Baiting Hollow, part of the Aquebogue purchase, was established in 1660 as it was divided into 60 lots. Named for the Hollow Pond and an inn owned by Jed or Gilbert Aldredge, horse and driver enjoyed rest and refreshment from their journeys. The old English word "bait" is defined as "to give food and drink, especially to horses on the road." The town did not see much activity until the late 18th century with the exception of the building of a cart path through the "Great Woods" which made travel from Brookhaven Town to Southold Town easier.
Baiting Hollow developed into a major farming town growing corn, potatoes, cauliflower and mulberry trees. As farmers would attempt to grow anything and everything, Baiting Hollow earned a reputation for experimental farming drawing agricultural specialists who studied plant diseases and destroying insects.