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Intense tornadogenesis resulted when a supercell interacted with a sequence of prominent landforms on a day when the synoptic environment was favorable for supercell thunderstorm formation. Doppler radar observations show the storm was already supercellular but not tornadic while west of the Catskill Mountains, and that the storms mesocyclone intensified significantly as it passed over the eastern end of the Catskill escarpment and entered the Hudson Valley. Mesocyclone intensification and tornadogenesis appear closely related to the storms interaction with two separate terrain-channeled flows, both of which are clearly evident in Doppler velocity data. The initial 35-km track tornado (F2) dissipated when its parent mesocyclone weakened as it moved upslope into the Berkshires of western Massachusetts, before intensifying again in the Housatonic River Valley where tornadogenesis was repeated (F3), resulting in 3 fatalities at Great Barrington.