The hotel was greatly expanded in the 1920's adding an additional 210 rooms to its inventory. It was at this time that the building became known as the Hotel Woodruff.
The Woodruff's preeminence lasted for more than a century. The hotel began to suffer in the 1960's when passenger trains (which used to stop behind the Woodruff) ceased coming to Watertown. Also a factor in the hotel's decline was the building of modern hotels in Watertown, such as the Carriage House Inn on Washington Street and the Ramada Inn on outer Arsenal Street. All of the old downtown hotels suffered, and the Woodruff was no exception. After a slow decline that lasted for more than a decade, the Woodruff closed its doors in 1974 and was soon abandoned. After sitting vacant for two years, the city razed the structure in 1976.
Anthony Street, a one way road which ran under the Woodruff from Public Square to the current J.B. Wise Parking Lot, will be rebuilt in 2011 as part of the Public Square/J.B. Wise reconstruction project. This road will once again allow access to the parking lot from Public Square.
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