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Search filters: Events in Florida.

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First Sat -Cruisin' Dearborn Market & Car Show - May
May 2, 2026

First Sat -Cruisin' Dearborn Market & Car Show - May

Whimsey Boutique at the Sea Star Cove, Englewood, FL

Status: Updated 9/11/2025

  • # of Exhibitors: 30
  • Juried: no
  • Prize Money:
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ReptiDay Port Charlotte
May 2, 2026

ReptiDay Port Charlotte

Charlotte County Fairgrounds, Port Charlotte, FL

Status: Updated 3/29/2026

  • # of Exhibitors: 75
  • Juried: no
  • Prize Money: na
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Jamming at the Settlement - May
May 2, 2026

Jamming at the Settlement - May

Pioneer Settlement for the Creative Arts, Pierson, FL

Status: Updated 3/29/2026

There will be 6 stages with Regional and Local talent. The entertainment will be Bluegrass, Country, Folk, Gospel, Old-time and Ragtime.
  • # of Exhibitors: 16
  • Juried: no
  • Prize Money: na
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Wildflower Festival & Plant Sale
May 2, 2026

Wildflower Festival & Plant Sale

Heritage Park & Gardens, Live Oak, FL

Status: Updated 3/25/2026

There will be 2 stages with Regional and Local talent. The entertainment will be Alternative, Americana, Bluegrass, Blues, Children's, Christian, Country, Folk, Jam, Jazz, Rap/Hip-hop, R & B/Soul, Rock and Roots, and there will be other activities like chalk art, movie night.
  • # of Exhibitors: 75
  • Juried: no
  • Prize Money:
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Florida Wiener Dog Derby XVI With Riverfest -Sweet 16-
May 2, 2026

Florida Wiener Dog Derby XVI With Riverfest -Sweet 16-

Curtis Hixon Park, Tampa, FL

Status: Updated 9/9/2025

  • # of Exhibitors: 5
  • Juried: no
  • Prize Money: na
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Pinellas Pepper Fest
May 2 - 3, 2026

Pinellas Pepper Fest

England Brothers Band Shell Park, Pinellas Park, FL

Status: Updated 12/31/2025

There will be 1 stage with Local talent. The entertainment will be Alternative, Bluegrass, Blues, Country, Rock and Variety, and there will be other activities like pepper eating contest / favorite vendor / lolly lick-a-thon.
  • # of Exhibitors: 150
  • Juried: no
  • Prize Money: na
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52nd Annual Art in the Park
May 2 - 3, 2026

52nd Annual Art in the Park

Rockefeller Gardens/The Casements, Ormond Beach, FL

Status: Updated 2/24/2026

There will be 2 stages with Regional and Local talent. The entertainment will be Beach, Blues, Country, R & B/Soul, Rock, Top Forty/Pop and Variety, and there will be other activities like kids' craft zone, art exhibit, interactive art.
  • # of Exhibitors: 100
  • Juried: no
  • Prize Money: $3,500
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Fort Myers Blueberry Fest
May 2 - 3, 2026

Fort Myers Blueberry Fest

Lee Civic Center, North Fort Myers, FL

Web: FtMyersFest.com

Status: Updated 10/22/2025

  • # of Exhibitors: 200
  • Juried: yes
  • Prize Money:
(386) 860-0092
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ArtsQuest Fine Arts Festival
May 2 - 3, 2026

ArtsQuest Fine Arts Festival

Grand Boulevard's Town Center, Miramar Beach, FL

Status: Updated 9/10/2025

There will be 1 stage with Regional and Local talent. The entertainment will be Beach, Bluegrass, Blues, Children's, Classical/Symphony, Folk, Funk, Jazz, Rockabilly, Roots, Swing and World.
  • # of Exhibitors: 150+
  • Juried: yes
  • Prize Money: $10,000
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Intergalactic Bead Show-Pompano, FL
May 2 - 3, 2026

Intergalactic Bead Show-Pompano, FL

E Pat Larkins Community Center, Pompano Beach, FL

Status: Updated 3/10/2026

  • # of Exhibitors: 80
  • Juried: no
  • Prize Money: na
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Downtown Sarasota Spring Craft Fair
May 2 - 3, 2026

Downtown Sarasota Spring Craft Fair

5 Points Park, Sarasota, FL

Status: Updated 1/15/2026

  • # of Exhibitors: 100
  • Juried: yes
  • Prize Money: na
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Waldo Farmers & Flea Market - May
May 2 - 31, 2026

