Orographic wind channeling, defined as dynamically and thermally induced processes that force wind to blow along the axis of a valley, is a common occurrence along the St. Lawrence River Valley (SLRV) in Quebec, Canada, and produces substantial observed weather impacts at stations along the valley, including Montreal (CYUL). Cold-season observed north-northeast (n = 55) and south-southeast (n = 16) surface wind events at CYUL are identified from 1979 to 2002. The authors partition the north-northeast wind events into four groups using manual synoptic typing. Types A and D (“inland cyclone” and “northwestern cyclone”) are associated with strong lower-tropospheric geostrophic warm-air advection and near-surface pressure-driven channeling of cold air from the north-northeast, along the axis of the SLRV. Type C (“anticyclone”) shows no evidence of a surface cyclone and thus is the least associated with inclement weather at CYUL, whereas type B (“coastal cyclone”) is associated with predominantly forced wind channeling along the SLRV. Type D of the north-northeast wind events and all south-southeast wind events exhibit similar sea level pressure patterns. The respective magnitudes of the pressure gradients in the Lake Champlain Valley south of CYUL and the SLRV play a large role in determining the favored wind direction. Soundings of the various event types illustrate substantial differences in temperature structure, with a large near-surface temperature inversion particularly prevalent in north-northeast events. The results of this study may provide guidance in forecasting winds, temperatures, and observed weather in and around the SLRV, given certain synoptic-scale regimes.