Distance is one measure of a hike. Elevation gain is the one that decides how your legs feel the next morning. We pulled every trail in Vermont with a measurable elevation-gain tag — out of the 7,954 entries OutsideAtlas tracks here — and ranked them by total vertical. The result is a roster of climbs that punch above their mileage.
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. Mount Mansfield (4,393 ft, the state high) and Camel's Hump deliver Vermont's biggest gains. 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. Elevation-gain figures depend on the surveyor and the digital-elevation model used. Some trails are missing this tag entirely and are excluded from the list. Treat numbers as approximate but directionally reliable.
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. Appalachian Trail; Long Trail
Appalachian Trail; Long Trail ranks #1 for vertical gain, sitting near West Wardsboro in Windham 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 Appalachian Trail; Long Trail trail page →Map, elevation profile, current weather, and OSM source.#2. Appalachian Trail;Long Trail
Appalachian Trail;Long Trail ranks #2 for vertical gain, sitting near Manchester Center in Bennington County. Expect dirt 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 Appalachian Trail;Long Trail trail page →Map, elevation profile, current weather, and OSM source.#3. H. Laurence Achilles Trail
H. Laurence Achilles Trail ranks #3 for vertical gain, sitting near Shelburne in Chittenden 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 H. Laurence Achilles Trail trail page →Map, elevation profile, current weather, and OSM source.#4. LaPlatte Nature Park Trail
LaPlatte Nature Park Trail ranks #4 for vertical gain, sitting near Shelburne in Chittenden County. Expect ground 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. 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 LaPlatte Nature Park Trail trail page →Map, elevation profile, current weather, and OSM source.#5. South Summit Trail (white)
South Summit Trail (white) ranks #5 for vertical gain, sitting near Milford in Hillsborough 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 South Summit Trail (white) trail page →Map, elevation profile, current weather, and OSM source.#6. East Summit Trail (white)
East Summit Trail (white) ranks #6 for vertical gain, sitting near Milford in Hillsborough 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 East Summit Trail (white) trail page →Map, elevation profile, current weather, and OSM source.#7. North Boquet Summit Trail
North Boquet Summit Trail ranks #7 for vertical gain, sitting near Essex in Essex 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 North Boquet Summit Trail trail page →Map, elevation profile, current weather, and OSM source.#8. Piasecki Way South Loop
Piasecki Way South Loop ranks #8 for vertical gain, sitting near Enfield Center in Grafton 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 Piasecki Way South Loop trail page →Map, elevation profile, current weather, and OSM source.#9. Presidential Rail Trail
Presidential Rail Trail ranks #9 for vertical gain, sitting near Jefferson in Coos County. Expect gravel surface on a genuinely demanding grade. Compared to similar trails in Vermont, 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 Presidential Rail Trail trail page →Map, elevation profile, current weather, and OSM source.#10. Frog Rock Entry Head
Frog Rock Entry Head ranks #10 for vertical gain, sitting near Mont Vernon in Hillsborough County. 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. 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 Frog Rock Entry Head 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.
- Best beginner hikes in Vermont — Easy, well-marked trails for first-time hikers.
- Most challenging hikes in Vermont — Expert-rated routes for experienced hikers only.
- 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.
