EVENTS – May 2021

Due to the uncertainty of these times adjustments may be made.

Social distancing and face masks will be required during public events at this time.


Through Sunday, May 23 – Bay Area Renaissance Festival

10 am – 5 pm Saturday and Sundays. RELOCATED to Withlacoochee River Park, 12449 Withlacoochee Blvd., Dade City 33525. Come revel with the villagers of Fittleworth, a magical place of royalty, fairies and fauns. Enjoy jousting, magicians, artisans and fabulous food fit for a King, or Queen. PRESALE ticket discount ends 4/12. *** Patrons with 2020 tickets can exchange at gate.


Wednesday, May 5 Cinco de Mayo Day


Friday, May 7 – First Friday Art Walk

5 – 9 pm. Beach Blvd., Gulfport. Stroll the streets in this quaint seaside city and enjoy the wares of craftsman, artists and entrepreneurs. The galleries, boutiques and shops are open with ample dining options along the way.


Friday, May 7 – Second Anniversary Celebration – Brenda McMahon Gallery

5 – 9 pm. Brenda McMahon Gallery, 2901 Beach Blvd., Gulfport. The gallery will be celebrating it’s anniversary of highlighting the emerging local and regional artists in an array of mediums. Enjoy an evening of art and entertainment with the music of Gail Trippsmith & Company.


Friday, May 7 – Spring Concert Series – The Spazmatics

7 – 9 pm. $5 ticket is good for up to 6 people. Walk up tickets for $2 per person. Space provided is about 10 x 10 for your group. Horan Park, 7701 Boca Ciega Dr., St. Pete Beach. Enjoy an evening of live music along the waterfront in a safe and socially distant event.


Saturday, May 8 – Party Under the Lights

4 – 10 pm. Free. Historic 8th Avenue, Pass A Grille. Party in the streets with steel drums, arts & craft vendors, food and dancing in the streets to the music of the Legendary Impacs starting at 8pm.


Sunday, May 9 – HAPPY MOTHER’S DAY


Thursday, May 13 – Sailing for a Purpose

5 pm – Dockside Experience $35; Sunset Sail Excursion $75. Dolphin Landings Charter Boat Center, 4737 Gulf Blvd., St. Pete Beach. Enjoy an evening for a dockside wine and cheese event including entertainment, extend the evening with a sunset sail aboard the beautiful 51′ sailing yacht “Magic”. All proceeds to benefit the Soothe Our Souls charity which provides the serenity of the sea for those facing serious health challenges. Tickets are limited. Call 727.360.7411 for tickets and reservations.


Friday, May 14 – City of Treasure Island Liquidation Sale

8 am – 1 pm. Open to the public. Allied Building (New City Hall location ) 10451 Gulf Blvd. Treasure Island. The city will be selling excess office equipment primarily chairs, desks and shelving. The sale will be indoors and outdoors. Masks are required in order to enter the building. Parking meters will be waived for event. For more information please email or call 727-547-4575 x241.


Saturday, May 15 – Indie Faire

5 – 9 pm. Beach Blvd., Gulfport. Indie Faire features high quality local art and contemporary crafts from across a wide range of mediums, as well as jewelry and locally sourced botanicals in an outdoor and socially distanced manner along scenic Beach Boulevard in downtown Gulfport.


Friday, May 21 – Welcome Back Porch Party

7 – 9 pm. Free. Gulfport Historical Society, 5301 28th Ave. S, Gulfport. Come celebrate the reopening of the Historical Society with an evening of family fun with lawn games, crafts, live music and food. Come and see what’s planned for the year ahead.


Saturday, May 22 – Mad Beach ThrownDown Car Show and Music Fest

1 pm Car Show, 6 pm Concert. Car show registration $10 viewing is free, Concert $10 with limited tickets. ROC Park, Madeira Beach. Enjoy an afternoon of vintage cars and stay for the evening concert. The concert will feature local favorite The Pirate Flag Band as headliners with The Doug Smith Band opening the show. Proceeds will benefit local Veterans charities.


Friday, May 28 – Follow the Rainbow – The Gulfport Pride Challenge

6 – 9 pm. Registration is free. Throughout Gulfport’s downtown and waterfront. If a scavenger hunt and a Pub Crawl were to collide this would be it. Visit local businesses and complete challenges to see which team is the funniest and the fastest. For more info and to register visit


Saturday, May 29 – Gulfport PRIDE

4 – 9 pm. Proceeds to benefit the LGBTQ Resource Center, Gulfport Library, 5501 28th Ave. S, Gulfport. There will be a flag raising ceremony at 4 pm at the library to kick off the event during which there will be an ArtOut reception, vendor showcase along Beach Blvd., vibrator races and Drag by the Bay. Events will take place in various location throughout the Gulfport shopping district. The library can be found at the north end of Beach Blvd. For info visit


Monday, May 31 – Memorial Day – A time to honor those who sacrificed for our freedoms.


The month of June will be celebrating St. Pete Pride Fest throughout the month with themed weekends including the parade and street fair with fireworks. For complete details visit






Tuesdays –

Gulfport Fresh Market, Beach Blvd., Gulfport. 9 am – 2 pm. Fresh produce, culinary, plants and so much more. OPEN YEAR ROUND

Open Mike Night at Coconuts Comedy Club, 5501 Gulf Blvd., St. Pete Beach – 8 pm. 727.360.JOKE (5653)


Madeira Beach Morning Market, NEW LOCATION -15000 Madeira Way. 10 am – 2 pm.

A Taste of Art – Brenda McMahon Gallery, 2901 Beach Blvd., Gulfport. Weekly hands on art experiences.


Wednesday through Saturday – National comics at Coconuts Comedy Club

4/28 – 5/01 – J.F. Harris 5/05 – 5//08 – Helen Keaney

5/12 – 5/15 – Quevaughn Bryant 5/19 – 5/22 – Mark James

5/26 – 5/29 – Leslie Norris

Celebrating their 35th Anniversary this month!


Friday Morning Market – Treasure Island Community Center, 1 Park Pl. 9 am – 2 pm. CLOSED NOW UNTIL DECEMBER 2021

First Friday – Gulfport’s Artwalk – Juried by their peers local artists offer their unique style throughout various mediums. Live entertainment with shops and restaurants open. 5 – 9 pm.

3rd Saturday – Gulfport’s Indie Faire – The streets are lined with local artists, unique trinkets, live entertainment with shops and restaurants open. 5 – 9 pm.


Indian Shores Sunday Market – 9 am – 1 pm. Indian Shores Municipal Bldg. 19305 Gulf Blvd. Indian Shores MAY 16 – Last Market as End of Season until November

Corey Ave. Sunday Market – 10 am – 2 pm. Over 75 vendors. Corey Avenue, St. Pete Beach.

Will run through May and return in October

First Sunday – Soothe Our Souls, a cost free respite upon the sea for those facing serious health challenges and their support group. For more details visit or call 727.360.7411 which will be the dock office of Dolphin Landings Charter Boat Center




CDC has updated the guidance that adults who have been fully vaccinated may attend outdoor functions unmasked. 

Please respect the guidelines of event organizers.

Let’s keep us all safe to Play another day!



Wishing you a wonderful month ahead filled with memory making moments ~