As we've discussed at length, holidays, and the means of celebrating them, were very different during the colonial era. Most of the holidays that are enjoyed today were hardly even recognized by the first generation of American, due to the fact that they had a very different set of social and cultural norms.
As far as Valentine's Day is concerned, the differences are almost night and day. First off, colonial America did not celebrate Valentine's Day with chocolates and cards. This does not mean, however, that they were void of celebration. Instead of a formal Valentine's Day, many colonial Americans joined in celebrating festivities that were based on the Roman holiday of Lupercalia. Lupercalia was a holiday to commemorate both Romulus and Remus, the two fabled founders of Rome. During Lupercalia, men would chase women around in goat-skinned clothing, hoping to be able to catch a virgin. The women were also lightly whipped with leaves as they were chased. The men were to laugh as loud as possible, in the hopes of scaring away the evil spirits associated with winter (this would also supposedly aid in female fertility).
In addition to these festivities, young colonial women regulary pinned five bay leaves to their pillow (four leaves on each corner and one leaf in the middle). The belief was that the leaves would inspire the dreams of the young damsel, who would recognize her true valentine in her dreams. Young women also wrote the names of the village men on pieces of paper, which were then rolled into clay. The clays were then dropped into a vassel of water, where the women would wait for the first clay piece to rise to the water's surface. It was believed that the first clay piece to rise to the top was the young woman's true valentine.
Early Dutch settlers in the American colonies also celebrated a few Valentine's Day customs as well. The most popular tradition of young Dutch women was the belief that the first man she laid eyes upon on Valentine's Day was to be her future spouse. As a result, many young women would arise in the morning, keeping their eyes shut until a friend or family member advised them. It was usually planned by the family to have a pleasing male awaiting the young woman's first gaze. One can only imagine how much fun it would have been to play a practical joke on these helpess girls! =)