Festivals near Brooksville, FL.

Mother's Day Brunch at Hotel Flor

• May. 10 - May 10, 2026
• Hotel Flor - Tampa, FL USA

• Food / Wine / Beer

Hotel Flor, downtown Tampa's historic landmark hotel, and its signature restaurant, The Dan, invite guests to celebrate the mothers in their lives wit ....

Wine Down Wednesdays

• May. 13 - May 13, 2026
• Aspirations Winery - Clearwater, FL USA

• Food / Wine / Beer

• $10 - $25

The Ultimate Mid-Week Indulgence Looking to break up the work week? Join us at Aspirations Winery for Wine Down Wednesday—an evening designed for wine ....

Downtown’s Backyard Market

• May. 14 - May 14, 2026
• 200 N Franklin St - Tampa, FL USA

Find fresh finds and city vibes at Downtown’s Backyard Market! This monthly market invites you to Tampa City Center’s Esplanade (Poe Plaza) to get dow ....

Kids Market at Yuengling Brewery Family Day

• May. 17 - May 17, 2026
• Yuengling Draft Haus \u0026 Kitchen - Tampa, FL USA

Join us for an exciting and family-friendly Kids Market during Yuengling Family Day at Yuengling Brewery! This unique event features young entreprene ....

Wine Down Wednesdays

• May. 20 - May 20, 2026
• Aspirations Winery - Clearwater, FL USA

• Food / Wine / Beer

• $10 - $25

The Ultimate Mid-Week Indulgence Looking to break up the work week? Join us at Aspirations Winery for Wine Down Wednesday—an evening designed for wine ....

FAME: The Ultimate DAVID BOWIE Tribute

• May. 23 - May 23, 2026
• Richey Suncoast Theatre - New Port Richey, FL USA

• Music

• $25 - $50

NEW PORT RICHEY, FL – March 17, 2026 – On Saturday, May 23, 2026, the historic Richey Suncoast Theatre will host a legendary musical odyssey as it pro ....

Wine Down Wednesdays

• May. 27 - May 27, 2026
• Aspirations Winery - Clearwater, FL USA

• Food / Wine / Beer

• $10 - $25

The Ultimate Mid-Week Indulgence Looking to break up the work week? Join us at Aspirations Winery for Wine Down Wednesday—an evening designed for wine ....

Lakeland PokeKon Fest SATURDAY MAY 30, 2026 | 10:00AM - 5:00PM RP FUNDING CENTER

• May. 30 - May 30, 2026
• RP FUNDING CENTER - Lakeland, FL USA

• Other / General

• $10 - $25

PokeKon-Fest - Lakeland All Pokemon Show Saturday May 30, 2026 - RP Funding Center 10:00am - 5:00pm PokeKon is the Pokemon collectors’ Mecca 1 day tr ....

Mayor’s Food Truck Fiesta

• Jun. 3 - Jun 3, 2026
• Lykes Gaslight Square Park - Tampa, FL USA

Let’s fiesta! Back by popular demand (and hunger), the Mayor’s Food Truck Fiesta is rolling in to Lykes Gaslight Park the first Wednesday of every mon ....

Downtown’s Backyard Market

• Jun. 11 - Jun 11, 2026
• 200 N Franklin St - Tampa, FL USA

Find fresh finds and city vibes at Downtown’s Backyard Market! This monthly market invites you to Tampa City Center’s Esplanade (Poe Plaza) to get dow ....

2026 Night Nation Run - Tampa, FL

• Jun. 27 - Jun 27, 2026
• Raymond James Stadium - Tampa, FL USA

• $25 - $50
• $50 - $100

Use coupon code SHINE to save on tickets! The Night Nation Run is the World’s first Running Music Festival! An ultimate blend of a Music Festival and ....

Downtown’s Backyard Market

• Jul. 9 - Jul 9, 2026
• 200 N Franklin St - Tampa, FL USA

Find fresh finds and city vibes at Downtown’s Backyard Market! This monthly market invites you to Tampa City Center’s Esplanade (Poe Plaza) to get dow ....

