The district is significant for its role in West Brookfield’s early history and development and in its agricultural and early industrial past. Preserved within the district are the remains of several grist and sawmill sites that recall three centuries of industrial use of area waterways as waterpower sites, from the 17th through the early 20th century. Several buildings and sites within the district are significant for their association with early West Brookfield families. The most numerous of these are associated with the pioneer Gilbert family, which played a key role in the development of the area from the early 18th century throughout the late 19th century.
The district is also significant as the least altered 19th century rural neighborhood in West Brookfield. Unlike other outlying areas of the town today, it still retains the open space and building distribution typical of the 19th century. It has well preserved examples of the simple, unadorned, vernacular architecture that was characteristic of West Brookfield farmhouses in that early period.
The Wickaboag Valley Historic District is listed on the National Register of Historic Places in 2000.