H.O. Penn Machinery Company is the Caterpillar Equipment dealer for the lower 13 counties of New York and the entire state of Connecticut. We have been in business for almost 100 years, and operate out of six locations, all of which offer full sales and service for Caterpillar products. Our locations are the corporate headquarters in Poughkeepsie, NY, Bronx, NY, Holtsville and Medford (Long Island), NY (the Medford location houses the Power Systems Corporate Headquarters), Bloomingburg, NY, and Newington, CT. H.O. Penn operates using its Managing By Values process, which differentiates us from other companies.

We are a family-owned company with an amazing organizational culture - that is values-driven and offers career advancement, development, and opportunity. We also take pride in offering competitive compensation and benefit packages, including benefits such as: medical, dental, vision, retirement, additional voluntary benefits, and union benefits for our union positions.

H.O. Penn, serving New York and Connecticut with the best in Caterpillar machines and equipment since 1923.