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Annual Events

Experience the best of Pleasant Prairie by attending one of our unique annual events. From holiday celebrations that bring everyone together to outdoor events that showcase the natural beauty of our slice of Wisconsin, annual events in Pleasant Prairie let you get to know the Village from a festive perspective.

Events That Mark the Season

In June, the annual Pleasant Prairie Triathlon brings triathletes from all over the Midwest to challenge themselves amongst the greenery and mild weather found here in the summer. This monumental race combines a swim through spring-fed Lake Andrea, a bike ride along picturesque roads, and a run through Prairie Springs Park on both paved and gravel roads for a day of heart-pounding fun. Kids can also go for the gold at the Pleasant Prairie Junior Triathlon. In August, the Iron Girl Triathlon empowers female athletes of all experience levels, including kids.

The end of summer brings Lake Andrea Dragonfest. Held each August, Dragonfest is a community dragon boat race, each stunning vessel holding a team of 22 rowers. Not to be missed!

No year is complete without a trip to the award-winning Bristol Renaissance Faire. This summer renaissance faire is an immersive experience of food, rides, costumes, and live entertainment. Visit more than once as special themed weekends mean you’ll never have the same experience twice at the Bristol Renaissance Faire!

As fall approaches, nothing pairs better than a pumpkin spice latte while browsing the BEST deals at the Pleasant Prairie Premium Outlets. With impressive savings at over 90 stores, it is the obvious Back-To-School and Black Friday holiday shopping destination.

Pleasant Prairie celebrates the end of the holiday season in a big way at the annual Twelfth Night Holiday Tree Bonfire. This isn’t a little backyard pit fire, this is a HUGE bonfire full of used pine Christmas trees. Join us in giving the holidays one last hurrah over treats and hot chocolate surrounded by friends new and old as we bid the season farewell.

Pleasant Prairie’s annual events are just the occasion you need to come by and see what we’re all about! Choose any event for the base of your trip here and stay a while.

Twelfth Night Tree Bonfire w/ crowd