Conical masonry posts flanking the road marked the original main gate to the Vanderbilt farms: Oakland, owned jointly by Cornelius, Alfred G., and William H. Vanderbilt and, behind it toward the water, Sandy Point Farm, owned by Reginald C. Vanderbilt in the early twentieth century. Oakland's buildings—including a villa, a powerhouse, greenhouses, garages, a polo field, and an enclosed driving ring (the latter built by Alfred G. Vanderbilt when he was a leading horseman)—are all demolished, although one of the field gates, with conical masonry posts supporting gates in openwork timber, remains in near perfect condition.
Although the enclosed riding ring at Oakland Farm is gone, the one at Reginald Vanderbilt's Sandy Point Farm ring remains, actively used if in precarious condition. Shingled, with overblown Colonial Revival detail, it consists of three major parts. First, toward Sandy Point Avenue, a two-storied wing with what was once the principal entrance to the barn, through a passageway with tack rooms and stalls on either side and apartments for grooms overhead. Then the dirt ring itself, within a broad, column-free space spanned by scissor trusses, with more stalls and entrances to either side. At the far end is a viewing balcony, the first story painted white (although now dim) to contrast with the dusty wood tones elsewhere, and dignified with a few Neo-Colonial details, thus suggesting a mini-building within the big space. Its privileged audience once reached the balcony by way of a sunken formal garden at the far end of the barn, thence across a porch with a pergola and into a generous reception room with rustic fireplace and accompanying trophy room, kitchen, and other entertaining facilities. Behind the ring, and set a little apart from it, a water tower marks a barn courtyard in random stone and shingle with living quarters for workers upstairs. Faded though it is, the ring at Sandy Point deserves preservation as the most conspicuous monument remaining to the enthusiasm for horse shows during the golden years of Newport's high society.