In the 1840s, at the height of his legendary career, Daniel Webster made annual fall shooting trips to Quogue and Westhampton, staying regularly at the Hallock House, then run by Orlando Hallock. The inn thrived during the Boarding House Era (1870 – 1940), when Quogue was one of the first of the developing summer resort communities along Long Island’s beautiful south shore and boarding houses proliferated as the primary source of local public hospitality.
In 1871 the building was renovated and enlarged by John Dayton Hallock to accommodate 45 guests. He then built a private cottage for his family in 1889, and in 1893, with the growing success of his business, constructed another cottage to rent. These additional cottages were built to the rear of the Hallock House, whose property then ran down to the canal (now the Intercoastal Waterway) on both sides of Quogo Neck Lane.