It’s a delicious weekend in more ways than one! Mouthwatering food festivals abound, but that’s not all! Air shows, live concerts, a tattoo festival, even movable theater in the woods prove that there is always something fascinating to do in Tampa Bay – and you can always find it right here!
Theater Thursday
Tales by Twilight: A Midwinter Night’s Tale – Presented by American Stage
Boy Hill Nature Preserve, St. Pete
Step into a world of magic, music, and whimsy as Shakespeare’s A Midsummer Night’s Dream comes to life like never before—on the winding trails of Boyd Hill Nature Preserve. In this enchanted, walk-through experience, the line between nature and theater disappears, transporting you into a dreamscape bursting with light, color, and transformation. Follow the lovers as they stumble through the woods, encounter mischievous fairies, and become tangled in spells and mistaken identities. Watch as the forest itself becomes a character—glowing with twinkling lights, pulsing with live music, and shimmering with the energy of dreams.
With nods to Shrek-style humor and heart, and a cast of magical misfits, this playful reimagining invites audiences of all ages to rediscover the joy of nature and story. Prepare to be surprised, delighted, and maybe even transformed. This isn’t just a play. It’s an adventure. A dream you can walk through.
Now – Sunday, March 8th
Find tickets, performance times, and more information HERE.
Friday
St. Petersburg Seafood & Music Festival
Vinoy Park, DTSP Waterfront
Gather your family and friends to savor the food, music, and beautiful views of downtown St. Petersburg. In addition to the music, explore a marketplace of arts, crafts, and fine products between performances, offering a perfect opportunity to find unique treasures. Indulge in a variety of delectable foods cooked on-site, featuring the freshest ingredients from local restaurants and food purveyors. Enjoy a selection of seafood entrees and vegetarian dishes, accompanied by a variety of side dishes and scrumptious desserts. Both alcoholic and non-alcoholic drinks will be available to complement your meal.
As you feast, sit back and enjoy live musical performances by some of the most talented musicians from the local and regional circuit.
Friday – Sunday, February 20th – 22nd
Find tickets, schedules, and more information HERE.
Cigar City Tattoo Fest
The Cuban Club, Ybor City
Nowadays, great “ink” is fast becoming an essential fashion statement for many – a colorful avenue for self-expression. If you can relate or are, at a minimum, ‘pigment curious,’ then this event is definitely for you! Organizers have curated over 100 of the best tattooers from across the globe for this exclusive event. Many artists will be taking walk-up clients, so don’t be shy! With thousands of designs to choose from, there is something for everyone at this tattoo convention in Tampa. Immerse yourself in the best tattoo experience Tampa has to offer.
What to expect:
LIVE Tattooing – Hand Made Art – Food Trucks – Live Music Daily – Oddities and Vendors – Classic Cars – Full Bar – Punk Rock Flea Market – And More!
Friday – Sunday, February 20th – 22nd
Find more information HERE.
Saturday
49th Gasparilla Distance Classic
Bayshore Blvd, Tampa
Registration may be closed, but you can attend one of multiple events and cheer the runners on! The weekend will include four distances plus four challenges: the PGDC 15K, PGDC 5K, the Publix Gasparilla Half Marathon (13.1 miles), and the Publix Gasparilla 8K. Feeling up to a challenge, the weekend also includes the Michelob Ultra Challenge (15K, 5K, Half Marathon, and 8K), Michelob Ultra Pure Gold Challenge (15K and Half Marathon), Michelob Ultra Infusion Challenge (15K and 8K), and the Michelob Ultra Zero Challenge (5K and 8K).
This weekend is personal for me. I will be accompanying my brother, Bruce Reiss, as he runs his 39th consecutive Gasparilla 5k and is named a legacy participant. This year, though, the battle is not only against the course, but against stage 4 prostate cancer with metastasis. His family will be with him to walk or wheel, or whatever gets us to the finish line. Hopefully, we can raise some awareness about this disease, that if caught early, is highly treatable. Gentlemen, get yourself a PSA test today, if not sooner, and help me cheer on my big brother. Thank you.
Saturday & Sunday, February 21st & 22nd
Find events, schedules, maps, and more information HERE.
