Rather than starting your adventure up this mountain at a remote trailhead, the trek up Mount Tom begins in a quaint New England village, complete with a town green and a bustling commercial scene. After grabbing a sandwich at one of the local delis, take a leisurely stroll up gradual switchbacks to views of the town and river below. This walk combines a gradual grade, excellent views, and proximity to ice cream to make it a great trip for first-timers, including toddlers.

This forest and the town’s green spaces have been preserved and restored over the centuries by concerned landowners, various land trusts, and the Billings Park Commission. The extensive trail network and opens spaces within the village of Woodstock are a testament to the power of collaboration and planning for the future. While Mount Tom was completely denuded in the 1800s, it is now home to a mature forest. Many New Englanders are used to young, dense forests filled with understory scrub, but a mature forest left in its natural state—like this one—will most likely have fewer, taller trees that block the sunlight and limit new growth, creating an open, park-like understory that
makes for easy travel and great views.

Faulkner Trail departs from the back of Faulkner Park, and the paved path quickly turns to gravel and dirt. This trail traverses across the contours of the mountain, climbing gently to the top, rather than just beelining straight up the grade to the summit. This makes for an easy and pleasant stroll for even the fussiest of young hikers. Play a game of Roving Hide and Seek, or try a game of Trail Bingo on your way up. The many park benches and a beautiful stone arch bridge give you plenty of interesting places to hide and items to look for. As you ascend, Lower Link Trail and Upper Link Trail will divert to your right—stay left at both of these intersections to reach the summit of Mount Tom. These link trails tie together an extensive network of footpaths that crosses Mounts Tom and Peg, Marsh-Billings-Rockefeller National Historical Park, the Vermont Land Trust’s King Farm, and other green space in Woodstock. Maintained by the Woodstock Trails Partnership, this network of more than 30 miles of trail offers opportunities to hike, crosscountry ski, and more. Find more information on Woodstock’s trails at nps.gov/mabi/planyourvisit/hiking-trails-walk-woodstock.htm; paper maps are available at the Billings Farm and Museum (see Plan B).

After several more wide switchbacks, the trail reaches a lookout point on your right (1.4 miles). A steep and rocky section a few hundred yards long brings you to the true summit (1.5 miles), wide-open and grassy, with views of Woodstock and the Ottauqueechee River Valley. Return the way you came.

The Billings Farm and Museum is both a working dairy farm and an exciting educational experience for the whole family, complete with jersey milk cows, draft horses, chickens, sheep, a farm museum, hands-on exhibits, butter churning, and ice cream. Visit billingsfarm.org for more information.
 

Woodstock is full of delis, pizza places, and fine dining to suit any taste.