The hike from the Skylight Pond Trail Head brings you to the Long Trail within 500' of the Skyline Lodge and within a mile of Battel and Bread Loaf Mountains. The hike described is an out and back along the LT north bound to Bread Loaf and Mount Wilson. Overall distance is ~9 miles with about 2650' of elevation gain/loss. This is a very long day hike and quite tiring, it may make sense to make use of the Skyline Lodge Shelter or the Emily Proctor Shelter (positioned midway between Bread Loaf and Wilson). Book time is ~7.5 hours non stop. I've done this in closer to 5.5 but it takes a lot of energy.
Take Route 125 East from the Junction with Route 7 in Middleburry VT. Pass through the town of Ripton and turn left at the second FS 59 road sign labeled Steam Mill Road. Take this unpaved road a little over 4 miles to a sharp left bend where there is a marked parking area down a short dirt road to the right, that will hold 25 cars. The trail head is here.
The Skylight Pond Trail is apparent when there is no snow on the ground. There is an infrequent blue blazing but the well packed earth and cut trail in most cases will be enough. In the winter it will be difficult to follow this trail.
Follow it 2.6 miles and gain ~1500' till it intersects with the Long Trail. The lower 1.3 miles is fairly flat with a few stream crossings and a single bridge (there is no water unless it's been raining or a recent melt out above this point until you reach the shelters). The upper 1.3 miles is loaded with sweeping switch backs so the trail never gets very steep.
At the LT intersection if you go straight you can reach the Skyline Lodge which also has a water source (.1 miles ahead). Turn left here (North) which climbs an additional 400' and at 1 mile you will reach Mount Wilson which is at a hair pin turn in the LT (a side trail will take you to the top and an overlook). There is nothing remarkable about the top but the overlook has a nice view. Back track to the LT and follow it North (actually goes somewhat Southeast).
In another half mile you'll approach the Emily Proctor Shelter and another water source. The LT is the trail to your right, Emily Procter Loop goes to the left. Stay on the LT north for another half mile and climb about 300' to the top of Mount Wilson. Again there is a slight view and you'll turn around here.
Retrace your steps to return.
Hiking poles help for the way down. DEET is nice because the bugs are out of control on the always damp LT. Winter is difficult and will require snowshoes/crampons depending on conditions and an ice axe. Access on FS 59 is questionable in the winter too.
External LinksGreen Mountain Club Shelters on LT
125 to FS59 Turn N43.95604 W72.99660 1380 ft
Bread Loaf Mountain N44.00222 W72.94141 3835 ft
Emily Proctor Shelter N44.00136 W72.93222 3412 ft
Mount Wilson N44.00471 W72.92587 3740 ft
Skyline Lodge N43.98694 W72.93643 3412 ft
Skylight Trail Head N43.99201 W72.96495 1969 ft
Junction SL/LTSL_LT N43.98867 W72.93757 3265 ft