The Business of Trees: The West Wind Tree Farm by Debra Messick

If pandemic winter hibernation has you pining for spring, you are not alone. While perusing seed catalogs and sketching bedding plans sustains most growers, some stay active with more than garden variety flowers and veggies. Among the hardiest cold-weather warriors are Wes Gilbert and his six-man crew at West Wind Tree Farm in Preston and Hurlock, who brave the cold daily, painstakingly checking on each precious asset planted across approximately 300 pastoral acres.  

Since 1981, Wes’ late father Chuck had worked as a nursery man on Long Island.  But a growing passion for cultivating trees inspired his dream of starting an enterprise he could eventually hand down to his family. His search for a more favorable ecological and economic locale soon bore fruit. Familiar with and fond of the Eastern Shore from past hunting trips here, Chuck Gilbert found affordable, available land with room to grow.  

The local climate and soil seemed ideally suited for favorable plant acclimation, crucial to survival and successful growth, Wes Gilbert recalled. Though generally similar to Long Island in terms of temperature and proximity to water, the growing period here is a bit longer, with the first frost date usually occurring a little later, Betty Gilbert (Wes’ mom) added. Plus, it is far enough inland that the soil is not overly sandy.

By keeping the property’s original name, West Wind Farm, Chuck and Betty chose to honor the land’s legacy and reflect their own identity as more closely akin to family farm than amorphous “plant mart,” according to Wes.  Arriving in Preston in December of 2000, the couple rolled up their sleeves and “got up on tractors,” Betty recalled, starting small with just a few varieties including Leyland Cypress and Yoshino Cryptomeria, steadily expanding their range of offerings to include several types of Oak, Pine, Cedar, and Arborvitae plus River Birch, Beech, and Magnolia. (While his dad enjoyed branching out with experimental sowing of Southern Magnolias, Wes plans to maintain production of proven favorites for the foreseeable future.)  Among today’s top sellers are Green Giant Arborvitae and Crape Myrtle, he added.

West Wind’s mid-Atlantic location places the farm within affordable travel viability for buyers as far north as Massachusetts and as far south as the Carolinas. For those needing delivery, Gilbert contracts with local trucking companies to provide the service, supplying trailers. Many local landscapers and nurseries pick up directly from the farm.  Whether near or far, Wes strives to provide extensive experience marked by personal service and going the extra mile. “We mostly sell to wholesalers and landscapers. Sometimes I will sell to homeowners. It does not matter how many. It could be just one tree or many,” Wes Gilbert added.

Aged 21 when he first arrived to help his parents grow the farm, Wes’ first duties involved keeping the machinery up and running. Gradually he transitioned into the field, continuing his ad hoc apprenticeship with hands-on tree work. Over time he became his dad’s right hand, taking on more management responsibilities, training enabling him to step into the leadership role he’s provided since his dad’s passing. Patiently answering a persistently ringing phone in the office, he fields requests from customers who’ve grown to trust his experience and instincts. For long distance clients unable to select and tag prospective tree orders in person, Wes becomes a personal “finder”, locating exactly what they need and vouching for its well-being.  When making major decisions affecting the farm’s operation and future, he and mom Betty consult jointly.

On the land his dad foresaw as a family inheritance, Wes raises his 5-year-old daughter, in a community they all call home.  Over the years West Wind Tree Farm has seen a gradual increase in growth (including acquiring parcels in nearby Hurlock.) For now, though, the Gilberts are content to stay the course and maintain current size, with optimal quality and operational performance. 

To learn more, visit westwindtreefarm.com or call 410-310-8665.

Debra Messick is a retired Dorchester County Public Library associate and lifelong freelance writer. A transplanted native Philadelphian, she has enjoyed residing in Cambridge MD since 1995.