“Back in the day,” more than 70 years ago, when Red Hook, NY, seemed as far away from New York City as one could get, Oakleigh Cookingham, the sheriff of Dutchess County, made a decision that has been a work in progress ever since.
Before he left the sheriff’s office, Cookingham purchased a 200-acre farm in Red Hook, located approximately 80 mi. north of New York City, in the Hudson Valley. From this farm, he expanded into the construction business, naming the company O.T. Cookingham Equipment Inc.
Over the years, O.T. Cookingham Equipment Inc. continued to grow and in 1945, after returning from World War II, Oakleigh Cookingham Jr., known as “Oak,” joined his father in the family business. In the late 1950s, he took over the company from his father.
In the early years, the Cookinghams used equipment from various manufacturers. The company’s first excavator was a Bucyrus-Erie model 22B cable-operated. It was a “great machine,” said Oak.
It wasn’t until the 1950s that they were introduced to Caterpillar and H.O. Penn Machinery by Doug Cochran and Dave Alexander, industry friends of Oak’s, who spoke well of Caterpillar and the service they received from H.O. Penn Machinery. Their recommendations enticed the Cookinghams into trying out Caterpillar equipment, beginning a relationship, which continues to this day.
The first Cat machine purchased by Oak was a brand new Cat D8. After many years of faithful service, it was sold at auction in 1987. That machine is still working today for Red Wing Sand & Gavel, a local aggregate producer.
Over the years, the Cookinghams’ preference for Caterpillar machines has not waned. Following Oak’s retirement, his son Oakleigh T. “Leigh” Cookingham III continued the tradition of buying Caterpillar equipment from H.O. Penn Machinery for his company Fastracs Inc. Leigh’s most recent purchase was a Cat 320C excavator, replacing a Cat EL200 machine. According to Leigh, this is the second 320C in his equipment fleet.
He said of the machines, “As always, they have performed to or exceeded our expectations.” As far as service from H.O. Penn Machinery, Leigh stated that “… [it] is always on the money.”
According to the Cookinghams, one aspect of the Caterpillar machines that is factored into the decision making process when facing a new purchase is the resale value. Leigh explained that they keep their machines longer than many other contractors, and yet, “When we go to sell or trade our old Cat machines, they still have value, whereas brand X machines would be worthless.”
As the Cookinghams have been loyal to Cat machinery and H.O. Penn, they too have faithful customers, including the Old Rhinebeck Aerodrome. The Aerodrome is a small grass airstrip that houses a fleet of vintage bi-planes and, during the summer months, hosts an air show. When the facility first opened in 1960, O.T. Cookingham Equipment Inc. was retained to do the clearing, as well as the cut and fill to build the original grass airstrip. Over the years, first Oak and then Leigh have continued to service the Aerodrome’s site work needs.
Oak believed that the most significant job he was involved in was the construction of Columbia County Route 11 in the 1960s.
“We were responsible for all aspects of that road from clearing to paving,” recalled Oak. “To this day, that stretch of highway is recognized with a scenic highway award.”
Another major project for Oak was the 1972 construction of the Maple Crest Dam in Windham, NY. The earth and flood control dam consumed approximately 1 million yds. of material.
When the Cookinghams started their business in Red Hook, it was a quiet place. Today however, construction and real estate development are on a continual upside as it becomes a bedroom community of the big city and the Cookingham family is there to help.
Just as the Cookinghams are seeing changes in their community, they also have seen many changes in the construction equipment they use. Oak said that both excavators and dozers advanced from cable operation to hydraulic operation in the 1950s. Later, Caterpillar introduced the high-track style final drive on dozers that helped eliminate final drive failure by doing away with shock load, which changed machine life expectancy and lowered maintenance costs.
Although there have been many changes for the Cookinghams and their equipment, one thing remains, it is still a family operation. Oak attributes the secret of the family’s success to its work ethic.
In addition, he stated, “Another key factor has been our employees. We have been very fortunate in finding dedicated people who represent us well, on and off the job site.”
Leigh added, “Finding the right people, paying them a good scale and keeping them happy so that they reflect well on the company is a major ingredient to our success.”