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Fun Things-To-Do Week of May. 15th, 2026

Melissa Johnson · May 15, 2026 ·

Hop on over to Hannibal Square for the annual Hop Hannibal! Enjoy community, food and shopping!

I couldn’t be more excited to welcome you to the “Weekly Events” section of Florida Living with Melissa! Here is this week’s complete list of fun things-to-do in Central Florida.  

Have a great week and remember to tag us on Instagram or Facebook. 
We’d love to see how you are enjoying all the things you’re loving about Florida Living!

THIS WEEK’S FUN THINGS-to-DO:


Friday, May. 15th

Happy Friday!

  • Epic Paddle Board Adventures, Times & Events Vary
  • Scenic Boat Tour Around Winter Park, Morse Blvd, Downtown Winter Park, Times Very
  • The Y2K Pilates Social, Primrose Lanes, Orlando, 9AM-12PM
  • Indoor Pickleball Open Courts and Lessons, Gateway Church, Winter Park, 9AM-1PM
  • Social Hour at the Corner Chophouse, Hannibal Square, Winter Park, 4-6PM
  • Bites Night, BarkHaven, Orlando, 5-9PM
  • Deland Artisan Alley Farmer’s Market 6-9PM
  • Sounds of Wekiva, Live Music Event, Wekiva Island, 7PM
  • Shining Starz Karaoke, Aloma Bowl, Winter Park, 7PM

Saturday, May. 16th

Happy Saturday! What fun things are you doing?

  • Winter Park Farmer’s Market 8AM-1PM
  • Scenic Boat Tour Around Winter Park, Morse Blvd, Downtown Winter Park, Times Very
  • Party for the Planet!, Central Florida Zoo & Botanical Gardens, Sanford, 9AM-4PM
  • Everoak Farm Stand, Orlando, 9AM-1PM
  • Epic Paddle Board Adventures, Times & Events Vary
  • Public Ice Skating, Ice Den RDV, Times Vary
  • Yoga in the Park, $15, Mead Botanical Garden, Winter Park, 9-10AM
  • Goat Yoga, Alaska Farms Orlando, 10:00AM, 11:15AM, & 1:30PM
  • Weekends at the Winery, Lakeridge Winery, 10AM-5PM
  • Sunflower Festival, Amber Brooke Farms, Eustis, 10AM-6PM
  • Saturday Exhibition Highlights Docent-Led Tour, Rollins Museum of Art, Winter Park, 1PM & 3PM
  • Social Hour at the Corner Chophouse, Hannibal Square, Winter Park, 2:30-4PM
  • Brewlando Family Day, Hoffner Ave, Orlando, 4-9PM
  • Glow Golf!, Winter Park Pines Driving Range, 7:30-9:30PM
  • Imperial on Park: Live Music, Park Ave, Winter Park, 8PM
  • Greg Diaz & The Art of Imagination Quintet, Blue Bamboo Center for the Arts, Orlando, 8-10PM

WEEKEND OPEN HOUSES, Complete list of Scheduled Open Houses, Various Times


Sunday, May. 17th

Sunshine Sunday!

  • Maitland Farmer’s Market 8:30AM-1:30PM
  • Scenic Boat Tour Around Winter Park, Morse Blvd, Downtown Winter Park, Times Very
  • Epic Paddle Board Adventures, Times & Events Vary
  • Goat Yoga, Alaska Farms Orlando, 10:00AM, 11:15AM, & 1:30PM
  • Weekends at the Winery, Lakeridge Winery, 11AM-5PM
  • Orlando Farmer’s Market Lake Eola Park 10AM
  • Lakeside Yoga – Self-Care Sunday, Harry P. Leu Gardens, Orlando, 10-11AM
  • Thornton Park District Farmer’s Market, 10AM-3PM
  • Sunflower Festival, Amber Brooke Farms, Eustis, 10AM-6PM
  • In Patriotic Fashion: The Fun and Quirky Side of Centennial Celebrations, The History Center, Orlando, 2-4PM
  • Growin’ Through It Head Planter Workshop, Harry P. Leu Gardens, Orlando, 2-4PM
  •  Hall of Fame Show, Blue Bamboo Center for the Arts, Orlando, 3-5PM
  • Social Hour at the Corner Chophouse, Hannibal Square, Winter Park, 2:30-4PM
  • Yoga in the Park, $15, Mead Botanical Garden, Winter Park, 4-5PM
  • The Notebook, Dr. Phillips Center for the Performing Arts, Orlando, 8PM

