Two Hot Festivals, One Cool Town.

This website is dedicated to supporting vendors and guests interested in the Longwood Pirate Days Festival held on the last weekend in February and the Longwood Arts and Crafts Festival held on the 3rd weekend in November. If you are interested in other events in the city of Longwood, FL visit their website

Annually in February

Longwood Pirate Days

Get ready for the 5th annual Longwood Pirate Days!

Central Florida’s coolest festival will showcase pirates, vendors, a pirate village with ship for kids to climb, a special bounce crazy kid zone, music and fabulous entertainment. A large assortment of delicious festival food options will be available along with beer, wine, and cocktails. Ample parking can be found at the hospital. This family friendly event will be held in beautiful Reiter Park. Sorry, no dogs allowed in the park. The festival is Free to attend!

Annually in November

Longwood Arts & Crafts Festival

200 Best Logo 2022

We are proud to announce that the Longwood Arts and Crafts Festivals not only ranked for the very first time in Sunshine Artists annual Top 200 Classic/Contemporary Craft Festivals in America, but made the Top 50! 

2024 marks the 48th annual Longwood Arts and Crafts Festival! This highly anticipated event will feature more than 200 artists and hand craft exhibitors selling unique items, fine jewelry and seasonal decor just in time for you to get a jump on the holiday shopping season. There will be festival food, beer, wine & music. Ample parking can be found at the hospital. The event is Free to attend. 

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