Old School House - Holly Tree Loop, Wye Island is a 2 mile loop trail located near Queenstown, MD and is good for all skill levels. The trail is primarily used for hiking and is accessible year-round.
Wye Island is a great place to go for a walk on the shore. We did the longer version of the loop which comes back by the Holly Tree (which really is pretty big!).
There is a very secluded area about half-way out to the water on this trail which is an open meadow area surrounded by newly planted trees and forest. A great place to eat your lunch.
We've done it with the entire family (12,10,6,2) and the trail was wide/easy enough for the jogging stroller the entire way.
The only hitch was when we stopped for water on top of a tick nest and found ourselves with 30+ on each of our legs after ~1 min of stopping! A little bit of freak-out from the younger ones but was fine after we kept moving.
They bush-hog all the trails on the island but this is done on an ad-hoc basis without prior-planning (I called to find out) so hitting them right after being mowed (which is the best time) will be a bit of luck.
We only did the section that runs straight to the water and back to the parking lot but it was a nice easy walk for me and my two small children. We will go back and do the full loop some other time, what a nice place this is. Lots of horses out and about when we were there and hunting is allowed here so mind what time of year it was.