100 Years Strong!

H.O. Penn Celebrates Centennial Of Challenges and Achievements

POUGHKEEPSIE, NY—H.O. Penn staged a grand gathering at its headquarters here in early September to cap off the company’s ongoing centennial celebration in business. Scores of current and retired employees, executives and customers joined the festivities Sept. 7, which as one would expect was loaded with Caterpillar-sized fun. Tents were erected to serve up great food and live entertainment, and special events featured joyful activities for children as well as skills contests for those with the will and ambition to rise to the challenge. 

The main cast of actors stationed on the grounds included some of the latest and greatest equipment made by Caterpillar. And as a handshake with the past, many pieces of antique equipment were also on display to illustrate both the legacy and the progress made over the past 100 years.

Who We Are – H.O. Penn Machinery, Inc., with its more than 400 employees, is a premier Caterpillar dealer of machines, products and a vast inventory of parts to meet customers’ rental and equipment needs. With the addition of Metso crushers and screeners to its product offerings, H.O. Penn sells and services a spectrum of more than 900 Caterpillar machines at six locations throughout the region.

Equipment from yesteryear: construction machinery was on display, including this vintage pull-type Caterpillar grader on loan from Earthmovers Inc. of Danbury, CT. Photo Credit/CEG

Where We Are – Corporate headquarters in Poughkeepsie, NY, H.O. Penn now covers its service area with six location operations, five of which offer full sales and service for Caterpillar products.

  • The Newington, CT facility was opened in 1968.
  • The Poughkeepsie operation, originally established with the purchase of Poughkeepsie Farm Supply Co., was moved from Brickyard Hill on Route 44 to its current location in 1968. It was remodeled in 1995 when it became H.O. Penn’s corporate headquarters.
  • The Bronx, NY operations were relocated to the foot of the Whitestone Bridge in 1976.
  • The Holtsville, NY store was completed in 1982, replacing the Westbury location.
  • The Medford, NY location was subsequently opened to serve growing demand for Power Systems operations.
  • The Bloomingburg, NY location was opened in 2004 to service the needs of our customers west of the Hudson River.

In the Beginning… – In 1921, three businessmen, Hamilton O. Penn, Frank Ginsberg and E. Gwynn Robinson formed the Ginsberg-Penn Co. This firm, which was incorporated on Feb. 17, 1923, represented various manufacturers of construction and industrial equipment. The company was located in downtown Manhattan, in the Hudson Terminal, and in its earliest days sold mainly cement mixers, small shovels and paving machines.

The name of the firm was officially changed to H.O. Penn Machinery Company, Inc., in 1926. Shortly thereafter, Hamilton Penn moved operations from Manhattan to a new location in the Bronx. With continued growth and success, operations moved to the Port Morris Terminal at 140th Street and the East River in the Bronx on May 30, 1930. This location, which provided dock facilities and a private railroad siding, was the company’s headquarters until 1976 when the corporate offices were moved to Armonk, NY in Westchester.

From left, former CEO Tom Cleveland and the current CEO Rob Cleveland, representing the second and third generation of this family-owned business, greeted the crowd of current and former employees, customers and guests for the final celebration of the company’s centennial anniversary. Photo Credit/CEG
It was the granddaddy of birthday commemorations: Hundreds from across the lower- and mid-Hudson Valley joined the festivities at H.O. Penn’s headquarters in Poughkeepsie, NY in early September to celebrate the dealership’s 100th anniversary. Photo Credit/CEG
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