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Festivals in Windermere, FL

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3rd Thursday Opening Night Reception (November)
Thu, Nov 20, 6:00 PM
Orlando · CityArts
3rd Thursday Opening Night Reception (November)
Thu, Nov 20, 6:00 PM
Orlando · CityArts
VEGAN BLOCK PARTY - ORLANDO
Sat, Feb 7, 3:00 PM
Orlando · Luminary Green
VEGAN BLOCK PARTY - ORLANDO
Sat, Feb 7, 3:00 PM
Orlando · Luminary Green
Swoons Fest 2026
Sun, Jan 18, 12:00 PM
Winter Park · Azalea Lodge at Mead Botanical Garden
Swoons Fest 2026
Sun, Jan 18, 12:00 PM
Winter Park · Azalea Lodge at Mead Botanical Garden
Legend of the Geezers 2026
Tue, Jan 13, 10:00 AM
Apopka · City of Apopka Camp Wewa
Legend of the Geezers 2026
Tue, Jan 13, 10:00 AM
Apopka · City of Apopka Camp Wewa
Faded Kingdom Beer Festival - 2026
Sat, Jan 31, 12:00 PM
Orlando · Tactical Brewing
Faded Kingdom Beer Festival - 2026
Sat, Jan 31, 12:00 PM
Orlando · Tactical Brewing
Taste of Hannibal Square 2025
Thu, Nov 20, 4:00 PM
Winter Park · West New England Avenue
Taste of Hannibal Square 2025
Thu, Nov 20, 4:00 PM
Winter Park · West New England Avenue
407 FEST
Sat, Nov 22, 5:00 PM
Orlando · Lobos Coffee Roasters
407 FEST
Sat, Nov 22, 5:00 PM
Orlando · Lobos Coffee Roasters
Fete Minuet: The Sequel 2026
Sun, Jan 18, 6:00 PM
Winter Park · Winter Park Farmers' Market
Fete Minuet: The Sequel 2026
Sun, Jan 18, 6:00 PM
Winter Park · Winter Park Farmers' Market
Orlando Praise Fest (2nd Annual)
Sat, Nov 22, 6:00 PM
Orlando · 4425 N Powers Dr
Orlando Praise Fest (2nd Annual)
Sat, Nov 22, 6:00 PM
Orlando · 4425 N Powers Dr
Jollywood Film Festival
Wed, Nov 12, 9:00 AM + 1 more
Orlando · Touchstar Cinemas - Southchase 7
Jollywood Film Festival
Wed, Nov 12, 9:00 AM + 1 more
Orlando · Touchstar Cinemas - Southchase 7
Deck The District on Church Holiday Event
Thu, Nov 20, 6:00 PM
Orlando · 54 W Church St
Deck The District on Church Holiday Event
Thu, Nov 20, 6:00 PM
Orlando · 54 W Church St
Sales end soon
Casselberry's 15th Annual Food and Wine Festival
Monday at 6:00 PM
Casselberry · Lake Concord Park
Sales end soon
Casselberry's 15th Annual Food and Wine Festival
Monday at 6:00 PM
Casselberry · Lake Concord Park
Goddessgiving: A Mythical Fall Gathering (Clermont/Four Corners)
Sat, Nov 15, 12:30 PM
Clermont · Tradd's Landing
Goddessgiving: A Mythical Fall Gathering (Clermont/Four Corners)
Sat, Nov 15, 12:30 PM
Clermont · Tradd's Landing
Just added!
Oranges & Ornaments: A Festival of Trees (Friday)
Fri, Nov 21, 5:00 PM
Winter Garden · The Winter Garden Heritage Foundation - Healthy West Orange Heritage and Cultural Center
Just added!
Oranges & Ornaments: A Festival of Trees (Friday)
Fri, Nov 21, 5:00 PM
Winter Garden · The Winter Garden Heritage Foundation - Healthy West Orange Heritage and Cultural Center
Just added!
Afrofeteness Experience Orlando
Tue, Nov 18, 7:00 PM
Winter Park · 2716 Forsyth Rd suite 112
Just added!
Afrofeteness Experience Orlando
Tue, Nov 18, 7:00 PM
Winter Park · 2716 Forsyth Rd suite 112
A Season of Celebration - General Admission
Sat, Nov 15, 10:00 AM + 8 more
Orlando · Orlando Museum of Art
A Season of Celebration - General Admission
Sat, Nov 15, 10:00 AM + 8 more
Orlando · Orlando Museum of Art
Sales end soon
Krush Brau Oktoberfest 2025 (Biggest German Beer Garden in the US - 10 AC)
Today at 4:00 PM + 6 more
Kissimmee · Krush Brau Park Portal Immersion Center
Sales end soon
Krush Brau Oktoberfest 2025 (Biggest German Beer Garden in the US - 10 AC)
Today at 4:00 PM + 6 more
Kissimmee · Krush Brau Park Portal Immersion Center
Oranges & Ornaments: A Festival of the Trees with Mrs. Claus
Sat, Nov 22, 8:00 AM
Winter Garden · The Winter Garden Heritage Foundation - Healthy West Orange Heritage and Cultural Center
Oranges & Ornaments: A Festival of the Trees with Mrs. Claus
Sat, Nov 22, 8:00 AM
Winter Garden · The Winter Garden Heritage Foundation - Healthy West Orange Heritage and Cultural Center
2025 Orlando Korea Festival
Fri, Dec 12, 3:00 PM + 1 more
Orlando · 7000 Winegard Rd
2025 Orlando Korea Festival
Fri, Dec 12, 3:00 PM + 1 more
Orlando · 7000 Winegard Rd
A Cookie Monster Xmas
Fri, Dec 12, 10:00 PM
Orlando · D'Junction Island Bar and Restaurant
A Cookie Monster Xmas
Fri, Dec 12, 10:00 PM
Orlando · D'Junction Island Bar and Restaurant

Trends in Windermere

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Frequently asked questions about Windermere

What are the best festival events to attend?

According to Eventbrite, the best festival events are:

3rd Thursday Opening Night Reception (November)

VEGAN BLOCK PARTY - ORLANDO

Swoons Fest 2026

Legend of the Geezers 2026

Which events are currently trending in Windermere?

The trending searches this month in Windermere are:

new years eve parties

Which festival events are coming up?

Discover the best festival events happening soon – you don't want to miss them:

Krush Brau Oktoberfest 2025 (Biggest German Beer Garden in the US - 10 AC)

Casselberry's 15th Annual Food and Wine Festival

Jollywood Film Festival

A Season of Celebration - General Admission