Overlook Mountain – NY

Wednesday, May 15th, 2019

I started out the day by having a short breakfast at Henry’s Diner in Burlington, VT. Good folks and good eats there.

I hopped on RT 7S and headed down to Woodstock, NY. I was meeting my elite hiking partner Brian at Overlook Mountain. The drive from VT to NY was nothing short of spectacular. You had the Adirondacks on the right side, and the White Mountains on the left side. As one Colchester local put it, Vermont is sitting in the middle of a big bowl of soup. The drive was very scenic. I went down RT 7S to 22AS to 4W to I-87S.

The 200 and some odd mile drive went by quick. I arrived to the trailhead at 1:30pm. Brian was there waiting and talking to an 80 year old hiker. Very cool.

I changed, and off we went. We headed up the path which was wide enough to fit utility vehicles. We found this beast parked about halfway up.

After one and half miles, we came to this abandoned hotel. Officially it was once the Overlook Mountain House in the late 1800’s. Two US Presidents have stayed there. It is said to be haunted. I found no such claim.

You can read the story at this link. https://cometowoodstock.com/2018/06/18/overlook-mountain-house/

After taking a few moments and photos at the hotel, we moved onward to the summit and fire tower. Whereas Brian went clear to the top of the tower, I only made it halfway up before feeling faint. Odd for me. I still managed to get some decent shots.

We then made our way from the fire tower over to the famed overlook cliff. From this view, you can see over the entire valley below including the Woodstock farm. This year is the 50th Anniversary of the historic festival.

Many people have etched their names into the cliff, but one crafty individual was skilled enough to etch in Old Glory.

We sat up there for a little while enjoying the view, and sharing stories with another hiker. We then made our way down. Just as we got to the parking lot, it started raining. Perfect timing. With just over 5 miles hiked, it was good to see my friend for at least one hike on this week long trip.

From here, we split ways as I was headed a few hours south to Peekskill, NY, and he was unfortunately headed back home. Until the next time!