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Sixth-largest. Hagerstown is Maryland's sixth-largest city, with a population of just over 40,000 people. It is located in the western part of the state, near the border with Pennsylvania. The city is known for its historic downtown, which is home to many shops, restaurants, and museums. Hagerstown is also home to several colleges and universities, including Hagerstown Community College and the University of Maryland, Hagerstown.