After distinction in studies at the College of William and Mary in Williamsburg, Virginia, Littlepage first went to Europe in 1780 under the head of the American delegation to Spain, John Jay. He fought and was wounded in the invasion of Minorca in 1781, while acting as a volunteer aide de camp to the Duc de Crillon. During the sea battle of the Great Siege of Gibraltar, Littlepage was an observer aboard the Spanish fleet; he made extensive notes and sketches that were well received at the Spanish court. The assault that took place however was a huge defeat for the Bourbon allies; Littlepage was on board a floating battery that was sunk, but he was saved. Subsequently in Cadiz, he met the Marquis de Lafayette with whom he journeyed to Paris in 1783. After a bitter dispute with John Jay over a perceived insult, Littlepage left Paris, on an expedition with the Prince of Nassau. He traveled to the Polish–Lithuanian Commonwealth, where he observed the Sejm session that took place in Grodno in 1784.