With the weather heating up in May, the history of the Seminole War usually sees a change as well. At this time of the year, both sides would show their resolve to either continue fighting, or calm down and not fight. The warmer weather would bring on the sickly season, and many forts in the interior of the state would often be abandon due to high rates of sickness among the soldiers. Planting season was bringing in the crops, and food had to be gathered by both Seminoles and settlers. For the Seminole and Miccosukee people, their annual gathering known as the Green Corn Ceremony was not far away.
On May 9, 1832, the Treaty of Paynes Landing is signed. No minutes of the proceedings were taken of the negotiations, and the chiefs who signed would later deny that they had signed or agreed to it. This treaty would forever be suspect of heavy-handed manipulation to bribe the Seminoles/Miccosukee into believing what they wanted in order to obtain their signature or mark.
In May of 1836, the 2nd Creek War heats up in Alabama and Georgia. Creek warriors destroy the town of Roanoke near the Chattahoochee River in south Georgia.
In May 1839, General Macomb says that he has reached an agreement to end hostilities, and that the 2nd Seminole War was over. The announcement is premature since not all the Seminole/Miccosukee had made this agreement, in particular the Spanish Indians and Miccosukee in south Florida who had no part of the talks with General Macomb. The truce is declared over when Col. Harney's trading post is attacked on the Caloosahatchee the following July.
On May 19, 1840, is the Battle of Bridgewater in Alachua County west of Micanopy, which is one of the deadliest skirmishes in the war for the soldiers.
On May 23, 1840, Miccosukee Indians under Wildcat attack a theater company on the St. Johns River and make off with the costumes.
On May 17, 1842, the last soldiers who are killed by Indians during the 2nd Seminole War. Two soldiers are killed near Fort Wacahoota, and another dies at Fort Fanning.
On May 4, 1858, Billy Bowlegs and his group of 165 Seminoles leave Florida. On May 8th, the War is declared over, ending approximately 60 years of hostilities between the United States and the Florida Indians.