Hi So long as it isn’t wet weather, you would easily manage in tennis shoes / trainers. Path is well marked, you do have to watch your footing for tree roots and similar but that’s about it.

It is an easy hike from the parking lot off Prosper Road. Not too much elevation and what there is is gradual. The view is worth it!

It's doable on one of the trails, but not all of them. I can't recall the name of the trail we ascended on, it was much safer than the one we descended on.

Good morning! You drive over the old covered bridge almost across the street from the Woodstock Inn. You will see it when you enter the village green on the right side of the street. Travel through the bridge and go straight across until you are on the dirt road. Follow the short road. You are in the quaint neighbor hood. The park is on the right. You will see cars parked on the street. Park your auto and begin your trek by following the sign or path! I hope the leave begin to turn for you. Enjoy your beautiful hick.

I'm not sure either,but we stayed at the Woodstock Inn, right on the green in town, and the trail head we took was in the park right there. Then we came down the other side and walked back to the hotel from the other direction. Not sure where your Inn is located...but it was all fairly simple and close - lovely.