Festivals near Holiday, FL.

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 ....

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. 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 ....

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 ....

St.Pete Italian Fest

• May. 16 - May 16, 2026
• Vinoy Park - St. Petersburg, FL USA

• Other / General

• $1 - $10

Get ready for a day of Italian flavor and fun at St. Pete Italian Fest on May 16 at Vinoy Park! From grape stomping and a cannoli eating contest to bo ....

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 ....

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 ....

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 ....

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 ....

5th Annual Taco Fest

• May. 2 - May 2, 2026
• Seminole City Park - Seminole, FL USA

• Food / Wine / Beer

The City of Seminole Recreation Department will host its 5th Annual Taco Fest on Saturday, May 2, 2026, from 4PM- 9PM. Taco Fest will be held at Semin ....

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 ....

Wine Down Wednesdays

• Apr. 29 - Apr 29, 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 ....

St. Petersburg Renaissance Faire

• Apr. 26 - Apr 26, 2026
• 5010 81st Ave - Pinellas Park, FL USA

• Other / General

• $25 - $50

Join us for an Elizabethan celebration like no other. Marvel in the works of Shakespeare. Cheer your jousting knight on to victory, or mourn them in d ....

St. Petersburg Renaissance Faire

• Apr. 26 - Apr 26, 2026
• 5010 81st Ave - Pinellas Park, FL USA

• Other / General

• $10 - $25

Marvel in the works of Shakespeare. Cheer your jousting knight on to victory, or mourn them in defeat. Eat a giant Turkey Legg. Drink an Ale. Let your ....

“Beyond the Prism" - A Tribute to Pink Floyd

• Apr. 25 - Apr 25, 2026
• Richey Suncoast Theatre - New Port Richey, FL USA

• Music

• $25 - $50

Richey Suncoast Theatre, in partnership with Hits 106, presents “Beyond the Prism - A Tribute to Pink Floyd” for a live engagement on Saturday, April ....

St. Petersburg Renaissance Faire

• Apr. 25 - Apr 25, 2026
• 5010 81st Ave - Pinellas Park, FL USA

• Other / General

• $10 - $25

Marvel in the works of Shakespeare. Cheer your jousting knight on to victory, or mourn them in defeat. Eat a giant Turkey Legg. Drink an Ale. Let your ....

St. Petersburg Renaissance Faire

• Apr. 25 - Apr 25, 2026
• 5010 81st Ave - Pinellas Park, FL USA

• Other / General

• $25 - $50

Join us for an Elizabethan celebration like no other. Marvel in the works of Shakespeare. Cheer your jousting knight on to victory, or mourn them in d ....

Lakeland Volunteers in Medicine Annual Swan Derby

• Apr. 24 - Apr 24, 2026
• Frances Langford Promenade - Lakeland, FL USA

• Other / General

Mark your calendars and prepare to glide into a day of feathered fun! On Friday, April 24, 2026, Lakeland Volunteers in Medicine proudly presents th ....

INK MANIA FEST

• Apr. 24 - Apr 26, 2026
• 4800 US-301 - Tampa, FL USA

• $10 - $25

Ink Mania Fest is a three-day, high-energy celebration of tattoo culture, art, music, and community—uniting thousands of artists, enthusiasts, familie ....

Franklin Street Block Party: Celebrating Earth Day

• Apr. 22 - Apr 22, 2026
• Tampa Theatre - Tampa, FL USA

• Other / General

The historic auditorium may be closed for restoration, but there are still plenty of reasons to visit Tampa Theatre! On Wednesday, April 22, Tampa’s m ....

Wine Down Wednesdays

• Apr. 22 - Apr 22, 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 ....

4th Annual Soul Revival Art Festival — The Deuces

• Apr. 19 - Apr 19, 2026
• 833 22nd St S - St. Petersburg, FL USA

• Other / General

The 4th Annual Soul Revival Art Festival returns to the historic Deuces corridor in St. Petersburg, FL for a free afternoon of live music, hands-on ar ....