The Dover Library was organized as the Wonder Workers in 1898 and subsequently chartered as the Dover Plains Library Association by the state of New York in 1904. The Library is chartered to serve the population of the Town of Dover.

Over the years the Library has moved many times from a small brick building next to the Baptist Church, to Railroad Square News, and in 1979 to the Tabor-Wing House. The Library was open 25 hours per week with a certified librarian as its sole employee. The Town contributed $5000 for library support. In 1984, hours were expanded to 30 and a clerk was hired. In 1987, hours expanded again to 37.

On April 16, 2001, after it was determined that the Library was not meeting the recommended standards for the size of the community, the Dover Plains Library Association ultimately moved to the American Legion Building on Rt. 22 in Wingdale. Staff included one librarian and four part time clerks for 40 hours a week.  In November 2002, Town of Dover residents voted to put a fixed budget line in for the Library to receive $225,000 every year which allowed for an increase to 56 hours a week and more staff.

Today the Library has over 26,000 visits a year. The Library is open Monday thru Friday 10AM to 8PM and Saturday 10AM to 4PM.  Residents and visitors have access to computers and the internet, access to over 57,000 items in the collection such as books, audiobooks, DVDs and CDs, as well as the collections of the 66 libraries in the Mid-Hudson Library System, and engaging programs for all ages. The Library also maintains a Little Free Library at the Wiley Shelter that was installed in 2014, in support of Dover being part of an Appalachian Trail Community.