New ⁴⁰Ar/³⁹Ar ages for hornblende and muscovite from the Orange-Milford belt in southern Connecticut reflect cooling from Acadian amphibolite facies metamorphism between ∼380 to 360 Ma followed by retrograde recrystallization of fabric-forming muscovite and chlorite during lower greenschist facies Alleghanian transpression at ∼280 Ma. Reported field temperature and pressure gradients are improbably high for these rocks and a NW metamorphic field gradient climbing from chlorite-grade to staurolite-grade occurs over less than 5 km. Simple tilting cannot account for this compressed isograd spacing given the geothermal gradient of ∼20 °C/km present at the time of regional metamorphism. However, post-metamorphic transpression could effectively telescope the isograds by stretching the belt at an oblique angle to the isograd traces. Textures in the field and in thin section reveal several older prograde schistosities overprinted by lower greenschist facies fabrics. The late cleavages commonly occur at the scale of ∼100 μm and these samples contain multiple age populations of white mica. ⁴⁰Ar/³⁹Ar analysis of these poly-metamorphic samples with mixed muscovite populations yield climbing or U-shaped age spectra. The ages of the low temperature steps are late Paleozoic, while the ages of the older steps are late Devonian. These results support our petrologic interpretation that the younger cleavage developed under metamorphic conditions below the closure temperature for Ar diffusion in muscovite, that is, in the lower greenschist facies. The correlation of a younger regionally reproducible age population with a pervasive retrograde muscovite ± chlorite cleavage reveals an Alleghanian (∼280 Ma) overprint on the Acadian metamorphic gradient (∼380 Ma). Outcrop-scale structures including drag folds and imbricate boudins suggest that Alleghanian deformation and cleavage development occurred in response to dextral transpression along a northeast striking boundary. Alleghanian oblique collision of accreting terranes from the northeast would have resulted in northeast-southwest dextral transpression against the New York promontory. This deformation was responsible for crystallization of pervasive retrograde muscovite + chlorite cleavages and associated telescoping of the Acadian metamorphic isograds in southern Connecticut at ∼280 Ma.