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405 Main Street 
Princess Anne, Maryland
( Somerset Co ).
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Preston Theatre, Princess Anne Md 2013. Sorry for the tree, some things we just don't have control over.
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Over the years, there have been five theatre names associated with the Eastern Shore town of Princess Anne :

     in 1904, a Opera House was located at 404-405 Main Street (Later Somerset) , the building housing both a Opera House and Lodge.

    By 1911, maps show the Opera House being located on the second floor of the same building, with stores occupying the first floor. Behind the building was a small bowling alley at 372 Church Street. Next to the Opera House was a carriage and wagon sales and service business.

    1923 gets a little confusing, with two insurance maps for the same date showing different things. One shows the Opera House at 404 Main Street showing movies on the second floor, , next to the Bank of Somerset (406 Somerset). The Post Office was located next to the theater. The second Insurance map Shows the Opera House building being used as a post office, restaurant and bowling alley. That map also shows the Preston Theatre a block away at 363 Somerset.

    In the early 1930's, The Auditorium Theatre was listed in Somerset Avenue ( apparently also listed as 404 Main Street as well ) . The Auditorium was listed as late as 1945 , and seated between 250 and 300 people. From what we can tell, the old Auditorium Theatre as well as the bowling alley that was next to it have been torn down. The same block also housed the old Opera House, and the theatre might have been part of that as well. 
 
  In 1931, there was a listing for the New Preston Theatre, and that theatre was listed through atleast 1937. It seated 500 people. In 1938, the Preston Theatre was listed ( likely the New Preston Theatre renamed ) , located at 363 Somerset Avenue , and it continued to show listings through 1947, seating 400 people. In 1946, The Princess Theatre was listed, located at 405 Main Street ( Somerset Avenue ) , listed through the 1950's. In 1952, the Arcade Theatre was also listed on Somerset Avenue, seating 400 .

    A check of a 1923 Insurance Map shows the town theatre , complete with bowling in the back, next to a bank , between Prince William and Washington Streets . 
 
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Any information of the history of movie houses in Princess Anne would be greatly appreciated.