Downtown’s Backyard Market

• Aug. 13 - Aug 13, 2026
• 200 N Franklin St - Tampa, FL USA

Find fresh finds and city vibes at Downtown’s Backyard Market! This monthly market invites you to Tampa City Center’s Esplanade (Poe Plaza) to get dow ....

Florida Kids and Family Expo

• Aug. 22 - Aug 23, 2026
• Orange County Convention Center - Orlando, FL USA

• Other / General

• $1 - $10

The Florida Kids & Family Expo is the nation’s largest kids and family event, featuring 200+ exhibitors and two full days of nonstop fun for families. ....

Downtown’s Backyard Market

• Sep. 10 - Sep 10, 2026
• 200 N Franklin St - Tampa, FL USA

Find fresh finds and city vibes at Downtown’s Backyard Market! This monthly market invites you to Tampa City Center’s Esplanade (Poe Plaza) to get dow ....

Taste the Tradition: National Coffee Day 2025 x Cafely

• Sep. 29 - Sep 29, 2026
• 263 W Central Ave - Winter Haven, FL USA

• Nightlife

• FREE!!

Hey there, coffee lover! Get ready to raise your mug because National Coffee Day is coming up on September 29, and it’s the perfect time to celebrate ....

Celebrate a Brew-tiful National Coffee Day with Cafely

• Sep. 29 - Sep 29, 2026
• Cafely - Mount Dora, FL USA

• Nightlife

• FREE!!

As the aroma of freshly brewed coffee wafts through the air, National Coffee Day on September 29 invites everyone to raise a mug to one of the world’s ....

Downtown’s Backyard Market

• Oct. 8 - Oct 8, 2026
• 200 N Franklin St - Tampa, FL USA

Find fresh finds and city vibes at Downtown’s Backyard Market! This monthly market invites you to Tampa City Center’s Esplanade (Poe Plaza) to get dow ....

Downtown’s Backyard Market

• Nov. 12 - Nov 12, 2026
• 200 N Franklin St - Tampa, FL USA

Find fresh finds and city vibes at Downtown’s Backyard Market! This monthly market invites you to Tampa City Center’s Esplanade (Poe Plaza) to get dow ....

Downtown’s Backyard Market

• Dec. 10 - Dec 10, 2026
• 200 N Franklin St - Tampa, FL USA

Find fresh finds and city vibes at Downtown’s Backyard Market! This monthly market invites you to Tampa City Center’s Esplanade (Poe Plaza) to get dow ....

Sheryl’s BreastFest – 11th Annual Music Festival and Cancer Benefit

• May. 9 - May 9, 2026
• Lakeland Elks Lodge #1291 - Lakeland, FL USA

• Music

Sheryl’s BreastFest – 11th Annual Music Festival and Cancer Benefit is a free, family-friendly community event bringing people together through live m ....

Tampa Bay Screams Horror Convention

• May. 8 - May 9, 2026
• Holiday Inn St. Petersburg N- Clearwater by IHG - Clearwater, FL USA

• Other / General

• $25 - $50

Tampa Bay Screams is the ULTIMATE HORROR+CULT MOVIE CONVENTION, now in our 10th year! ....

Wine Down Wednesdays

• May. 6 - May 6, 2026
• Aspirations Winery - Clearwater, FL USA

• Food / Wine / Beer

• $10 - $25

The Ultimate Mid-Week Indulgence Looking to break up the work week? Join us at Aspirations Winery for Wine Down Wednesday—an evening designed for wine ....

Mayor’s Food Truck Fiesta

• May. 6 - May 6, 2026
• Lykes Gaslight Square Park - Tampa, FL USA

Let’s fiesta! Back by popular demand (and hunger), the Mayor’s Food Truck Fiesta is rolling in to Lykes Gaslight Park the first Wednesday of every mon ....

Sunflower Festival at HarvestMoon Fun Farm

• May. 2 - May 25, 2026
• HarvestMoon Fun Farm - Masaryktown, FL USA

• $10 - $25

Embrace the beauty of nature as you wander through vibrant fields of sunflowers, providing the perfect backdrop for a day filled with joy and adventur ....