Plant City Planes, Trains & Automobiles
Plant City Airport, Plant City
Planes, Trains, and Automobiles is a beloved one-day community event featuring a wide variety of activities geared towards families each year at the Plant City Airport. Featured highlights will be numerous aircraft on display, a car show, and operating model train layouts. First responder vehicles and personnel along with train safety vehicles and equipment will also be in the lineup. There will be many hands-on stations for kids, including STEM education exhibits and flight simulators from the Aerospace Center for Excellence, Young Eagles discovery flights conducted by our local Experimental Aircraft Association chapter, Scout merit badge opportunities (TBA), a pinewood derby, and many other activities. Younger children will enjoy inflatable bounce houses and other fun adventures just for them! Food trucks and local vendor displays will also be part of the lineup where area businesses can showcase their products and services to attendees for a nominal fee.
Saturday, February 21st @10am – 3pm
Find tickets, schedules, and more information HERE.
For a Good Cause: Cupid’s Undie Run
Golden Isles Brewing Co., St. Pete
Every February, when most people are hiding from the cold, thousands run straight into it – by choice. Some wear only their underwear, others opt for tutus or full-blown costumes. It’s called Cupid’s Undie Run, a nationwide event benefiting the Children’s Tumor Foundation (CTF) that turns a winter day into a celebration of laughter, courage, and half-frozen selfies – all to speed the search for life-changing treatments.
The event funds research into NF (short for neurofibromatosis and schwannomatosis) – a group of genetic conditions that cause tumors to grow on nerves throughout the body. Since it began in 2010, Cupid’s has become a fixture on America’s Best Fun Runs lists and has raised millions for science that’s changing lives.
The day starts with music, laughter, and that “are we really doing this?” buzz before everyone takes off for a quick “mile-ish” dash – some in underwear, others in costumes, all in for the cause. Streets come alive with color and spirit as runners make the NF cause impossible to miss. Then it’s back inside for the kind of party only Cupid’s can pull off – dancing, celebrating, and a crowd that doesn’t want it to end.
Saturday, February 21st @11am – 3pm (runs starts at 1pm)
Find schedules and more information HERE.
Now on View – HCC’s One-Day-Only Public Art Festival
Multiple sites, Ybor City
Meet Tampa-based artists and enjoy four hours of music, interactive visual art and live performance reflecting on Tampa’s past, present and future.
Book Your Free Ybor City Art & History Tour – Explore Now on View 3 and Ybor city with a guided tour. Reserve a ticket for a Now on View 3 guided tour with Jorge Contreras. Each ticket is valid for one tour at 11 AM, 12 PM (tour in Spanish), or 2 PM. Each tour will visit every stop along the one-day art festival route, highlighting the artists and their work while also sharing insights into Ybor City’s history.
Saturday, February 21st @11am – 3pm
Find tickets, schedules, and more information HERE.
2026 Art & Seafood on the Waterfront
Waterfront Park, Safety Harbor
Art & Seafood on the Waterfront has quickly become the Safety Harbor Chamber’s signature event. Showcasing the area’s best seafood, a Celebrity Chef Seafood Showcase, crafts and fine art from national artists, interactive art activities, Kids’ Zone, entertainment for all ages and a full music stage, there is something for everyone!
2026 headliners are Beach Bumz Band – a Jimmy Buffet & Trop Rock Tribute, and Greg Billings and the Stay Up Lates! See the full entertainment schedule below!General admission to the event is always FREE and the festival is DOG-FRIENDLY!
Saturday & Sunday, February 21st & 22nd
Find schedules and more information HERE.
Sunday
Tampa Bay Jewish Food Festival
Temple B’Nai Isreal, Clearwater
This native New Yorker often finds herself having powerful cravings for a piked high pastrami sandwich, a crunchy dill pickle, and a big old knish washed down with some Dr. Brown’s black cherry soda and maybe a black & white cookie, or three. Here’s a chance to savor original and delicious Jewish cuisine and have some fun too! Enjoy all your favorite Jewish foods including Carnegie Deli corned beef & pastrami sandwiches, Junior’s cheesecakes, matzoh ball soup potato knishes, noodle kugel, falafel pitas, stuffed cabbage, chopped liver, bagels, black & white cookies, babka loaves, and much, much more. Not responsible for overactive salivary glands…
Sunday, February 22nd @10:30am – 2:30pm
Find more information HERE.
**Concert Corner**
Fantasia & Anthony Hamilton
Benchmark International Arena, Tampa
Saturday, February 21st @8pm
Find tickets and more information HERE.
An Intimate Evening with David Foster & Katherine McPhee
Duke Energy Center for the Arts Mahaffey Theater, DTSP
Sunday, February 22nd @8pm
Find tickets and more information HERE.
Big bad Voodoo Daddy
Bilheimer Capital Theatre, Clearwater
Monday, February 23rd @8pm
Find tickets and more information HERE.
Have a great Top 10 weekend, everyone!
Cindy
