Highland Lake is a body of water located within the boundaries of Winchester, Connecticut.

[1] Highland Lake achieves its maximum depth of 63 feet (19 m) toward the center of Second Bay.

[4] The lake is popular for recreational purposes, including boating and fishing.

[3] Highland Lake is encircled by Wakefield Boulevard, which is a little over seven miles (11 km) long,[5] and its shores are heavily built up with residences (both seasonal and year-round) and dotted with many docks.

There have been several historical instances of small rogue wakes hitting the area between first and second bay.