RidgeSyncCort's Jester Loop
Cort's Jester Loop is a 2.4-mile loop in Mount Ascutney & the Connecticut River, Vermont, climbing 406 ft to a high point of 1,193 ft. It's rated easy, and most hikers need about 1.3 hours of moving time.
Every number on this page is computed from the trail-snapped route geometry and a real elevation profile, not estimated from a map. You can open the full route in RidgeSync to see the elevation profile against your own pace, add camps, and build it into a multi-day trip.
At 169 ft of gain per mile, this is gentler than most of Mount Ascutney & the Connecticut River, where the average is 249 ft per mile.
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Plan this routeHow hard is Cort's Jester Loop?
Cort's Jester Loop climbs 406 ft across 2.4 miles, averaging 169 ft of gain per mile — a gentle grade. It runs as a loop, so the return leg covers new ground rather than retracing the climb.
RidgeSync estimates moving time from the trail-snapped geometry and the real elevation profile rather than a flat miles-per-hour figure, which is why the estimate below is usually slower than a generic hiking calculator on steep New England tread.
Trailhead, parking and water
The route starts from a mapped parking area. Trailhead lots here are small — often a dozen cars or fewer — and the popular ones fill by 9am on summer weekends and through foliage season. An early start is a parking strategy as much as a weather one.
No mapped water sources sit within 0.75 mi of this route, so carry what you need for the full distance — generally two liters for a half day, and more in summer heat.
What you'll see
The route follows the Cort's Jester for its main stretch.
When to go
Topping out at 1,193 ft, this one stays below the 2,500 ft mud-season line, so it dries out earlier and is a reasonable choice in late spring when the high ground is still off-limits.
Late September through mid-October is the best window here: firm trail, no bugs, and the clearest air of the year. The dependable season runs late June through mid-October. Winter turns the steeper pitches into a traction problem — microspikes are the minimum, and north-facing sections hold ice well into spring.
Regulations and Leave No Trace
- Vermont asks hikers to stay off trails above 2,500 ft during mud season (roughly mid-April to Memorial Day) — this is a request, not a closure, and it is widely respected
- Dispersed camping on state land is generally legal below 2,500 ft, at least 200 ft from water and trails; the Green Mountain National Forest has its own rules and some areas are posted
- Campfires are prohibited at many Long Trail and Appalachian Trail sites — carry a stove and check the site before planning around a fire
- Dogs are allowed on most Vermont trails but must be under control; some summits with fragile alpine vegetation ask that dogs stay leashed
- Pack out everything, including food scraps and toilet paper — Vermont soil is thin and slow to break anything down
Frequently asked questions
How long does Cort's Jester Loop take?
Most hikers take about 1.3 hours of moving time for the full 2.4 miles, before breaks. Add an hour or more if you're stopping for lunch at the top or hiking with a group at mixed paces.
How hard is Cort's Jester Loop?
It's rated easy: 2.4 miles with 406 ft of elevation gain, or about 169 ft per mile.
How long is Cort's Jester Loop?
2.4 miles as a loop.
How high is Cort's Jester Loop?
The high point of this route is 1,193 ft.
Is there water on Cort's Jester Loop?
No mapped water sources sit within 0.75 mi of this route, so carry everything you'll need.
When is the best time to hike Cort's Jester Loop?
Late June through mid-October is the reliable window, with late September through mid-October usually the best of it. Because it stays below 2,500 ft, it opens earlier in spring than the high peaks.
Nearby hikes in Mount Ascutney
More like this
Near Ludlow, Woodstock, Killington
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Route data © OpenStreetMap contributors (ODbL). Elevation from USGS 3DEP / SRTM via AWS Terrain Tiles. Distances and elevation are computed from the route geometry, last rebuilt 2026-07-24.