HISTORY OF ORANGE
The tavern on this Turnpike has had a very checkered career.
WOODRUFF'S TAVERN, OR HALF-WAY HOUSE
The history of this property goes back to the early days of the town. There is no tradition that George Washington ever stopped there, but it is full of history.
The last name on the list of ''free planters'' of Milford is William East. Mr. East's first wife died, and in 1675 he married a widow, Mrs. Mary Plum. It was some of his estate which he gave to her that became the Tavern, or, as it is better known, Half-way House. Mary East left some property to her grandson, John Woodruff. In 1767 John conveyed his property to his son, Enoch, ''with my new house where Enoch now lives, at a place called Half- way Tree." So it would appear that the original house was built around 1767. When Enoch Woodruff's estate was distributed in 1787, he left dower rights in the house to his widow and to each of his four children. To his daughter, Polly, he left the ''bar room," and to both Polly and Anne were given ''a large quantity of rum,'' which suggests that the house may have been a public house before the Milford Turnpike was built in 1801. Polly (whose real name was Mary) married William Woodruff. It clearly appears that at that time the house had been built in three sections, the middle part being brick, and high up on the brick part the name of William Woodruff was painted in large letters. In the heyday of its existence, the Tavern was the scene of much gaiety, as frequent references are found concerning the balls and other social events held at Woodruff's Tavern.
After 1850 its popularity began to decline, for the railroad between Boston and New York was well established, so we assume the tavern business and coaching trade had greatly diminished. After 1812 this property, consisting of several pieces, including the tavern, changed hands twelve times, finally being acquired in 1897 by Arthur S. Crosby. He remodelled the house extensively and lived there for over forty years after which it was
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