The John L. Stam House was built in the late 185os by John and Louise Stam on property owned by Washington College.  John Stam was a wealthy entrepreneur who envisioned a “grand colonnade” lined with fine homes which would connect Washington College to downtown Chestertown.  Married to the daughter of the second president of the College (Colin Ferguson), he was in the position to negotiate a lease of the property from the College and build the first of those homes – what is today the John L. Stam House Bed and Breakfast.

Having a fondness for towers, John Stam chose a classic Gothic Revival Victorian design featured in architect Andrew Jackson Downing’s book Victorian Cottage Residences, and began building in 1857.  Three years later the home was completed.

During The Depression, the house was purchased at auction by Highe Hill who made it into a “tourist home” which it has been ever since.  Still retaining its original and unaltered floor plan on the first floor, the house has been meticulously restored by the current owners to preserve many of the original features.  Guests now enjoy the faux painted fireplaces, plastered ceilings, and faux wood graining originally envisioned by the Stam family, including  “Jenny Doors” which lead from the parlours to the veranda.