The Windjammer Days Festival happens in two busy days that is packed with windjammers sailing to the Boothbay Harbor. It is a yearly festival that has served as a tradition that has been happening for more than four decades. The activities that happen during the event are all numerously interesting like pancakes for breakfast and a craft fair.

It also hold a parade that is joined by antique boats along with other shipyard tours and a street parade. There is a lot of musical entertainers performing with the huge fleet of visiting windjammers. The entire event ends with a huge fireworks extravagance. It is one of the best things that its visitors and participants look forward to see.