What is now Anamosa was founded as the settlement of Buffalo Forks in 1838 and incorporated as Lexington in 1856. Lexington was a popular name for towns at that time, so when Lexington chose to become incorporated as a city in 1877, the name was changed to Anamosa to avoid mail delivery confusion. There are many stories on how Anamosa was chosen as a name. Some believe it was named for a local Native American girl named Anamosa, meaining "white fawn", while others say it means "You walk with me."
The romantic origin of the naming of the town of Anamosa comes from its early history. A Native American family was passing through town in 1842. The family stayed at the Ford House. The little girl, named Anamosa, endeared herself to the townspeople and following the family's departure from town, local citizens decided to name their town after her.
The Wapsipinicon River flows through Anamosa. According to legend, a Native American maiden and her lover threw themselves off a bluff overlooking the Wapsipinicon River; one was named Wapsi, the other Pinicon. Origins of this legend are unconfirmed.
Anamosa was named the Pumpkin Capital of Iowa by the Iowa State Legislature in 1993 and hosts Pumpkinfest, a pumpkin festival and weigh-off, each October.
Anamosa was named the last over-night city for RAGBRAI XL for 2012.
The Anamosa Boot Hill Cemetery is still open today and is northwest of the town.