Events Calendar
Upcoming events in Winter Garden, Windermere, Oakland & West Orange County
April 2026
APR
3
🎪
Fridays on the Plaza
8 AM–1 PM · Downtown Interactive Fountain & Pavilion · Every Friday
Details →
APR
4
APR
7
APR
9
🏗️
Development Review Committee Meeting
6:30 PM · City Hall Chambers · City of Winter Garden
Details →
APR
10
🐣
Easter Kids' Craft at the Farmers Market
7 PM–9 PM · Downtown Pavilion · Special evening market event
Details →
APR
10
🎪
Fridays on the Plaza
8 AM–1 PM · Downtown Interactive Fountain & Pavilion · Every Friday
Details →
APR
11
🌸
Spring Fever in the Garden
Annual spring arts & garden festival · Downtown Winter Garden
Details →
APR
11
APR
14
APR
14
APR
17
🎪
Fridays on the Plaza
8 AM–1 PM · Downtown Interactive Fountain & Pavilion · Every Friday
Details →
APR
18
APR
21
🏛️
Oakland Town Commission Regular Meeting
6:30 PM · Oakland Meeting Hall · Town of Oakland
Details →
APR
22
🌎
Earth Day — Tote Bag Giveaway
Free reusable tote bags while supplies last · Winter Garden City Hall
Details →
APR
24
🎪
Fridays on the Plaza
8 AM–1 PM · Downtown Interactive Fountain & Pavilion · Every Friday
Details →
APR
25
APR
28
APR
30
May 2026
MAY
1
🎪
Fridays on the Plaza
8 AM–1 PM · Downtown Interactive Fountain & Pavilion · Every Friday
Details →
MAY
2
MAY
8
🎪
Fridays on the Plaza
8 AM–1 PM · Downtown Interactive Fountain & Pavilion · Every Friday
Details →
MAY
9
MAY
15
🎪
Fridays on the Plaza
8 AM–1 PM · Downtown Interactive Fountain & Pavilion · Every Friday
Details →
MAY
16
MAY
22
🎪
Fridays on the Plaza
8 AM–1 PM · Downtown Interactive Fountain & Pavilion · Every Friday
Details →
MAY
23
MAY
29
🎪
Fridays on the Plaza
8 AM–1 PM · Downtown Interactive Fountain & Pavilion · Every Friday
Details →
MAY
30
June 2026
JUN
5
🎪
Fridays on the Plaza
8 AM–1 PM · Downtown Interactive Fountain & Pavilion · Every Friday
Details →
JUN
6
JUN
12
🎪
Fridays on the Plaza
8 AM–1 PM · Downtown Interactive Fountain & Pavilion · Every Friday
Details →
JUN
13
JUN
19
🎪
Fridays on the Plaza
8 AM–1 PM · Downtown Interactive Fountain & Pavilion · Every Friday
Details →
JUN
20
JUN
26
🎪
Fridays on the Plaza
8 AM–1 PM · Downtown Interactive Fountain & Pavilion · Every Friday
Details →
JUN
27
July 2026
JUL
3
🎪
Fridays on the Plaza
8 AM–1 PM · Downtown Interactive Fountain & Pavilion · Every Friday
Details →
JUL
4
JUL
10
🎪
Fridays on the Plaza
8 AM–1 PM · Downtown Interactive Fountain & Pavilion · Every Friday
Details →
JUL
11
JUL
17
🎪
Fridays on the Plaza
8 AM–1 PM · Downtown Interactive Fountain & Pavilion · Every Friday
Details →
JUL
18
JUL
24
🎪
Fridays on the Plaza
8 AM–1 PM · Downtown Interactive Fountain & Pavilion · Every Friday
Details →
JUL
25
JUL
31
🎪
Fridays on the Plaza
8 AM–1 PM · Downtown Interactive Fountain & Pavilion · Every Friday
Details →
Have an event to add? Send the details to
hello@gmwgnews.com
and we’ll add it to an upcoming edition.