RidgeSyncNeals Hill via Pine Drop
Neals Hill via Pine Drop is a 3.6-mile out-and-back in Woodstock & the Upper Valley, Vermont, climbing 581 ft to a high point of 1,306 ft. It's rated moderate, and most hikers need about 2 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.
Open Neals Hill via Pine Drop in the planner
Load the route, see the elevation profile against your own pace, add camps and water stops, and build it into a multi-day trip. Free, no account needed to try.
Plan this routeHow hard is Neals Hill via Pine Drop?
Neals Hill via Pine Drop climbs 581 ft across 3.6 miles, averaging 161 ft of gain per mile — a gentle grade. It's an out-and-back: 1.8 miles each way, and you get a second look at the same terrain on the descent.
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 start point is a trail junction rather than a formal lot, so check parking before you commit: roadside pull-offs are frequently posted, and town roads near trailheads are often unplowed or seasonally closed.
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 tops out at Neals Hill at 1,306 ft. Summits vary more than elevation suggests — some are open ledge with a full ridge view, others are wooded with a fire tower doing the work — so check what the top actually offers before counting on a view.
The route follows the Pine Drop for its main stretch.
When to go
Topping out at 1,306 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 Neals Hill via Pine Drop take?
Most hikers take about 2 hours of moving time for the full 3.6 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 Neals Hill via Pine Drop?
It's rated moderate: 3.6 miles with 581 ft of elevation gain, or about 161 ft per mile.
How long is Neals Hill via Pine Drop?
3.6 miles round trip — 1.8 miles each way as an out-and-back.
How high is Neals Hill?
The high point of this route is 1,306 ft.
Is there water on Neals Hill via Pine Drop?
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 Neals Hill via Pine Drop?
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 Upper Valley
More like this
Near Woodstock, Killington, Ludlow
Plan the trip
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.