expert — the #10 entry in a roster of hikes you don't take lightly. 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. 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 Little Mount Washington Trail trail page →Map, elevation profile, current weather, and OSM source.Planning your New York trip
A few pieces of context are worth keeping in mind specifically for New York. May-October for high routes; black flies in late spring; fall foliage in early October is the visual peak. Hypothermia in shoulder seasons (Adirondack weather changes fast), ticks (Lyme endemic), and slick rock on exposed High Peaks routes.
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 New York hiking guides
If you found this useful, the rest of our New York coverage continues below.
- Top 10 longest trails in New York — Multi-day routes and through-hikes ranked by distance.
- Steepest trails in New York — Hikes with the most elevation gain in the state.
- Best beginner hikes in New York — Easy, well-marked trails for first-time hikers.
- Best national parks in New York — Federal parks and recreation areas ranked.
- Best waterfall hikes in New York — Trails leading to named falls, ranked by accessibility.
- Best dog-friendly hikes in New York — Where leashed dogs are explicitly welcome.
- Best family hikes in New York — 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 New York 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.
