If you've already worked your way through the Vermont 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 7,954 mapped Vermont 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.
Vermont is dominated by the Green Mountains running its length — the Long Trail (272 miles, the oldest long-distance hiking trail in the US) crosses the state from Massachusetts to Canada. A full Long Trail thru-hike, the Long Trail Northern Section in winter, and the Catamount Trail (ski) are Vermont's defining endurance objectives. Black bears, rapidly changing weather on exposed ridges, and ice in shoulder seasons.
Our rankings here are data-driven — pulled from the 7,954 mapped entries OutsideAtlas tracks in Vermont — 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. Black Pond Bushwhack
Black Pond Bushwhack sits near Lincoln in Grafton 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 Black Pond Bushwhack trail page →Map, elevation profile, current weather, and OSM source.#3. Class III Rapids Portage
Class III Rapids Portage sits near Saint Johnsbury Center in Caledonia County and is rated expert — the #3 entry in a roster of hikes you don't take lightly. Tagged expert 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. 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.#4. Crescent View Trail
Crescent View Trail sits near Bow in Merrimack County and is rated expert — the #4 entry in a roster of hikes you don't take lightly. Expect dirt surface on a expert-only grade. Compared to similar trails in Vermont, 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 Crescent View Trail trail page →Map, elevation profile, current weather, and OSM source.#5. Dirt Jumps
Dirt Jumps sits near Williston in Chittenden 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 Dirt Jumps trail page →Map, elevation profile, current weather, and OSM source.#6. Free Ride
Free Ride sits near East Burke in Caledonia County and is rated expert — the #6 entry in a roster of hikes you don't take lightly. 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. 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.#7. Frog Rock Entry Head
Frog Rock Entry Head sits near Mont Vernon in Hillsborough County and is rated expert — the #7 entry in a roster of hikes you don't take lightly. 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. 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 Frog Rock Entry Head trail page →Map, elevation profile, current weather, and OSM source.#8. Great Hill Loop
Great Hill Loop sits near Bow in Merrimack County and is rated expert — the #8 entry in a roster of hikes you don't take lightly. 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. 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 Great Hill Loop trail page →Map, elevation profile, current weather, and OSM source.#9. Great Hill Loop
Great Hill Loop sits near Bow in Merrimack County and is rated expert — the #9 entry in a roster of hikes you don't take lightly. Expect dirt surface on a expert-only grade. Compared to similar trails in Vermont, 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 Great Hill Loop trail page →Map, elevation profile, current weather, and OSM source.#10. H. Laurence Achilles Trail
H. Laurence Achilles Trail sits near Shelburne in Chittenden County and is rated expert — the #10 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 H. Laurence Achilles Trail trail page →Map, elevation profile, current weather, and OSM source.Planning your Vermont trip
A few pieces of context are worth keeping in mind specifically for Vermont. June-October is the high-country window; mud season (April-May) is widely discouraged for trail use; foliage in late September is iconic. Black bears, rapidly changing weather on exposed ridges, and ice in shoulder seasons.
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 Vermont hiking guides
If you found this useful, the rest of our Vermont coverage continues below.
- Top 10 longest trails in Vermont — Multi-day routes and through-hikes ranked by distance.
- Steepest trails in Vermont — Hikes with the most elevation gain in the state.
- Best beginner hikes in Vermont — Easy, well-marked trails for first-time hikers.
- Best national parks in Vermont — Federal parks and recreation areas ranked.
- Best waterfall hikes in Vermont — Trails leading to named falls, ranked by accessibility.
- Best dog-friendly hikes in Vermont — Where leashed dogs are explicitly welcome.
- Best family hikes in Vermont — 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 Vermont 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.
