When white settlers first bought the land now encompassing most of the Town of Riverhead in the late 1600s, they referred to the entire region as Aquebogue, an Indian word meaning “head of the bay” or “cove place.” Eventually, individual communities took on their own names such as Baiting Hollow and Jamesport. The hamlet known today as Aquebogue was settled about 1758. Frustrated at having to travel so far to annual town meetings held in Southold village, the early settlers of the Aquebogue area lobbied to split from Southold to create their own town. old trout brook millOn March 13, 1792, 
Southold was divided into two towns, Southold and Riverhead. Today Aquebogue is probably best known for its wineries and farm stands. But, in the 1840s, Aquebogue was known for its general store and its eagle-eyed proprietor, Benjamin Franklin Wells. When he wasn’t tending to his store or lumberyard, Wells was probably on the roof peering through a telescope at his lookout. He liked to watch for schooners coming up the bay carrying lumber that needed to be brought to his dock on Meetinghouse Creek.
old trailSince the late 1920s, an unusual roadside stand has stood on the south side of Route 25 in Aquebogue. Built as a vegetable stand, the wood-shingled structure resembles a miniature lighthouse and is often referred to as the “witch’s hat.” The property has changed hands several times and a number of items have been peddled there, from plants to Girl Scout cookies. Though somewhat rundown, the stand is still there, signaling to motorists headed east that they are entering North Fork turf.
