Vermont's Green Mountains in early October are about as good as East Coast hiking gets — crisp air, clear skies and just enough chill to make the first climb feel welcome. That was the setting for a recent 25.4-mile out-and-back day hike up Glastenbury Mountain on the Appalachian Trail, starting from the Route 9 trailhead just outside Bennington.
The route follows a long, sustained climb of roughly 12.7 miles to the summit, with around 3,800 feet of ascent on the way up and about half that on the return. Early on, hikers pass Split Rock, where the AT threads straight through a three-foot gap in a split boulder — a small but memorable bit of trail engineering. Partially exposed viewpoints along the way offer occasional southern views, including a distant look at Mount Greylock over in Massachusetts.
The mountain's headline attraction, its historic fire tower, is currently off the menu. The lowest set of stairs was removed after a 2022 closure, and an inspection sign now warns of rust in critical structural joints. As tempting as a summit panorama might be, this is one to admire from the ground until repairs happen.
One thing worth knowing if you're planning a long-distance walk in this stretch: the logistics of resupply. The hiker ran into a southbound thru-hiker near the summit stuck in a classic trail headache — a resupply package waiting at the Bennington post office with no delivery confirmation, the post office closed the following day, and another box already sitting at a post office back up the trail. Losing days waiting on mail can wreck a schedule when you're hiking against a deadline. It's a good argument for either self-supporting your hike or building buffer days around any post-office-dependent resupply plan.
Late-season timing has its own character here. The stream of northbound thru-hikers has largely thinned out by early October, but the trail still sees southbounders, Long Trail hikers (which shares this corridor) and plenty of weekend backpackers making the most of Green Mountain National Forest. Locals at the trailhead were visibly surprised that Glastenbury could be done as a day hike — fair enough at 25 miles, though for most visitors the summit leg alone makes a solid outing.
For travellers, this is a great example of Vermont's accessible wild side: a serious mountain day under three hours' drive from the Boston–Albany corridor, with the town of Bennington nearby for food, lodging and trailhead parking. Just pack layers — early October can swing from glove weather at 7:30am to t-shirt conditions by mid-morning.
First published on The Trek.
