Where community, charm and sunshine come together just minutes from the magic

One of the biggest surprises for people moving near Disney is discovering that the magic isn’t just in the parks… it’s in the neighborhoods. Winter Garden, Horizon West and Windermere are full of vibrant local events that bring the community together all year long.

Farmers markets, outdoor concerts, food truck nights, seasonal festivals, charity runs, art walks, cultural events… these towns are alive with energy, connection and small town warmth.

Here are the best events locals enjoy throughout the year… the ones that make the Disney Bubble feel like home.

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🌽 1. Winter Garden Farmers Market

Every Saturday • Downtown Winter Garden

One of the top farmers markets in Florida… and the heart of Winter Garden life.

Expect:

• Fresh produce
• Artisanal foods
• Local honey and baked goods
• Flowers and plants
• Live music
• Family friendly atmosphere

Locals grab coffee, stroll Plant Street, meet friends and enjoy sunshine-filled Saturdays.

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🎶 2. Spring Fever in the Garden Festival

Downtown Winter Garden

A gorgeous spring celebration filled with:

• Flower displays
• Garden vendors
• Art booths
• Live music
• Family activities

It’s one of the town’s most beloved annual events.

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🍫 3. Winter Garden Holiday Market & Light Up Winter Garden

November & December

The entire town transforms into a holiday wonderland.

Expect:

• Charming Christmas booths
• Live music
• Tree lighting
• Kids activities
• Stunning light displays

It’s pure small town holiday magic.

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🥤 4. Fridays on the Plaza

Downtown Winter Garden

A weekly outdoor live music series.

Locals love:

• Small-town charm
• Free concerts
• Family friendly environment
• Relaxing date-night energy

Bring a chair… let the music do the rest.

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🚴 5. Winter Garden’s Cruz-N Car Show

Third Saturday of each month

A classic, family-friendly event for car lovers.

Expect:

• Vintage cars
• Hot rods
• Food vendors
• Retro vibes

Super nostalgic and fun.

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🎬 6. Movies on the Lawn (Hamlin)

Horizon West • Hamlin Town Center

One of Horizon West’s most popular family events.

Enjoy:

• Big outdoor movie screen
• Free entry
• Picnic blankets and lawn chairs
• Food stalls and treats

Perfect for family nights under the stars.

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🍔 7. Hamlin Food Truck Fridays

Horizon West • Hamlin

A beloved local tradition.

Expect:

• Dozens of gourmet food trucks
• Live music
• Kids play areas
• Amazing sunset views

It’s a casual, laid-back community gathering.

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🎨 8. Hamlin Artisan & Farmers Markets

Horizon West

These markets bring together:

• Local makers
• Craft vendors
• Specialty foods
• Seasonal pop ups

It’s become a signature Horizon West weekend vibe.

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🧁 9. Horizon West Fest

Annual Event

A big, energetic community festival celebrating the rapid growth of the area.

Highlights:

• Vendor booths
• Local businesses
• Food and drinks
• Kids activities
• Live performances

A great intro event for new residents.

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🚤 10. Windermere’s Monthly Farmers Market

Downtown Windermere

Smaller and more intimate than Winter Garden’s market, but full of charm.

Expect:

• Organic produce
• Fresh baked goods
• Local artisans
• Plant vendors

Quiet, upscale and very neighborhood friendly.

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🎨 11. Windermere Art Affair

Annual Event

A classy art festival featuring:

• Fine art
• Local and national artists
• Sculptures and mixed media
• Gourmet food vendors

It reflects the elegant energy of Windermere.

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🧺 12. Windermere Family Food Truck Nights

Monthly

A favorite for families who want a relaxed evening outdoors.

Expect:

• Rotating food trucks
• Picnic areas
• Kids activities
• Beautiful old oak trees and warm breezes

Relaxed, friendly and laid back.

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🔔 13. Windermere Holiday Events & Tree Lighting

December

Windermere goes full cozy-holiday mode.

Enjoy:

• Tree lighting
• Live music
• Hot cocoa
• Holiday crafts
• Picturesque small town decor

It’s peaceful and postcard perfect.

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🎭 14. Garden Theatre Live Shows & Community Events

Downtown Winter Garden

Not just performances… but community gatherings.

Locals attend:

• Broadway-style productions
• Local plays
• Holiday shows
• Special events and galas

It adds arts and culture to the heart of the Disney Bubble.

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🎗️ 15. 5Ks, Fun Runs & Charity Events

Throughout Winter Garden, Hamlin and Windermere

Popular annual races include:

• Run for the Trees
• Hamlin Harvest 5K
• Winter Garden 10K Series
• Local charity fun runs

They bring the community together for fitness, fun and fundraising.

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🎡 16. Celebration Meets Horizon West Events (Seasonal Crossovers)

As these areas grow, more cross-community events pop up like:

• Spring markets
• Craft fairs
• Outdoor concerts
• Seasonal celebrations

The region becomes one big connected Disney-adjacent hub.

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🌟 Why Local Events Matter to Disney Relocators

Because this is the part of the Disney Bubble most people don’t know exists until they visit…

The sunshine markets.
The outdoor concerts.
The food truck nights.
The small town festivals.
The family-friendly community magic.

Disney brings the “wow”…
But Winter Garden, Horizon West and Windermere bring the warmth.

This guide makes buyers feel the lifestyle… not just see it.

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⭐ Ready to Live in the Heart of These Magical Local Communities?

If you’re dreaming of sunshine weekends, neighborhood events and Disney magic just down the road… I’d love to help you find your perfect home in the Disney Bubble.

👉 Schedule your Disney Bubble Buyer Consultation today.
Let’s make this lifestyle your reality.