The core of Winedale is a collection of historic buildings, a project of preservationist and philanthropist Ima Hogg. Intermixed with four nineteenth-century buildings are a conference center, a dormitory, and a performance barn (theater). The University of Texas Center for American History administers the 225-acre site, located on part of a Stephen F. Austin land grant. The Winedale collections include furniture, equipment, and decorative art, much of it made locally by German immigrants.
The complex consists of a number of historic buildings moved to this site in the 1960s near the two original buildings: the c. 1834 Wagner House and the c. 1848 Four-Square Barn. Local surveyor and farmer Samuel K. Lewis built the house now known as the Wagner House, which envelops the earlier log house built c. 1834. Rudolph Melchior, an artisan immigrant from Magdeburg, Prussia, painted the interior floral and fruit designs in the late 1850s or early 1860s. Lewis died in 1867 and his heirs remained in the house until 1882 when they sold it to Joseph George Wagner Sr., a cobbler from Prussian Silesia. Four generations of the Wagner family lived in and expanded the house over the next eighty years. Other frame buildings include Hazel's Lone Oak Cottage (1854) and the MacGregor House (1859). The Theater Barn (1894) is a good example of adaptive reuse and hosts the annual Shakespeare at Winedale student performance each August by the university's English department.