Osceola with Kids

Osceola with Kids Working Mom of 4 | Exploring Osceola County
Kissimmee • St. Cloud • Poinciana • Central FL
Weekend Guide every Thursday 🗓️
📩 [email protected]

Whether you’re planning a family day out, a date night, or just looking for something fun to do, we’ve got you covered. ...
09/10/2026

Whether you’re planning a family day out, a date night, or just looking for something fun to do, we’ve got you covered. Check what’s happening around Osceola County this weekend! 🎉

Save this guide, send it to your weekend crew, and start making those plans!



September 12th
7:30AM
St. Cloud Lakefront Park

September 12th
10:30AM
St. Cloud Library

September 12th
10AM - 3PM
Casa del Artesano

September 12th
10:30AM - 1PM
Skate Reflections

September 12th
11AM
Violet Garage

September 12th
11AM
Barnes and Noble Lake Nona

September 12th
1PM
Nosso Quintal Brazilian Bar & Grill

September 12th
2PM - 7PM
Kissimmee Lakefront Park

September 12th
2PM
Gymboree Lake Nona

September 12th
3PM - 4PM
Loumart Creative Studio

September 13th
12PM - 2PM
Violet’s Garage

September 13th
2:30PM - 4:30PM
Ex Animo Creations

September 13th
2:30PM
Pa’ Pikar Latin Grill

Hi! 👋 I’m Stephany, a working mom of 4, wife, and the person behind Osceola With Kids. ❤️If you’re new here, welcome! An...
09/09/2026

Hi! 👋 I’m Stephany, a working mom of 4, wife, and the person behind Osceola With Kids. ❤️

If you’re new here, welcome! And if you’ve been here for a while… hi again! It’s been about a year since I properly introduced myself, and a LOT has changed. 🥹

When I started Osceola With Kids, I wanted to find fun things to do with my family and share the places I discovered along the way. What started as a little idea has grown into a community of families looking for things to do, places to explore, and memories to make around Osceola County and Central Florida.

These days, you’ll find me sharing:
🛝 Family-friendly places & activities
📍 Local events around Kissimmee, St. Cloud, Poinciana, Celebration & beyond
🌴 Central Florida day trips & adventures
🗓️ Weekend Guide every Thursday

And as a mom of 4, I know how valuable it is to find something that the WHOLE family can actually enjoy. 😅

So whether you’re in Kissimmee, St. Cloud, Poinciana, Celebration, or anywhere around Central Florida, I’m so glad you’re here!

Now I want to meet YOU 👇
📍 Where are you following from, and what’s your family’s favorite place to visit around Osceola County?

Let’s explore Central Florida together! 🫶

09/04/2026

Handmade Custom Crayons aren’t just crayons… they’re little works of art! Handmade in the cutest shapes, they make coloring so much more fun for kids. They’re perfect for little hands, encourage creativity, and even make a unique gift. Because let’s be honest… coloring is way more exciting when your crayons look like this!

Looking for something fun to do with the kids this Labor Day weekend? 👀 From storytimes and creative workshops to market...
09/03/2026

Looking for something fun to do with the kids this Labor Day weekend? 👀 From storytimes and creative workshops to markets, festivals, cruises, art camp, and more; there’s plenty happening around Osceola! 🇺🇸

FRIDAY, SEPTEMBER 4
🍪 Cookies with a Speech Therapist
12PM–1PM | Gymboree Nona

🚤 Afternoon & Sunset Cruise
Old Florida Riverboat
Sept. 4 & 6

🇺🇸 Labor Day Weekend Celebration
Promenade at Sunset Walk
Sept. 4–7

SATURDAY, SEPTEMBER 5
🔨 Home Depot Kids Workshop
9AM–12PM | Any Home Depot Store
*Registration Required

🎉 Kidtopia Fest
10AM–2PM | Orlando, FL

🎨 Taller de Resina
10AM–3PM | Casa del Artesano

📖 Storytime: Little Blue Truck Lost and Found
1PM | Barnes & Noble Lake Nona

🛍️ Sunset Market
1PM–5PM | Violet’s Garage

✨ DIY Charm Bookmarks
2PM–4PM | Lucky Goat Coffee Celebration

🍔 Labor Day Food Festival
Food Trucks Heaven

SUNDAY, SEPTEMBER 6
🪑 The Big Red Chair
Chris Lyle Aquatic Center

MONDAY, SEPTEMBER 7
🎨 Labor Day Holiday Art Camp
9AM–4PM | Ex Animo Creations

SAVE THIS POST so you have a list of things to do all Labor Day weekend! 🇺🇸

📲 Tag a mom, dad, or friend who needs weekend plans! 👇

🍂🎃 Best Fall Festivals in Central Florida 2026 🍁Looking for fall festivals, pumpkin patches, hayrides & family fun in Ce...
08/31/2026

🍂🎃 Best Fall Festivals in Central Florida 2026 🍁

Looking for fall festivals, pumpkin patches, hayrides & family fun in Central Florida? These fall events near Orlando and Osceola County are perfect for making the most of the season with the kids! 🧡

Here are some must-visit fall festivals happening this fall:

🎃 Showcase of Citrus
📅 September 18 - October 31
📍 Clermont, FL

🎃 Amber Brooke Farm
📅 September 18 - November 22
📍 Eutis, FL

🎃 Lil Bit of Life
📅 September 21
📍 Mount Dora, FL

🎃 Green Meadows Farm
📅 September 26 - November 8
📍 Kissimmee, FL

🎃 Great Scott
📅 September 26 - November 15
📍 Mount Dora, FL

🎃 Southern Hill Farms
📅 September 26 - November 22
📍 Clermont, FL

🎃 Hastings Ranch & Farm
📅 October 11 - October 25
📍 St. Cloud, FL

🍁Think pumpkin patches, fall treats, hayrides, farm animals, games, live entertainment, photo ops & tons of autumn fun for the whole family! 🍂

📌 SAVE this list for your fall bucket list
👩‍👩‍👧 TAG a friend who loves fall family activities

🎉 WEEKEND PLANS? WE’VE GOT YOU! ☀️🎨Looking for something fun to do with the kids this weekend? 👀 From homeschool activit...
08/28/2026

🎉 WEEKEND PLANS? WE’VE GOT YOU! ☀️🎨

Looking for something fun to do with the kids this weekend? 👀 From homeschool activities and storytimes to creative classes, family playdates, live music, and even a dive-in movie; there’s plenty happening around Osceola County!

