Is sailing the oldest American competitive sport?

This is a great question. Sailing is not the oldest American Sport. In fact, there are several "sports" or "competitive games" that Native Americans still regularly participate in today (e.g. Lacrosse) that are far older than competitive sailing. Early European sports imported by the first settlers would include Fencing and target shooting as well as Wrestling and boxing.

However, the Americas Cup Trophy is the oldest Trophy in sailing (1851), and many resources claim that it could quite possibly be the oldest perpetual trophy in any sport to date. Competitive sailing is a sport with a long history in the Americas. With any luck, it will last for hundreds perhaps thousands of years to come.