Woodstock is a such a beautiful, quaint village. One of the best ways to see the town is to hike in and around it. There are so many wonderful hikes right in the village of Woodstock, as well as within a short walking or driving distance that make great half or full-day adventures. Pack a picnic and head to the Pogue on Mt. Tom or the top of Mt. Peg for gorgeous views of our quintessential little village. It is only once you are are up in the mountains that you can truly take in the peace, tranquility and spectacular scenery that makes Vermont pure magic.
If you are in town and looking to go for an outdoor adventure, here are some of our favorite hikes in Woodstock for the most epic views and gorgeous scenic lookouts along the way.
The Best Hikes In Woodstock
Distance: 4-6 miles
Mount Tom is part of the Marsh-Billings-Rockefeller National Historic Park located within the Woodstock Village and surrounding land. There are several different trail systems throughout the park that are beautifully maintained and make for a wonderful hike. Different access points for hiking include from Faulkner Park, Old River Road (across from Billings Farm) or from Prosper Valley Road. For those not familiar with the area I would suggest taking the switchback trail from Faulkner or Old River Road. The trail from Old River Road is well groomed and accessible with a jogger while the Faulkner trail is a bit more rooted and not jogger friendly.
What is great about Mt. Tom is there are so many different options for your hike. Many hike to the Pogue, a beautiful 14-acre mountaintop pond and then head back down from there. While others make the full climb to the star at the very top. Depending on your route it is about 4 miles round trip to loop up from Billings Farm to the pogue, star and then back down again. A beautiful way to spend a morning or afternoon. Pack a picnic and enjoy it with a stunning view of the Woodstock Village from the top! Dogs are welcome on leash.
Distance: 1.3 miles
We love Mount Peg because you get the gorgeous sweeping view of the village, but it is such a quick and manageable hike. This is great for young kids that can’t walk too far, but also beware the trail is not jogger friendly. It is about 40 minutes round trip at a quick, steady pace. Again this is a great one to pack a picnic to enjoy at the top. There is also an awesome fire pit set up for those to use while in the area. Pack some s’mores and enjoy them with family or friends at the top as your consolation prize! Also important to mention, Mt. Peg actually has over 16 miles of groomed mountain bike trails for those looking for even more adventure! Dogs are welcome on leash.
Distance: 2.5 miles
This out-and-back trail is one of my favorites! A little more rugged, steep and challenging in parts than Mt. Peg and Mt. Tom I would only suggest this for older children. Dogs are welcome on leash. Luce’s Lookout is part of the Appalachian Trail which makes it a fun and unique way to be able to hike on a part of this well-known historic hiking trail. Luce’s Lookout culminates in an incredible view of Mt. Washington, Mt. Mansfield and Camels Hump. An old log cabin sits at the top with a guest book and a lookout if you are brave enough to climb the ladder to the top!
Distance: 4.4 miles
The Aqueduct Trails are another great place to base your hiking adventure in Woodstock. These trails are often less crowded than the more popular Mt. Tom and Mt. Peg, so if you are visiting on a busy day and looking for something a little more low key, The Aqueduct Trails are exactly what you need! This is another go to easy hike that is great for young kids. The trails lead to a pond, which you can then loop around and hike back on the original path. Also a popular mountain biking destination, don’t be surprised if you have a few bikers whiz by you on your hike. This is a rare place in town where well-behaved dogs are allowed off leash.
Eshqua Bog Natural Area
Distance: .5 miles
Not so much of a hike, but more of a stroll, the Eshqua Bog Natural Area is a beautiful place to visit while in Woodstock. Especially if you are visiting while the Lady Slippers bloom in June. There is a 460-foot boardwalk that you can explore to enjoy the Lady Slippers and other plant species in the bog below.
Ottauquechee River Trail
Distance: 2.8 miles
Head to Woodstock’s newly renovated outdoor space, East End Park and walk the Ottauquechee River Trail along the serene Ottauquechee River with river access points along the trail. The trail weaves through the fields and loops back around towards East End park. This is a great trail because it is flat and accessible to everyone. Jogger and kid friendly! Dogs are welcome on leash.
What are your favorite hikes in Woodstock? Let us know in the comments below!
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