In this modern age of cancel culture, it’s nice to know there’s still a place where a wench can be a wench and a scallywag can be a scallywag.
In truth, the Hudson Valley Pirate Festival is (mostly) a far more family-friendly spin on the dark historic nature of pirate culture. Probably for the better – we’d like to hang on to our doubloons and avoid scurvy.
The event started from humble beginnings just three years ago, but it quickly grew into a big to-do featuring scores of costumed performers and many more attendees. It almost immediately graduated from its Cantine Field port of call to the Ulster County Fairgrounds in New Paltz. This year’s festivities will last all this weekend, May 13-14, running 11am-6pm.
If you’ve ever been to a Renaissance faire, this get-together is a little like that, but with considerably more white-and-black pinstripes. There will be singing, dancing, games of skill, sword fighting, and silly accents. Over 75 vendors are slated to participate, with many ren faire-like wares such as period clothing, crystals, jewelry, art and crafts.
Food and beverage vendors range from standard festival fare like chicken tenders, hot dogs and burgers to hand-crafted sodas, Mexican cuisine and lemonade made from homemade syrups. MkKrakynn’s Pub will be slinging alcoholic beverages (including ancient classics like grogg and hetta) and Springbrook Hollow Farm Distillery will be on hand for liquor tastings.
A separate children’s area delights in the lighter side of pirate culture, with appearances by a menu of mythic creatures including mermaids, unicorns and fairy folk. Wherever you go, expect lots of interactive fun with many fantastical characters as you roam the fairgrounds.
The fast-growing fest was founded by locals Cheryl Olsen (“Boss Wench”) and Courtney Beck (“Boss Wench II”). Inspired by pirate movies and the classic family film Muppet Treasure Island, they enlisted a small army of volunteers and buccaneers and quickly grew the annual event into a magnet for locals and tourists alike.
Attendees are encouraged to dress as pirates, mermaids, and anything adjacent to the sea-faring life. Admission is $15 for adults and $10 for children 5-13 (under 4 is free).
For the real sea dogs who like to get squiffy, an adults-only night show will take place May 13 at 7pm ($5 admission). The night will feature bawdy performances from characters such as Pleazure, Hooters, Giggle, Sissy Swallows, Creature, Tantalizing Toni, Sassy Frassy and Cherries Jubilee. Some of what the festival says are “things you will probably see”: Banana and cherry pie eating contests, a cleavage contest with googly eyes and trampolines, and tattoo/piercing contests where participants must show off each body alteration to determine who wins with the most. There may also be rousing renditions of songs like “Knockers Up” and “Roll Me Over, Lay Me Down and Do It Again!”. Audience participation is greatly encouraged. It goes without saying that night will be an 18-and-up affair.
And contrary to everything you thought you knew about pirates, Mother’s Day is very important to them. There will be a special Mother’s Day Brunch at 2pm on May 14, free to all moms and $5 for family members. A “dashing young pirate captain” will be on hand to greet your mom with a special gift. Reservations are strongly suggested – email mystikbazaarevents@gmail.com to save your spot.
For more information or to purchase tickets online, visit hvpiratefest.20m.com.
Join the family! 
