Oldtown is the historic district of the city of Monkeytown, where the founders first settled. It has many historic buildings and landmarks, and quaint shopping streets. The district is bounded by Broadway to the southwest and South Main Street to the southeast. Notable locations in Oldtown include Monkeytown's first church, the city hall, and local cupcake bakery Monkeytown Cupcake. Monkeytown University is also located in Oldtown.
- Monkeytown City Hall
- Monkeytown Cupcake
- Our Lady of the Monkeys Catholic Church
- Monkeytown University
- Main article: List of Monkeytown residents