Sunday night remains cloudy and damp, with periods of rain, though heavy rainfall and localized flooding are not expected. Settled conditions return as damp weather improves on Monday before a reinforcing cold front moves across the region, sweeping through Long Island and ushering in a much colder Canadian air mass. Behind this frontal boundary, strong northwest winds will increase Monday night into Tuesday, creating breezy conditions on land and rough waters offshore where the National Weather Service indicates Small Craft Advisory conditions are likely on the ocean and possible for surrounding coastal waters.

Tuesday marks the arrival of the season's coolest air so far, with afternoon temperatures struggling to break out of the upper 50s and low 60s while nighttime lows drop sharply into the 40s. A crisp, breezy and dry fall pattern continues through Wednesday before temperatures begin a gradual recovery later in the week.

The main story is the transition to a much more fall-like pattern. Monday is transitional while Tuesday and Wednesday bring the coolest, driest air of the season so far. Temperatures should gradually begin recovering later in the week.