Welcome to your ultimate guide to May events in Northeast Florida! From historic reenactments and waterfront cruises in St. Augustine to family-friendly festivals and outdoor adventures throughout Clay, Putnam, and Flagler counties, there’s something for everyone this month. Whether you’re searching for free kids’ activities, live music under the stars, or unique cultural experiences, our curated lineup of 28 May events has you covered. Bookmark this page and never miss a Spring festival, museum open house, or outdoor nature walk happening right in your backyard!
Historical & Cultural
Duel on Aviles Street
Location: Aviles Street between King & Cathedral Streets, St. Augustine, FL
Date & Time: Sat–Sun, May 3–4, 2025 • various reenactment times
Cost: Free
Summary: Costumed interpreters stage an authentic 19th-century pistol duel, with period music and commentary on America’s oldest street.
More Info: https://www.staugustinehistoryfestival.com/event/duel-on-aviles-street/Celebrating the History of St. Augustine’s Spanish Colonial Quarter
Location: 33 St. Francis St., St. Augustine, FL
Date & Time: May 1–31, 2025 • 10 AM–5 PM daily
Cost: Free (special guided tours $5/person)
Summary: Self-guided tours and live demos reveal 450+ years of Spanish Florida in restored buildings, with costumed guides sharing personal stories.
More Info: https://www.floridashistoriccoast.com/events/celebrating-the-history-of-st-augustines-spanish-colonial-quarter-one-house-at-a-time/
Arts & Culture
Flo-Arts Students Celebrate Musicals
Location: Center for Spiritual Living, 1795 Old Moultrie Rd., St. Augustine, FL 32084
Date & Time: Sat, May 10, 2025 • 4 PM–5 PM
Cost: Free
Summary: Local youth perform highlights from beloved musicals in this family-friendly showcase.
More Info: https://www.romanzafestivale.com/event/floarts/Chamber Music Series: David Pedraza, Violist
Location: Grace United Methodist Church, 8 Carrera St., St. Augustine, FL 32084
Date & Time: Wed, May 14, 2025 • 12 PM–1 PM
Cost: Free
Summary: A lunchtime recital featuring Baroque to contemporary works by noted violist David Pedraza.
More Info: https://www.romanzafestivale.com/event/david-pedraza/Psychic Medium Travis Holp at Café Eleven
Location: The Original Cafe Eleven, 501 A1A Beach Blvd., St. Augustine Beach, FL 32080
Date & Time: Sat, May 31, 2025 • 8 PM–10 PM
Cost: VIP $35 / GA $25 advance (day-of higher)
Summary: An intimate evening of mediumship, live music, and messages from loved ones with Travis Holp.
More Info: https://www.floridashistoriccoast.com/events/physic-medium-travis-holp-at-cafe-eleven/
Tours & Cruises
Mother’s Day Sail Aboard Schooner Freedom
Location: St. Augustine Municipal Marina, 111 Avenida Menendez, St. Augustine, FL 32084
Date & Time: Sun, May 11, 2025 • 1:15 PM (day sail) & 6:15 PM (sunset sail)
Cost: $45 (day) / $65 (sunset)
Summary: Treat Mom to a relaxing day or sunset cruise aboard this historic 76-ft schooner, complete with narration and light snacks.
More Info: https://www.floridashistoriccoast.com/events/mothers-day-sail-aboard-schooner-freedom/Red Boat Tours Mother’s Day Special
Location: Vilano Pier, 260 Vilano Rd., St. Augustine, FL 32084
Date & Time: Sun, May 11, 2025 • 12 PM (dolphin tour) & 6:30 PM (BYOB sunset)
Cost: $29 (dolphin) / $39 (sunset)
Summary: Choose a noon dolphin-spotting cruise or a BYOB sunset tour—both include wildlife commentary and scenic views.
More Info: https://www.floridashistoriccoast.com/events/red-boat-tours-mothers-day-special/St. Augustine Sailing Sunset Tasting Cruise
Location: 3076 Harbor Dr., St. Augustine, FL 32084
Date & Time: Fri–Sun in May • 6:30 PM–8:30 PM
Cost: $299 pp
Summary: Multi-course tasting menu paired with wine or cocktails aboard a yacht at golden hour over the water.
