Windmill Trails is a 63-acre farm property near Tylertown, Mississippi with a history that reaches back more than 140 years. What began as a dairy farm later became timber land, and in 2020 Wilfred and Anna Barry began restoring the property for a new use without erasing what had already been here for generations.
Today, the farm includes two guest accommodations, horse facilities, pasture and many of the original features that first gave the property its character.
Check AvailabilityThe history of this land did not begin when it became a place for guests.
The farm is more than 140 years old. It first operated as a dairy farm. About 50 years ago, previous owners transitioned the property toward timber farming and planted pine trees across the land.
When Wilfred and Anna purchased the 63-acre tract in November 2020, they were taking on a property that already had its own agricultural history, existing buildings, mature trees and years of use behind it.
That history became the starting point for what came next.
Wilfred Barry grew up in Baton Rouge and spent his career in engineering. After graduating from the LSU College of Engineering, he joined his father's engineering firm and eventually became its sole proprietor. As retirement approached, Wilfred and Anna began looking for something different to take on.
Anna's connection to farm life started much earlier.
She spent part of her childhood on a small farm near Ragley, Louisiana, where animals, crops and daily farm chores were simply part of life. She and Wilfred later built their life together in Baton Rouge.
In 2020, that search brought them to rural Mississippi and the property that would become Windmill Trails.
The Windmill Trails property already had the structures that told its story.
Rather than remove everything and begin again, the renovation focused on working with what was already there.
The owners consulted Mississippi State University's Agricultural Extension as they planned improvements to the property. Existing farm buildings were then adapted for new uses.
The wood barn was renovated to include a loft and additional facilities. The former cinder block dairy shed became a guest house. The farmhouse was also renovated, including asbestos remediation.
These buildings did not have to stop being part of the farm's history simply because their purpose changed.
Wilfred Barry
Partner and Manager
Wilfred Barry was raised in Baton Rouge, as the youngest of four siblings. Following his graduation from LSU College of Engineering, he commenced his career at his father's engineering firm, SJB Group, LLC, starting as a junior project engineer. Over the years, he advanced through various roles until he became the sole proprietor. In 2023, Wilfred sold the business to an employee, marking the end of his 49-year tenure. In 2020, anticipating retirement, Wilfred and Anna sought new ventures. They found a rural property in Mississippi with significant acreage, a house, and a barn, setting the stage for their next chapter.
Anna Barry
Partner and the Inspiration
Anna spent a considerable part of her childhood on a small farm near Ragley, Louisiana, cherishing many fond and humorous memories of life on the farm. Growing up in a large family with numerous animals and crops, farm chores began before dawn and extended past dusk. Anna met Wilfred in 2007 while managing Submeter One, LLC, a company she owned in Baton Rouge. They married in 2013 and continued their journey together in Baton Rouge.
The Windmill Trails accommodations grew directly out of the property's earlier use.
The Barn Loft occupies the renovated wood barn, while the Dairy Cottage comes from the former dairy structure.
That connection matters because these are not newly built spaces designed to imitate a farm setting. They came from buildings that were already part of the property.
Guests can stay here while still seeing the pasture, trees, farm buildings and horses that make the place what it is.
View Our AccommodationsNot every part of the property needed a new purpose. Mature oaks and Loblolly pines remain across the land. At the center of the three main buildings stands a large live oak that has been certified by an arborist as more than 100 years old. Pasture also became an important part of the property again. After areas of wild growth were cleared, Bermuda grass was planted and steel fencing was installed. That pasture work was completed in 2021. The property also includes a raised herb and vegetable garden, an orchard and a chicken coop. The result is still recognizably a farm. Guest lodging is part of the property, but it does not replace the land around it.
Horses are not decoration here. Their presence affects how the property operates and why several guest policies exist. Windmill Trails horse lodging provides overnight facilities for travelers hauling horses through the Tylertown area. The property includes stalls, wash racks, fenced pasture, isolation paddocks and a round pen. Travelers specifically looking for overnight equine facilities can find the practical details on the Horse Motel page.
Book OnlineWindmill Trails is a farm property and adults only guest stay near Tylertown, Mississippi. The 63-acre property combines renovated farm buildings, two guest accommodations, horse facilities, pasture and land with more than a century of agricultural history. It is located at 436 Airline Hwy, Tylertown, MS 39667.
Windmill Trails is owned by Wilfred and Anna Barry. Wilfred grew up in Baton Rouge and spent his professional career in engineering after graduating from the LSU College of Engineering. Anna spent part of her childhood on a small farm near Ragley, Louisiana, where animals, crops and farm chores were part of everyday life. In 2020, as Wilfred approached retirement, they began looking for a rural property and purchased the 63-acre farm near Tylertown, Mississippi.
The farm is more than 140 years old. Its history began long before the current guest accommodations were created. The property originally operated as a dairy farm. About 50 years ago, previous owners shifted the land toward timber farming and planted pine trees. Wilfred and Anna Barry purchased the 63-acre tract in November 2020 and began renovating existing structures while retaining much of the agricultural character, mature trees and open land already present on the property.
Before guests stayed here, the property had already served several agricultural purposes. It began as a dairy farm and later transitioned toward timber farming. Existing structures included a wood barn, a cinder block dairy building and the farmhouse. During the renovation, the barn was adapted to include a loft and facilities, while the old dairy structure became a guest house. The current lodging therefore grew from buildings that were already part of the farm rather than replacing them with newly constructed imitation farm buildings.
Windmill Trails has two guest accommodations, the Barn Loft and Dairy Cottage. Each comes from an existing structure on the property. The Barn Loft is connected to the renovated wood barn, while the Dairy Cottage grew from the former dairy building. Guests can review the individual accommodation pages for the layout, amenities and booking details of each unit. Windmill Trails is adults only, cannot accommodate children due to horses on site, and does not allow pets.
Yes. Windmill Trails provides overnight horse lodging for travelers moving through the Tylertown area with horses and trailers. The equine facilities include up to four stalls, two wash racks, a 12-acre fenced pasture, three isolation paddocks and a round pen. RV and trailer hookups are also available. Because horse owners often need lodging close to their travel date, current stall and hookup availability should be confirmed directly before arrival through the Horse Motel information.
Windmill Trails is located at 436 Airline Hwy, Tylertown, MS 39667. The farm sits south of Tylertown and about two miles north of the Mississippi and Louisiana state line. That location makes the property accessible to guests visiting the Tylertown area as well as travelers coming from nearby Louisiana. Questions about a stay, the accommodations or current availability can also be directed to Windmill Trails at (225) 278-8934.
Windmill Trails did not begin as a vacation property. The dairy history, timber land, old barn, former dairy building, mature trees and pasture were already here.
The work since 2020 has been about finding useful new purposes for parts of the property while keeping its agricultural setting recognizable.
If that is the kind of place you want to stay near Tylertown, check the Barn Loft and Dairy Cottage for your dates.
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