WEEKEND OPEN HOUSES, Complete list of Scheduled Open Houses, Various Times


Monday, May. 18th

Magical Monday

  • Epic Paddle Board Adventures, Times & Events Vary
  • Scenic Boat Tour Around Winter Park, Morse Blvd, Downtown Winter Park, Times Very,
  • Social Hour at the Corner Chophouse, Hannibal Square, Winter Park, 4-6PM
  • Audubon Community Market 5-9PM
  • C-M Bakari Sour Dough Bread, Audubon Community Market, 5-9PM (Sells Out Fast, Pre-Order Before Event)
  • Audubon Community Market, Audubon, Orlando, 5-9PM
  • Shining Starz Karaoke, Aloma Bowl, Winter Park, 7PM

Tuesday, May. 19th

It’s Tuesday!

  • Epic Paddle Board Adventures, Times & Events Vary
  • Scenic Boat Tour Around Winter Park, Morse Blvd, Downtown Winter Park, Times Very
  • Social Hour at the Corner Chophouse, Hannibal Square, Winter Park, 4-6PM
  • Trivia Night!, Bonfire at Winter Park Pines, Winter Park, 7-9PM
  • Tasty Takeover- Food Truck Block Party, The Milk District, Orlando E. Robinson St. 6:30-10PM
  • AJ Chocolate House: Ladies Night, AJ Chocolate House, Park Ave, Winter Park, 6-10PM
  • Craft a Felt Photocard Holder, GB’s Bottle Shop, Orlando, 6-8PM
  • The Book Club x Cookbook Club: On Eating, Authentic Books, Orlando, 6:30PM
  • Celebrate 250 Years of The United States, Dr. Phillips Center for the Performing Arts, Orlando, 7:30PM

Wednesday, May. 20th

Wednesday, latin for “it’s almost the weekend!” 

  • Epic Paddle Board Adventures, Times & Events Vary
  • Scenic Boat Tour Around Winter Park, Morse Blvd, Downtown Winter Park, Times Very
  • Goat Yoga, Alaska Farms Orlando, 5:30PM
  • Social Hour at the Corner Chophouse, Hannibal Square, Winter Park, 4-6PM
  • Wine Down Wednesdays at the Alfond Inn, Winter Park, 4-9PM
  • Ladies Night, The Wine Room on Park Avenue, 6:30PM
  • Around the World Cheese Tasting, Simply Cheese, Winter Park, 6:30

Thursday, May. 21st

Thursday: The day that says, “You got this!”

  • Epic Paddle Board Adventures, Times & Events Vary
  • Scenic Boat Tour Around Winter Park, Morse Blvd, Downtown Winter Park, Times Very
  • Hop Hannibal, Hannibal Square, Winter Park, 4-7PM
  • Taste of Altamonte, Cranes Roost Park, Altamonte Springs, 6:30-9:30PM
  • Music at the Casa: Solomon Jaye, Casa Feliz, Winter Park, 6:30-8:30PM

Friday, May. 22nd

Happy Friday!

  • Epic Paddle Board Adventures, Times & Events Vary
  • Scenic Boat Tour Around Winter Park, Morse Blvd, Downtown Winter Park, Times Very
  • Indoor Pickleball Open Courts and Lessons, Gateway Church, Winter Park, 9AM-1PM
  • Watercolor for Beginners: Oranges, Harry P. Leu Gardens, Orlando, 1-3PM
  • Social Hour at the Corner Chophouse, Hannibal Square, Winter Park, 4-6PM
  • Deland Artisan Alley Farmer’s Market 6-9PM
  • Sounds of Wekiva, Live Music Event, Wekiva Island, 7PM
  • Shining Starz Karaoke, Aloma Bowl, Winter Park, 7PM

Upcoming Events
SAVE THE DATE & BOOK EARLY

  • Science Night Live, Orlando Science Center, Orlando, 8-11:30PM, Sat. May 30th
  • Poetry Day, Harry P. Leu Gardens, Orlando, 10AM-1PM, Sat. May 30th
  • United Groove: An Evening of Funk, Blues and Soul, United Groove: An Evening of Funk, Blues and Soul, Winter Park, 7PM, Tues. June 11th
  • Megan Moroney, Kia Center, Orlando, 7PM, Thurs. July 16th BUY TICKETS SOON

Want your event featured in our weekly event’s list? Email Melissa at Hello@FloridaLivingwithMelissa.com.

Filed Under: Events Tagged With: central florida, central florida local events, fun things to do, orlando, orlando local business, shop local, things to do, winter park florida

About Melissa Johnson

Hi There! I'm Melissa Johnson.
I work with residents in Central Florida who want to get information about fun activities in and around Central Florida.

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