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Hiking in Woodstock at Mt Tom

From The Blog Rewarding Trails Near Woodstock, Vermont

Getting out for a hike up a mountain trail or stroll on a walking path is always more rewarding when your expedition leads to a payoff. Whether it’s a view that extends for miles, a magical waterfall, or rare and beautiful fauna, Vermont has trails to explore everywhere you look. In fact, right from the Woodstock Village you can hike two of our favorite mountains, Mt Tom and Mt Peg for beautiful views of the valley. And when you’re ready to explore further, you’re just a short drive away from easy boardwalk paths or challenging day hikes!

Eshqua Bog in Woodstock VT

Start with a Stroll

Eshqua Bog Natural Area - This boardwalk path and accompanying short walking loop opens up to a beautiful world of Vermont’s flourishing fauna. Just minutes from the Woodstock Village, the boardwalk is accessible and easy enough for the whole family – grandparents to toddlers – to explore the rare plant life that grows in the wetland. If you’re visiting in June, you may be lucky enough to see the delicate flowers known as lady’s slippers and the wild orchids! The short woodland path that skirts the bog area is a nice addition for an extra walk. Please note, dogs are not allowed in the natural area.

Thundering Falls, Killington
Melissa Madsen via All Trails

Thundering Falls, Killington – This easy trail that leads to a boardwalk along the large waterfall follows the only section of the Appalachian Trail that is wheelchair accessible. Though a quick path (less than ½ mile round trip), the payoff is huge! The approximately 125-foot falls cascades over metamorphic rock and is a favorite spot for nature photographers. If you’re looking for a longer hike, we recommend pairing this short stop with one of the longer hikes in Killington like Deer Leap Overlook, outlined below!

Deep Leap Overlook, Killington
Mary Orth via All Trails

Time for a Trek

Deer Leap Overlook – If you’re looking for a real day of hiking with a vast reward, you’ve got to start climbing! Gifford State Park in Killington, Vermont is just a short daytrip from Woodstock and holds some great hiking trails. This loop maps just under 5 miles and opens to a view of Pico Mountain from Deer Leap rock. Extend the hike even further and hitch onto the trail that snakes alongside Kent Pond before heading back to the trailhead.

Mountain Views from Ascutney, VT
Emily Bacon via All Trails

Mt. Ascutney Trails – The Mt. Ascutney State Park offers multiple trails to reach the summit, ranging in difficulty. On a clear day, you’ll love the reward of 360-degree views from the observation tower at the peak. Some lucky hikers have even been able to see out to Mt. Washington! Options for kid-friendly hiking or steep and rocky climbs make Mt. Ascutney a mountain for everyone. Some trails are even open year-round for a winter snowshoe climb.