We have an amazing lineup of live music, magic, musical pirate acts, and more!

Professor Bamboozel

Bamboozle, an award-winning, full-time variety family entertainer will be bringing his Balloonery Loonery act and interactive magic and illusion show to Festival of Sail!

In the Flavor of the “Old Time Illusionary Side Show,” he brings to life the magic classics as well as the new and state-of-the-art and original magic and illusions, featuring random members right out of his audience as his assistants! During his “Grand Stage” illusion shows, parents can see their kids floating in the air, an egg hatching into a live bird in a guests hands, furniture flying off the stage over the audience’s heads, and of course slicing and dicing! Fascinating sets, age-appropriate humor and high production value make this show a “DONT MISS!”

The Professor is also a world-class, award-winning balloon twister, seldom ever stumped by a special request. He can create thousands of classic twisty balloon creations as well as many originals – all at lightning speed!

The Professor has performed in night clubs, cabarets, cruise ships, grand stage theaters, national sporting events, live network television and in The Warner Bros. blockbuster movie “Practical Magic” with Sandra Bullock & Nicole Kidman.

Be a part of the magic, see Professor Bamboozles Magic Productions and Balloonary Loonary at Festival of Sail!


PDXYar: The Swashbucklers of Stumptown

PDXYAR, also know as “The Swashbucklers of Stumptown,” will entertain festival-goers with their high-energy Pirate invasion, which includes a mix of high-seas mischief, sea shanties, and interactive nautical nonsense.

Enjoy historical and interactive presentations that teach what life was like aboard a ship during the Golden Age of Piracy.

Visit Website

Bathory's Lesset & Wicked Will

We be wandering Pirates, entertaining the crowds as we go, singing sea shanties periodically, and work the crowd to join in. Our short skits entertain lasses and lads young and old.

We love to take all manner of photos with whoever asks.
Nathan Sloan

Nathan Sloan

“Spending the majority of his childhood surrounded by jazz, funk, and classical music came to be a solid foundation for Nathan Sloan. With scores of outside influence, Nathan Sloan began creating music at age four. Never settling for just one genre, Nathan has gone back and forth between tastes, which lead up to an experimental style of independent pop that permeates his art.” – Paul Zollo (American Songwriter Magazine)

Visit Website


Crushingcrayons exemplifies the unique sound of hard-hitting rock and roll-groovy-funk jams to spread their unforgettable organic sound. A five-piece band of brothers on a mission to radiate their music, Crayons evoke childhood innocence, but what’s happening here seems more adult — intentional creative violence. A broken crayon is frustrating. But crush them up and melt them, and you have something new, colorful, unpredictable.

Visit Website

Caught Red Handed

CAUGHT RED HANDED is a popular trio based in Bandon, Oregon. They are known for their strong 3-part vocal harmony, flashy instrumental breaks, and quirky conversation. They play original tunes from their upcoming CD release “Breakin’ Out” as well as a wide variety of music from the Americana songbook. The band brings together Bob Shaffar (fiddle & dobro), Kenny Croes (acoustic guitar, u-bass & banjo) and Mike Dado (bass guitar, acoustic guitar & banjo), all accomplished singers, songwriters and multi-instrumentalists in the country, bluegrass, folk and rock traditions. They perform regularly at pubs, coffee houses, and festival events throughout Oregon.

Visit Website