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Mark-Your-Calendar-Now Events

So, wait…being on an island isn’t enough reason to visit? Ok, here’s a list of our Top 5 island events that may be worth buying a calendar for. (Or perhaps bookmark this one at

New Year’s Eve at the Bay – September 17th

This long-standing island tradition benefits the Chamber of Commerce…and everyone who partakes. With Monte Carlo games, hats, and favors, you can ring in the New Year island-style—in September.

Wine Fest – October 1st

In addition to winery tours and a large silent auction, you can sample more than 200 foreign and domestic wines. Decisions, decisions…

Maritime Celebration – June 17th – 20th

Bring your brood and welcome the US Brig Niagara, get hands-on sail experience, and celebrate the summer on the island. Need another reason? It’s the same 4 days as Pyrate Fest.

Oktoberfest – October 8th – 9th

Jet Express recommendations for a perfect Oktoberfest celebration.

Hot spiced wine. Cold beer. Plus live polka and German music, dancers and plenty of German-style flavor and food. Experience it once, and you’ll return every year for this stein-raising island event.

Pyrate Fest – June 17th – 20th

This family friendly event is rated ARRRRGH. It kicks off with “Booms over the Bay” and continues with 4 days of swashbuckling events—like kids and adult costume contests, a charity-driven Pyrate Run and more. So grab your family, Pyrate up, and party down.