• Home
  • Events
  • Lifestyle
    • Home Decorating
    • Shopping
    • Foodie Hotspots
    • Outdoor Fun
    • Helpful Tips
  • Real Estate
    • Property Search
    • What is your Central Florida home worth now?
    • Central Florida
    • Selling a Home
      • Get You Home, Event, or Local Business Featured on the American Dream TV Show
      • Seller’s Guide: How to Sell Your Home for TOP DOLLAR
      • Exclusive Luxury Home Seller Program
      • Preparing Your Home to Sell
      • 6 Ways to Overcome the Emotions of Selling a Home
      • Things-to-Do when you’re NOT Selling your Home
      • Staging Your Home to Sell
    • Buying a Home
      • Buyer’s Guide: The Complete Guide to Buying a Home
      • I’m Thinking About Buying A Home
      • What to Expect During a Home Inspection
      • Don’t Choose a Mortgage Lender Based Only on the Interest Rate
      • Seven Ways to keep from Buying a Lemon
  • Communities
    • Audubon Park
    • Baldwin Park
    • Downtown Orlando
    • Winter Park
  • American Dream TV
    • Watch the Latest Episode
    • American Dream TV – Winter Park with Melissa Johnson
    • American Dream TV- Winter Park Media Kit
  • About
    • About Me
  • Skip to primary navigation
  • Skip to main content
  • Skip to primary sidebar

Florida Living

Fresh Squeezed- Florida Living

  • Home
  • Events
  • Lifestyle
    • Home Decorating
    • Shopping
    • Foodie Hotspots
    • Outdoor Fun
    • Helpful Tips
  • Real Estate
    • Property Search
    • What is your Central Florida home worth now?
    • Central Florida
    • Selling a Home
      • Get You Home, Event, or Local Business Featured on the American Dream TV Show
      • Seller’s Guide: How to Sell Your Home for TOP DOLLAR
      • Exclusive Luxury Home Seller Program
      • Preparing Your Home to Sell
      • 6 Ways to Overcome the Emotions of Selling a Home
      • Things-to-Do when you’re NOT Selling your Home
      • Staging Your Home to Sell
    • Buying a Home
      • Buyer’s Guide: The Complete Guide to Buying a Home
      • I’m Thinking About Buying A Home
      • What to Expect During a Home Inspection
      • Don’t Choose a Mortgage Lender Based Only on the Interest Rate
      • Seven Ways to keep from Buying a Lemon
  • Communities
    • Audubon Park
    • Baldwin Park
    • Downtown Orlando
    • Winter Park
  • American Dream TV
    • Watch the Latest Episode
    • American Dream TV – Winter Park with Melissa Johnson
    • American Dream TV- Winter Park Media Kit
  • About
    • About Me
  • Show Search
Hide Search

Fun Things-To-Do Week of May. 22nd, 2026

Melissa Johnson · May 22, 2026 ·

Come hang at the Blue Bamboo Center for the Arts with Jeff Rupert! Listen to great music in great company!

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. 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
  • Watercolor Floral Doodles, Autumn & Ro, Orlando, 1:30PM
  • Social Hour at the Corner Chophouse, Hannibal Square, Winter Park, 4-6PM
  • Sunset at the Zoo, Central Florida Zoo & Botanical Gardens, Sanford, 5-8PM
  • 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
  • Jeff Rupert Quartet, Blue Bamboo Center for the Arts, Winter Park, 8-10PM

Saturday, May. 23rd

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
  • 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
  • Name Day, Harry P. Leu Gardens, Orlando 9AM-5PM
  • Goat Yoga, Alaska Farms Orlando, 10:00AM, 11:15AM, & 1:30PM
  • Weekends at the Winery, Lakeridge Winery, 10AM-5PM
  • Flavors of Winter Park – Foodie Walking Tour, Chamber of Commerce, Winter Park, 10:45AM-1:15PM
  • The Mister Rogers Walking Tour + Boat, Chamber of Commerce Building, Winter Park, 12-3PM
  • 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
  • Imperial on Park: Live Music, Park Ave, Winter Park, 8PM

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


Sunday, May. 24th

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
  • Highlights Tour, Orlando Museum of Art, 1-2PM
  • 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
  • Thornton Park District Farmer’s Market, 10AM-3PM
  • The Winter Park Walking Tour, Winter Park City Hall, 12-1:30PM
  • The Mister Rogers Walking Tour + Boat, City of Winter Park Administrative Building, 12-3PM
  • 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

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


Monday, May. 25th

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
  • Crafters Social, Zymarium Meadery, Orlando, 6-8PM
  • Memorial Day Crown Royal Tasting, The Whiskey, Orlando, 6:30-8:30PM
  • Shining Starz Karaoke, Aloma Bowl, Winter Park, 7PM

Tuesday, May. 26th

It’s Tuesday!

  • Epic Paddle Board Adventures, Times & Events Vary
  • Scenic Boat Tour Around Winter Park, Morse Blvd, Downtown Winter Park, Times Very
  • The Winter Park Cultural Experience, Lyman Ave, Winter Park, 12-1:30PM
  • 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

Wednesday, May. 27th

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
  • Wine and Cheese Pairing, Simply Cheese, Orlando, 6:30
  • Book Swap Sip & Shop, The New Romantics, Orlando, 7-9PM

Thursday, May. 28th

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
  • The Winter Park Cultural Experience, Lyman Ave, Winter Park, 12-1:30PM
  • Learning Garden : Worm Race & Release, Martin Luther King, Jr Learning Garden, Winter Park, 4:30-5:15PM

Friday, May. 29th

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
  • Florida Stationery Fest, Florida Hotel & Conference Center, Orlando, 9AM-6PM
  • 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
  • Free Admission for Dads on Father’s Day, Orange County Regional History Center, 12-5PM, Sun. June 21st.
  • 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.

Primary Sidebar

About Me

Florida Living About Me

Hi there! I’m Melissa and a Florida girl through and through with a love-hate relationship with the sun.
Read More

Free Updates

Never miss a thing in Central Florida. Let me keep you in the loop. Sign up below to get a list of fun, local events delivered to your inbox weekly!

Sign up for Weekly Events

Contact MELISSA JOHNSON

  • 5039 Ocean Blvd
    Siesta Key, FL 34242
  • 407-681-4393
  • Hello@FloridaLivingwithMelissa.com
  • Email
  • Facebook
  • Instagram
  • Pinterest

Contact Me

Categories

  • Buying a Home
  • Communities
  • Events
  • Foodie Hotspots
  • Helpful Tips
  • Home Decorating
  • Lifestyle
  • Outdoor Fun
  • Real Estate
  • Selling a Home
  • Shopping

©Florida Living with Melissa | MLS License #261218544 | Copyright © 2026 | Brokered by eXp Realty, LLC| 407.681.4393 | Licensed Real Estate Brokerage in Florida | Privacy Policy