The Lookout is well known by Woodstock locals, and provides a great and rewarding opportunity for a half-day’s outing. Although the Appalachian trail provides the access to this stunning viewpoint, The Lookout itself is on private land outside of the Appalachian trail corridor.
Once you get to The Lookout, upon breaking out of the woods at the end of a short spur off the Appalachian trail, you’ll find a weathered old cabin perched in a small rocky clearing. There’s a steep, wooden stairway that leads to an observation deck built on top of the cabin. From this deck, you get nearly 360 degrees of 100 mile Green Mountain views. Be sure and bring a lunch. This is a great spot for it.
To get to The Lookout from the Woodstock area, first drive to the nearest trailhead which is off Greengate Road.
From the October Country Inn, go to the center of Woodstock. Take Route 12 North about 3.5 miles to Wayside Rd. Turn left and follow this dirt road. You will come to a pond on your right. Turn right at this intersection. After 1.7 miles Wayside Road will bear to the left at the intersection with School House Hill Road and then turn into Greengate Road but you wouldn’t know it if you weren’t paying attention to the streetsigns. Another mile on Greengate Road and the road makes a sharp bend to the right.
On your left at this point, there’s an area that’s suitable for parking, and you’ll see a rutted, rocky, uphill trail leading into the woods beside a small brook. Now almost unrecognizable as a road, this trail used to be Lookout Farm Rd.
This trail gets rather rough in spots due to severe erosion. It will intersect with the Appalachian trail in about .4 of a mile. Before that, you will come to an intersection with an old gate leaning off to one side. Keep to your left. The trail comes into the AT at an angle forming a “Y” intersection, and you’ll bear to the right, following the AT in a southerly direction. Take a moment to mark this intersection in your mind so that you don’t miss it on your return.
Following the AT is pretty effortless. White blazes adorn the trees bordering the trail, and the trail itself is well worn, relatively flat, and easy to follow.
After almost a mile, the AT starts to climb in a more serious way, and soon after that makes a sharp turn to the left. The spur trail to The Lookout goes off to the right at this point. There’s a sign on a tree that marks The Lookout spur trail. A short .1 mile walk up the spur trail and you’re there.
Enjoy the view, and remember that this is private property that the owner’s have graciously allowed access to the public in order to enjoy this great spot. Please respect it.