Occurring at roughly the same time as the naval battle off the coast was the landing of U.S. troops at Santiago. Among them we find Teddy Roosevelt and his band of Rough Riders, the 1st U.S. Volunteer Cavalry. The Rough Riders and various other units landed in Santiago and began making their way toward a prominent ridge just outside town called San Juan Hill, where the main Spanish fortifications sat. The battle lasted several days, but in the end Roosevelt and his Rough Riders famously charged and "took the hill," covering themselves in glory and gaining a prime spot in American military folklore.

Much of the battlefield is overgrown with scrub trees and rusting metal fences. Actually is a well-preserved park complete with cannons, an observation tower and the old Spanish trenches.