More Info: https://www.floridashistoriccoast.com/events/st-augustine-sailing-sunset-tasting-cruise-2/
Music & Concerts
Given to Fly: The Pearl Jam Experience
Location: The Original Cafe Eleven, 501 A1A Beach Blvd., St. Augustine Beach, FL 32080
Date & Time: Sat, May 24, 2025 • 8 PM–10 PM
Cost: $20–$35
Summary: Outdoor, high-energy Pearl Jam tribute show just steps from the beach.
More Info: https://www.floridashistoriccoast.com/events/given-to-fly-the-pearl-jam-experience-at-cafe-eleven/Rick Springfield Live
Location: The AMP at St. Augustine, 54 Sevilla St., St. Augustine, FL 32084
Date & Time: Fri, May 16, 2025 • 8 PM
Cost: See site for tickets & VIP packages
Summary: Hear “Jessie’s Girl” and more from the ’80s rock icon.
More Info: https://www.theamp.com/events/detail/rick-springfieldAs If the ’90s Fest
Location: Downtown St. Augustine (venue TBA)
Date & Time: Sat, May 17, 2025 • all day
Cost: See site for details
Summary: A nostalgic block-party celebrating ’90s music, pop culture, fashion, and more.
More Info: https://www.asifthe90sfest.com/
Festivals & Fairs
Palatka Blue Crab Festival
Location: Riverfront Plaza, 1 S. 2nd St., Palatka, FL 32177
Date & Time: Sat–Sun, May 3–4, 2025 • 10 AM–10 PM
Cost: Free admission; food & activities extra
Summary: Seafood feast on the riverfront with live music, arts & crafts, and a kids’ zone.
More Info: https://www.palatkabluecrabfestival.com/Clay County Barkfest
Location: Clay County Fairgrounds, 2463 State Road 16, Green Cove Springs, FL 32043
Date & Time: Sat, May 17, 2025 • 10 AM–2 PM
Cost: Free
Summary: Dog-centric expo featuring contests, adoptions, vendors, bounce houses, and live music.
More Info: https://www.bringfido.com/event/53925
Family & Kids Activities
FREE Kids’ Fishing Clinic
Location: Herschel King Park, 7334 Sunrise Blvd., Keystone Heights, FL 32656
Date & Time: Sat, May 10, 2025 • 9 AM–12 PM
Cost: Free (rods provided for first 150 kids)
Summary: Learn casting, knot-tying, conservation, and water safety in this hands-on clinic.
More Info: https://www.visitflagler.com/event/free-kids-fishing-clinic/22164/Bark in the Park
Location: Sunrise Park Dog Park, 7334 Sunrise Blvd., Keystone Heights, FL 32656
Date & Time: Sat, May 10, 2025 • 10 AM–2 PM
Cost: Free
Summary: Pet-friendly fair with food trucks, vendor booths, contests, and family fun.
More Info: https://exploreclay.com/event/bark-in-the-park/Railroad Open House
Location: David Browning Railroad Museum, 222 N 11th St., Palatka, FL 32177
Date & Time: Sat, May 10, 2025 • 10 AM–2 PM
Cost: Free
Summary: Explore Palatka’s rail history, watch scale-model trains in action, and tour historic exhibits.
More Info: https://www.facebook.com/events/1600881690604426
Sports & Fitness
Game On Ponte Vedra Triathlon (Spring)
Location: Sawgrass Village, Ponte Vedra Beach, FL
Date & Time: Sun, May 4, 2025 • 7 AM start
Cost: Registration tiers vary
Summary: Sprint & Olympic-distance triathlon with open-water swim, bike, and run on scenic coastal courses.
More Info: https://runsignup.com/Race/FL/PonteVedraBeach/GameOnPonteVedraTriathlonSpringLine Dancing at The VIA
Location: VIA at Green Cove Springs, 1300 Citizens Way, Green Cove Springs, FL 32043
Date & Time: Fri, May 9, 2025 • 6 PM–8 PM (1st & 3rd Fridays)
Cost: Donation-based
Summary: Social line-dance class—no partner needed; all levels welcome.
More Info: https://exploreclay.com/event/line-dancing-at-the-via/Bike Rodeo
Location: Clay County Fairgrounds, 2463 State Road 16, Green Cove Springs, FL 32043
Date & Time: Sat, May 10, 2025 • 9 AM–12 PM
Cost: Free
Summary: Helmet fittings, obstacle-course skills, traffic drills, and safety demos led by law enforcement and volunteers.