Waldo Farmers & Flea Market - May

Waldo Farmers & Flea Market, Waldo, FL

Status: Updated 1/12/2026

  • # of Exhibitors: 800
  • Juried: no
  • Prize Money: na
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Star Wars Day
May 2026 (dates not updated)

Star Wars Day

Bo Diddley Plaza, Gainesville, FL

Status: Updated 2/24/2025

There will be 1 stage with Local talent. The entertainment will be Children's, and there will be other activities like kid's dance party, light saber duels, costume contest, screening of empire strikes back.
  • # of Exhibitors: na
  • Juried: no
  • Prize Money:
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Arches Cinco de Mayo
May 2026 (dates not updated)

Arches Cinco de Mayo

Erickson & Jenson Seafood, Fort Myers Beach, FL

Status: Updated 7/9/2024

There will be 1 stage with International talent. The entertainment will be Country, Ethnic, Latin and Rock, and there will be other activities like raffles, mexican games, low rider car show.
  • # of Exhibitors: 21
  • Juried: no
  • Prize Money:
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Havanareggaefest
May 2026 (dates not updated)

Havanareggaefest

5F Farm Event Center, Quincy, FL

Status: Updated 4/1/2025

There will be 1 stage with International, National, Regional and Local talent. The entertainment will be Reggae.
  • # of Exhibitors: Tbd
  • Juried: no
  • Prize Money: na
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Festivals of Speed Ocala
May 2026 (dates not updated)

Festivals of Speed Ocala

World Equestrian Center, Ocala, FL

Status: Updated 2/10/2025

There will be 1 stage with Local talent. The entertainment will be Jazz and Swing, and there will be other activities like car display.
  • # of Exhibitors: tba
  • Juried: no
  • Prize Money: na
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South Florida Home Show
May 2026 (dates not updated)

South Florida Home Show

Charles F. Dodge City Center, Pembroke Pines, FL

Status: Updated 2/10/2025

  • # of Exhibitors: tba
  • Juried: no
  • Prize Money: na
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Winter Haven Summer Farmers Market - May
May 2026 (dates not updated)

Winter Haven Summer Farmers Market - May

BB&T Bank Parking Lot, Winter Haven, FL

Status: Updated 2/20/2025

There will be 1 stage with Regional and Local talent. The entertainment will be .
  • # of Exhibitors: 40+
  • Juried: no
  • Prize Money: na
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Orange Park Farmers and Arts Market - May
May 2026 (dates not updated)

Orange Park Farmers and Arts Market - May

Town Hall Park, Orange Park, FL

Status: Updated 2/20/2025

There will be 1 stage with Regional and Local talent. The entertainment will be .
  • # of Exhibitors: 100+
  • Juried: yes
  • Prize Money: na
4.29/5
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Truman Waterfront Market - May
May 6 - 28, 2026

Truman Waterfront Market - May

Truman Waterfront Park, Key West, FL

Status: Updated 3/21/2026

  • # of Exhibitors: 60
  • Juried: no
  • Prize Money: na
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Country Thunder Florida
May 8 - 10, 2026

Country Thunder Florida

Raymond James Stadium, Tampa, FL

Status: Updated 11/17/2025

There will be 3 stages with International, National, Regional and Local talent. The entertainment will be Americana, Bluegrass, Country, DJ/Dance/Techno and Folk, and there will be other activities like demonstrations, contests, saloons w/dancing.
  • # of Exhibitors: 50
  • Juried: no
  • Prize Money: na
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Saturday @ Zephyr Park - May
May 9, 2026

Saturday @ Zephyr Park - May

Zephyr Park, Zephyrhills, FL

Status: Updated 3/9/2026

  • # of Exhibitors: 60
  • Juried: no
  • Prize Money:
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Mother's Day Craft Fair
May 9, 2026

Mother's Day Craft Fair

West Florida High School Football Stadium, Pensacola, FL

Status: Updated 3/3/2026

  • # of Exhibitors: 20+
  • Juried: no
  • Prize Money:
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Funk Fest - Jacksonville
May 2026 (dates not updated)

Funk Fest - Jacksonville

Metropolitan Park, Jacksonville, FL

Status: Updated 5/2/2025

There will be 1 stage with National and Regional talent. The entertainment will be Ethnic, Funk, Rap/Hip-hop, R & B/Soul, Rock and Top Forty/Pop.
  • # of Exhibitors: tba
  • Juried: no
  • Prize Money: na
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