On Tuesday July 27th my dog Tucker and I walked this trail for the first time. Altogether it was about 1 1/2 hours from the Housley Road trail head (near Best Buy) to the dam and back. This was an early and shady walk! Very fun. We encountered multiple walkers, runners and dog/owner teams along the way.
Here is an excerpt from the City of Annapolis web page for the Waterworks Park: The City of Annapolis and MORE created hundreds of acres of hiking and biking trails at and around Waterworks Park. You can ride or hike in to find 11 miles of trails! The Housley Loop is the most accessible loop. Public access and parking on Housley Road on the shoulder near the Stone Point Apartments. Look for the trailhead to your right in the woods on the left side of the stormwater drain. To note: the Defense Highway Connector trail connects the Housley Loop to the Defense Highway Parking Lot and Solar Park Loop. (Please do not park in the Defense Highway parking lot to access the trail as that lot is for permit holders only.) There is no fee to ride or hike these trails, but you have to get there on foot or by bicycle. Annapolis Waterworks Trail on Trailforks.