For over 40 years, Windy Hill has been a family-owned, family oriented company. Jack and Janice Shortt incorporated the business in 1976. Prior to that, they operated Hawaiian Flowers LTD, a retail florist business. After developing a wholesale plant business in the seven state midwest region, the business expanded to trucking after purchasing the Eustis, Florida terminal. In 1985, the Shortts sold the wholesale plant business to focus solely on growth within the transportation industry. In September 1999, Jack and Janice’s son, Eric Shortt, assumed management of the day-to-day operations of Windy Hill.

Today we maintain a fleet of 150 conventional tractors and 300 trailers. Our routes run from the Midwest to the Southeast, and we have a variety of trailers to handle many different types of freight. We pride ourselves on our ability to customize and adapt to our customer’s needs.

We’ve built our cornerstones on trust, communication, safety, and reliability. We’ve grown modestly over the past few decades, which has allowed us to maintain that 'small company' atmosphere. You’re not just a name to us, you’re part of the family.




Marshfield, Wisconsin

Eustis, FL 32736