One of the best known traditions of the old Kelley House at Edgartown was its semi-annual entertainment of the Justice of the Superior Court and his suite on the occasion of the sittings of the court in and for the County of Dukes County at Edgartown. The sittings used to fall in April and September, and many stories are still told of Bill Kelley and how, on occasion, he took the judge on a tour of Chappaquiddick while the court stood in recess.
For many years the house opened in time for the spring sitting and closed after the fall sitting.