Political map of North America & the Caribbean 28 December 1835 (Second Seminole War): The Seminole of Florida were the most independent of the Indian peoples marked for relocation to the west (Trail of Tears), having been at war with the US as late as 1823 (First Seminole War). Rather than accept forcible transfer, they chose to fight again (Second Seminole War) - moving out of their reservation in late 1835 to attack soldiers and settlements across Florida Territory. It took over a year for the US Army to gain the upper hand over the elusive Seminole, with the last bands holding out in the Everglades until 1842.