More Info: https://exploreclay.com/event/bike-rodeo/
Charity & Fundraisers
13th Annual Fort Mose Golf Tournament
Location: St. Johns Golf Club, 4900 Cypress Links Blvd., Elkton, FL 32033
Date & Time: Fri, May 16, 2025 • 12 PM check-in / 1 PM shotgun
Cost: $125 early bird / $140 after May 9
Summary: Best-ball fundraiser for the Fort Mose Historical Society, complete with musket salute and awards.
More Info: https://fortmose.org/fort-mose-annual-golf-tournament-2022/Catholic Charities St. Johns County Charity Golf Tournament
Location: The Palencia Club, 600 Palencia Club Dr., St. Augustine, FL 32095
Date & Time: Mon, May 19, 2025 • 7:30 AM registration / 9 AM shotgun
Cost: $150/player
Summary: Support local food and financial assistance programs with this 5th annual scramble-style tournament.
More Info: https://one.bidpal.net/ccbpalenciagolf/welcome2025 Wolfson Children’s Bass Tournament
Location: TBA (see site)
Date & Time: Sat, May 24, 2025 • time TBA
Cost: Registration & fees on site
Summary: Youth fishing tournament benefiting Wolfson Children’s Hospital, prizes and fun for all skill levels.
More Info: https://giving.baptistjax.com/event/2025-wolfson-childrens-bass-tournament/e581823
Car & Vehicle Shows
15th Annual Rev It Up! Car Show
Location: Moosehaven, 1701 Park Ave., Orange Park, FL 32073
Date & Time: Sat, May 10, 2025 • 10 AM–2 PM
Cost: Free
Summary: Classic cars, food trucks, DJ tunes, raffles, and scholarships at this family-friendly show.
More Info: https://exploreclay.com/event/15th-annual-rev-it-up-car-show/
Markets & Expos
Boardwalk Bazaar at Marina Munch
Location: 111 Avenida Menendez, St. Augustine, FL 32084
Date & Time: Sat, May 17, 2025 • 10 AM–3 PM
Cost: Free
Summary: Waterfront artisan market with local makers, food trucks, live acoustic music, and scenic river views.
More Info: https://www.floridashistoriccoast.com/events/boardwalk-bazaar-at-marina-munch/American Farmstead Convention 2025
Location: Clay County Fairgrounds, 2463 State Road 16, Green Cove Springs, FL 32043
Date & Time: Sat–Sun, May 31–Jun 1, 2025 • times vary
Cost: Registration fees vary (see site)
Summary: Workshops, demos, and a farmers’ market focused on homesteading skills and sustainable living.
More Info: https://exploreclay.com/event/american-farmstead-convention-2025/
Community & Safety
Pool Safety Day
Location: Palm Coast Aquatics Center, 339 Parkview Dr., Palm Coast, FL 32137
Date & Time: Sat, May 24, 2025 • 1 PM–4 PM
Cost: Free
Summary: Water-safety demos, mini swim lessons, first-aid basics, and pool games for all ages.
More Info: https://www.palmcoast.gov/events/home/details/pool-safety
Outdoor & Nature
Guided Bird Walk: Anastasia
Location: Anastasia State Park, 300 Anastasia Park Rd., St. Augustine, FL 32080
Date & Time: Sat, May 17, 2025 • 8 AM–10 AM
Cost: Free (park entry applies)
Summary: Ranger-led walk teaching local bird identification and ecology in a coastal hammock habitat.
More Info: https://www.floridashistoriccoast.com/events/guided-bird-walk-anastasia/Night Under the Stars
Location: St. Johns County Fairgrounds, 2910 County Road 16, Hastings, FL 32145
Date & Time: Fri, May 23, 2025 • 8 PM–11 PM
Cost: $10/adult • $5/kids
Summary: Telescope stations, astronomy talks, and family activities beneath the Milky Way.
More Info: https://www.floridashistoriccoast.com/events/night-under-the-stars-at-st-johns-county-fairgrounds/
Don’t let May slip by without experiencing the best that Northeast Florida has to offer. Plan ahead for our Mother’s Day sails, Blue Crab Festival, and one-of-a-kind ’90s block party, or discover hidden gems like the Railroad Open House and Boardwalk Bazaar. With free and ticketed options to suit every budget, these events are the perfect way to connect with your community—and stay in the know on St. Augustine events, family outings, and local fundraisers. Keep this guide handy, share it with friends, and get ready to make May your most memorable month yet!
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