Middletown, NY is a city located in Orange County. Its geographic highlights are the Walkill River and the Shawangunk Mountain Ridge.

Despite being a part of Orange County presently, Middletown was originally considered a part of Ulster County at its start in the late 1700s. According to the City of Middletown, NY government page, there is not a singular definite answer as to where Middletown got its name. General consensus is that it was likely given the name since it is a mid-point between the Delaware and Hudson rivers, or at least those settlements. During the early 1800s, Middletown saw many firsts between their first library and public school to their first chartered bank and newspaper. Middletown has a deep connection to the Civil War. You can find an original silk flag gifted to volunteers prior to fighting in battle during the Civil War. The flag was brought back to Middletown upon the return of those volunteers and currently rests with the Historical Society.

Today, Middletown is home to attractions like the Paramount Theater which holds live events and concerts. Exploring historic landmarks and the Galleria at Crystal Run are some top reasons visitors come to Middletown. There's also a growing brewery scene and many outdoor activities like hang gliding and hot air balloon festivals that draw attention to Middletown.