The Metacomet Ridge continues northwest from Higby Mountain as Chauncey Peak and south as Besek Mountain. A line of smaller hills extends from the Higby Mountain ridgeline north into Middletown; most notable of these is Fall Hill from which tumbles the high Westfield Falls, visible from Interstate 91 just north of Higby Mountain. The north and east sides of Higby Mountain drain into Fall Brook, then Sawmill Brook, then the Mattabesett River, thence to the Connecticut River and Long Island Sound. The west and south side drain into Harbor Brook thence into the Quinnipiac River and Long Island Sound.