THE DISTINCTIVE CROSSING OF THE PINTA TRAIL AT THE GUADALUPE RIVER BECAME AN IMPORTANT LANDMARK OF THE HILL COUNTRY FRONTIER. IN OCTOBER 1839, A REPUBLIC OF TEXAS EXPEDITION GATHERED NEAR HERE TO SURVEY THE WESTERN BOUNDARY OF BASTROP COUNTY. BEXAR LAND DISTRICT CHIEF SURVEYOR WILLIAM LINDSEY WAS AMONG A GROUP OF ABOUT 120 SURVEYORS, TEXAS RANGERS, AND VOLUNTEERS LED BY COLONEL HENRY W. KARNES OUT OF SAN ANTONIO AND GALVESTON COUNTY SHERIFF WILLIAM F. WILSON. AFTER STACKING A PILE OF ROCKS EAST OF THE PINTA TRAIL ON THE NORTH BANK OF THE GUADALUPE RIVER TO MARK THEIR STARTING POINT, THE MEN SURVEYED A LINE FIFTY MILES LONG TO THE NORTHEAST THROUGH THE WILDERNESS. THEY REACHED THE COLORADO RIVER ON NOVEMBER 14. JOHN COFFEE (JACK) HAYS, RANGER AND SURVEYOR ON THIS EXPEDITION, RETURNED IN DECEMBER TO SURVEY LAND GRANTS TOTALING 49,676 ACRES, INCLUDING A 1,280-ACRE TRACT FOR SHERIFF WILSON SURROUNDING THE PINTA TRAIL CROSSING. HAYS USED LINDSEY’S ROCK PILE AS A SURVEY POINT, AND “PAINT ROAD” AND “PIENTAS TRAIL” APPEAR ON HIS FIELD NOTES. HAYS ALSO NAMED A NEARBY CREEK IN HONOR OF WILLIAM R. SISTY, WHO WAS KILLED ON THE EXPEDITION AND BECAME THE NAMESAKE OF SISTERDALE. JACK HAYS RETURNED TO THE AREA IN 1844 IN THE BATTLE OF WALKER’S CREEK, AN ENGAGEMENT BETWEEN TEXAS RANGERS AND COMANCHE. GERMAN IMMIGRANTS SETTLING FREDERICKSBURG IN THE 1840s ALSO UTILIZED THE RIVER CROSSING ON THEIR JOURNEY TO THEIR NEW HOME. NICOLAUS ZINK SETTLED ON WILSON’S 1,280-ACRE TRACT IN 1847, MAKING HIM THE FIRST RESIDENT OF SISTERDALE AND ALSO THE PIONEER SETTLER OF LATER-ORGANIZED BLANCO AND KENDALL COUNTIES. THE HISTORIC RIVER CROSSING NEAR HIS HOMESTEAD IS REMEMBERED FOR ITS ROLE IN MANY OF THE REGION’S MOST SIGNIFICANT HISTORICAL EVENTS AND DEVELOPMENTS. (2019)