Great Hikes near Woodstock Vermont

Columbus Day weekend usually turns out to be the prime time for foliage in Central Vermont. Tourists (including us) from all over the world descend on places like Woodstock Vermont to enjoy the foliage and outdoor activities. Peak foliage, however, is subject to the vagaries of nature. Since you have to make reservations well in advance during this time of year, you effectively place your bet and take your chances. Sometimes it works and sometimes it doesn’t.


Woodstock Vermont Hikes

Whether we were late or early for foliage, we love hiking the region’s many trails. Sure it often rains at this time of the year and trails could be muddy. But it is still enjoyable. Here are some of our favorite hikes.

  • Quechee Gorge Trail. We always enjoy this easy (165-foot elevation change), roughly 1.5-mile trail down a gorge formed by the Ottauquechee River 13,000 years ago, at the end of the last ice age. It follows the gorge downriver and backs up to a dam and small pond. We like to first view the gorge from the bridge above, looking at both sides of the gorge bridge before descending to the trail. You can walk in both directions. To the west, a dam flows into a small, but very pretty waterfall. To the east, the Ottaquechee River (which carved the gorge) leads to a riverbend whose side is laced with many layers of rock that have eroded at very different rates. You can make for a scenic, but difficult walk across the rugged shoreline. The elevation changes are small and the grades are relatively gradual.

Quechee Gorge 01Quechee Gorge 04Quechee Gorge 07

  • Mount Ascutney State Park. Mount Ascutney, a 3,144-foot monadnock, was the site of the first purpose-built hiking trail in the U.S. It has 5 trails that range from moderate to difficult. Be prepared to scramble over roots and rocks.
    • Mt. Ascutney Weatherfield Trail. We have made this 5.7-mile round trip, with a 2,200-foot elevation gain to the top of the tallest mountain in Eastern Vermont several times. We enjoy the lovely deep forest and during the right time of year, can find a variety of mushrooms and fungi on the trail. We learned to follow the trail markers as on one trip we forgot to follow rule one of hiking—if you lose the blazes, return the last one you saw and try again. Oops, we ended up losing the trail and had to use our compass and GPS to find our way. Apparently, we aren’t the only ones as others have commented about hard-to-fins blazes.
    • Mt. Ascutney State Park Summit Loop Trail.  Although we hiked the mountain from the base on a previous trip, this trip we took a shortcut—driving riving to within about 350 feet of the Summit on a Depression-era C.C.C. road. From there, we scaled the summit via a roughly 1.5-mile loop trail to the West Peak and on to the summit where a climb of an observation tower provided an impressive 360-degree view. We then took a rather rugged circuitous route down via the Castle Rock and the particularly impressive Brownsville Rock overlooks.


  • Mt. Tom is a modest-sized (1,340-foot) mountain behind the town of Woodstock. Depending on which trails you take, you go through tranquil forests, reach a wonderful view over the town and valley, and can explore the town’s 19th-century cemetery. We like taking a switchback-laden hike up the mountain’s face, and a tranquil saunter down the backside, past the Pogue (a pretty pond) and along tranquil carriage roads. You can also hike up the gradual switchbacks of the Faulkner Trail to the summit before descending the steep Precipice trail.

Mt Tom viewMt Tom 19Mt Tom deerDSC09574

  • Deer Leap Mountain. We took the 2.5-mile loop which has about a 600-foot elevation gain that takes you above the noisy car traffic and the trees. You get a three-directional birds-eye view of the section of the surrounding forests. The trail is a hazardous course with its rocks and roots but the views from the summit make it all worth it.
  • Mount Peg Loop, another abbreviated trail, this to the top of 1,100-foot Mt. Peg via a well-groomed 1.3-mile hiking/cross-country skiing loop that climbs about 350 feet to modest views. Once at the summit, the trail offers many other options, such as to a Nordic Ski Center or down to Woodstock.
  • Sherburne Trails are a complex of four interconnected trails through a pretty forest. We took two of the trails (Mind Eraser and Paco’s Path) totaling about 2 miles through the pastoral, colorful landscape.

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