Looking for things to do in Winter Garden this May? Whether you’re a local or thinking about moving to the area, this month is packed with community events, live music, and family-friendly activities.

From the weekly farmers market to seasonal festivals, here’s your go-to guide for what’s happening in and around Winter Garden 👇

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🎶 Weekly Events in Winter Garden

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Fridays on the Plaza (Live Music Series)
📅 May 1, 8, 15, 22, 29 | ⏰ 7–9 PM
📍 Centennial Plaza Gazebo, Downtown Winter Garden
Enjoy free live music in the heart of downtown—perfect for a relaxed night out.

Winter Garden Farmers Market
📅 May 2, 9, 16, 23, 30 | ⏰ 8 AM–1 PM
📍 104 S. Lakeview Ave
One of the most popular things to do in Winter Garden, featuring local vendors, fresh produce, and artisan goods.

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🎉 Special Events Near Winter Garden

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Downtown Cinco De Mayo Block Party
📅 May 1 | ⏰ 6–9 PM
📍 McKey Street, Ocoee
Celebrate with music, food, and a lively community atmosphere.

Shop, Dine & Stroll Raffle (MAY-nia 2026)
📅 May 2 | All Day
📍 Historic Downtown Winter Garden
Support local businesses while exploring the charm of downtown.

A Toast to Mom: Mother’s Day Charcuterie Workshop
📅 May 3 | ⏰ 5:30–7:30 PM
📍 The Ancient Olive
A unique experience and one of the best Mother’s Day events in Winter Garden.

Cinco De Mayo Celebration at The Whole Enchilada
📅 May 5 | ⏰ 11 AM–11:30 PM
📍 129 W Plant St
An all-day fiesta with great food and drinks in Downtown Winter Garden.

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🌿 Mid-May Events in Winter Garden & Hamlin

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Hamlin Hoedown (Free Event)
📅 May 16 | ⏰ 10 AM–2 PM
📍 Lake District Green Space
A family-friendly event in the Hamlin area with activities for all ages.

Backyard Boots & Brews
📅 May 16 | ⏰ 3–7 PM
📍 Home State Brewing Co.
Enjoy local beer, live music, and a fun community vibe.

Central Florida Asian Cultural Festival
📅 May 17 | ⏰ 11 AM–4 PM
📍 Bill Breeze Park, Ocoee
Experience diverse cultures through food, performances, and local vendors.

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🇺🇸 Memorial Day Event

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Memorial Day Community Celebration
📅 May 25 | ⏰ 8:30–9:30 AM
📍 Veterans Memorial Park, Winter Garden
A meaningful way to honor and remember with the local community.

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Why People Love Living in Winter Garden

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Events like these are exactly why so many people are choosing to call Winter Garden home. There’s a strong sense of community, walkable downtown areas, and something happening year-round.

If you’re searching for homes in Winter Garden or nearby areas like Ocoee or Hamlin, this lifestyle is a big part of what you’re investing in.

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