The property which became Wakefield Farms was purchased in 1998 as a weekend escape from the hectic life of the city. The owners/innkeepers were raised on a farm and in a farming community even though they had lived their adult lives in cities. Thus, this property was found during the search for a respite from the city. The property consisted of approximately 35 acres and only the antique Greek Revival farmhouse existed on the tract. (The farmhouse had been moved to its current location from Bleiblerville via a short stay in Chappell Hill behind the Museum.) Then the barn, the pool and the Saltbox were added in order.

In 2001, adjacent property became available for sale and was incorporated into the initial tract. The expanded property quickly became more meaningful than an occasional get-away. By 2002, the owners/innkeepers made the complete move to the farm. Wakefield Farms was officially launched and named for the paternal grandmother of the innkeeper. In 2005, the decision was made to build a permanent residence on the 2nd tract of land and the Bed and Breakfast was expanded to include the Greek Revival Farmhouse. Since then, the property has been home to Registered Santa Gertrudis cattle, Boer goats, Dorper sheep and assorted chickens. Currently, only the goats, sheep and chickens are being run on the farm and overseen by the Great Pyrenees dogs and, of course, Molly, the German Short-Haired Pointer! Most recently, the Rosenwald School was moved in and restored to complete the village of the Bed & Breakfast!