FRIDAY, AUGUST 28
📚 Homeschool Recreation Open House
10AM–1PM | St. Cloud Civic Center

🎂 It’s Gymbo’s B-Day!
12PM | Gymboree Nona

🎶 80’s R&B in the Garden
6PM–9PM | Hunter Arms Hotel

SATURDAY, AUGUST 29
🏊 Pool Pals Story Time
9AM–10AM | Bob Makinson Aquatic Center

🔨 Lowe’s Kids Workshop
10AM–1PM | Any Lowe’s Store
*Registration Required

🧶 Taller de Crochet
11AM | Casa del Artesano

🚒 Fire Ready Together
11AM–12:30PM | Buenaventura Lakes Library

🕯️ Mom & Daughter Candle Making Class
11AM–1PM | Oak Street Park Community Center

🎨 Drawing Class for Kids
12:30PM–1:30PM | Loumart Creative Studio

📖 Storytime: Awesome Friendly Spooky Stories 👻
2PM | Barnes & Noble Lake Nona
*Registration Required

🎨 Couples Paint Night
6PM–8PM | Ex Animo Creations

🤠 Country Night
6PM–9PM | Nona Adventure Park

🥁 Steel Drum Sunset Cruise
7PM–8:30PM | Old Florida Riverboat

SUNDAY, AUGUST 30
🛝 OWK Playdate
10:30AM–12PM | Kissimmee Lakefront Park

🎬 Dive-In Movie
7PM | The Allen Apartments

SAVE THIS POST so you have a list of things to do all weekend!

📲 Tag a mom, dad, homeschool family, or friend who needs weekend plans! 👇

08/26/2026

🍕 A simple, fun activity that kids absolutely love: family pizza night! ❤️ Everyone got to make their pizza just the way they liked it.

These are definitely the simple moments that turn into the best memories. 🥰

Are you team cheese, pepperoni, or a little bit of everything? 👀🍕

08/25/2026

A little recap of our time at the Florida Kids and Family Expo 2026! 🎉💗

Thanks to MyCentralFloridaFamily . com we had so much fun exploring the different activities, making memories, and enjoying all the fun together.

The expo only happens once a year, so if you missed it this time, save it for next August! 🗓️🎉

08/25/2026

A FREE family day at Bok Tower Gardens ?! 🌿🔔

We spent the day exploring the gardens, letting the kids play, and finally making our way to the beautiful Singing Tower. It was such a peaceful and fun way to enjoy one of the last days of summer! 😍🌳🦋

And the best part: through Wawa Summer Fun Days, admission is FREE on the last Thursday and Friday of each month through August! 🎉

📍 Bok Tower Gardens
🎟️ Free admission with pre-registration

Save this for your next family adventure! And follow me for more free & fun things to do with kids around Central Florida. 🫶🏼

🎉 Your weekend starts here! Here’s what’s happening around Osceola County! ☀️🎪Thursday, August 20⭐ Starry Night — 6:30PM...
08/20/2026

🎉 Your weekend starts here! Here’s what’s happening around Osceola County! ☀️🎪

Thursday, August 20
⭐ Starry Night — 6:30PM–8:30PM | Poinciana Library

Friday, August 21
🐚 Seashells & Lattes — 6:30PM–8:30PM | Foxtail Coffee Legacy Village
✨ Back 2 School Glow Party — 7PM–10PM | Ice Factory of Central FL
😂 Comedy on Broadway — 8PM–9:30PM | Violet’s Garage
🤠 Reggae Rodeo — Time varies | 1881 Restaurant & Bar

Saturday, August 22
🏃 Kissimmee Walk & Run Club — 7:30AM | Kissimmee Lakefront Park
🎨 Taller de Resina — 10AM–3PM | Casa del Artesano
🛍️ Kingdom Creations Market — 10AM–4PM | Lake Nona High School
🎪 Central Florida Kids & Family Expo — 10AM–4PM | Orange County Convention Center
📚 Tertulia Cuatro Gatos para Niños — 10:30AM–12:30PM | Buenaventura Lakes Library
🌳 City of Kissimmee Parks & Recreation Open House — 11AM–2PM | Oak Street Park Community Center
🧙 Magik & Mythk Festival — 11AM–6PM | Osceola Heritage Park
🌮 Saturday Family Fun — 12PM–11:30PM | Food Trucks Heaven
📖 Storytime: The Coquies Still Sing — 1PM | Barnes & Noble Lake Nona
🐴 Moonlight Trail Ride — 6PM–9:30PM | The Barn - St. Cloud

Sunday, August 23
♟️ Summer Chess Championship — 12PM–5:30PM | West Osceola Library
🦄 The Unicorn Skate Jam — 1:30PM–4:30PM | Skate Reflections

Saturday & Sunday, August 22–23
🎪 Central Florida Kids & Family Expo — 10AM–4PM | Orange County Convention Center



👇 Which event is making it onto your weekend plans? Tell us in the comments!

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