Happening Next in Winter Park

Name: Orlando Gay Chorus Presents: "Love Is...A Drag" Cabaret
Start: 2026-02-21
Location: Blue Bamboo Center For The Arts

Upcoming Live Music Events

VOCES8 in Winter Park

Knowles Memorial Chapel 15 Feb 2026

ART

Cassadee Pope at Conduit

Conduit 8 Mar 2026

Greg Parnell Valentine Quintet | Feb 14 | Blue Bamboo

460 E. New England Ave., Winter Park, FL, United States, Florida 32789 14 Feb 2026

MUSIC

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Upcoming Valentine's Day Events

Candlelight: Valentine's Day Special - Winter Park

1300 S Denning Dr, Winter Park, FL 12 Feb 2026

CANDLELIGHT-CONCERTS

FREE Valentine's Concert in the Park- Swing into Romance

Central Park In Winter Park, Florida 13 Feb 2026

MUSIC

Valentines’s Ramen Bowl Date

2354 Winter Woods Blvd Suite 2310, Winter Park, FL 14 Feb 2026

VALENTINES-DAY

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Upcoming Festivals Events

1st Annual Holler Ford Racing Showcase

1875 South Orlando Avenue, Maitland, FL, United States, Florida 32751 14 Mar 2026

SPORTS

Smile Mile - Kids Run

Blue Jacket Park 14 Mar 2026

KIDS

The Great Duck Derby 2026

1300 S Denning Dr, Winter Park, FL 28 Mar 2026

SPORTS

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Upcoming Comedy Events

Dark Eighties Dance Party

Conduit 13 Feb 2026

USD 12

Free for Seniors: Solo Mio

Aloma Cinema Grill 10 Feb 2026

ENTERTAINMENT FREE

Free for Seniors: Solo Mio

Aloma Cinema Grill 9 Feb 2026

ENTERTAINMENT FREE

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Upcoming Galentines Day Events

Galentine’s with the Girls ✨

Penthouse 450 7 Feb 2026

GALENTINES-DAY FREE

Galentine’s Day: DIY Sugar Scrub Workshop

The Spa at The Alfond Inn 13 Feb 2026

WORKSHOPS USD 30

Galentines Wellness Event

Oakberry Acai 8 Feb 2026

HEALTH-WELLNESS FREE

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Upcoming Mardi Gras Events

Mardi Gras NOLA Nite - DJ, Dinner & Cocktails at Tibby's in Winter Park

Tibby's New Orleans Kitchen 13 Feb 2026

MARDI-GRAS FREE

Fat Tuesday Mardi Gras Block Party at Tibby's in Winter Park

Tibby's New Orleans Kitchen 17 Feb 2026

ENTERTAINMENT FREE

Dueling Pianos Mardi Gras Brunch at Tibby's New Orleans Kitchen Winter Park

Tibby's New Orleans Kitchen 15 Feb 2026

MARDI-GRAS FREE

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Upcoming Black History Month Events

The Rebel Run 5K Returns | Running Black History Forward

Martin Luther King, Jr. Park 7 Feb 2026

BLACK-HISTORY-MONTH USD 23 TO 39

Free Matinee for Seniors: Sarah’s Oil

Aloma Cinema Grill 5 Feb 2026

BLACK-HISTORY-MONTH FREE

Free Matinee for Seniors: Sweetwater

Aloma Cinema Grill 17 Feb 2026

ENTERTAINMENT FREE

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Upcoming Pop-Ups Events

OIFW Summer Shows: Winter Park Events Center (Multiple Shows 3pm & 7pm)

Winter Park Events Center 6 Jun 2026

FASHION USD 55 TO 71

Orlando Local Makers at Foxtail Coffee Winter Park!

Foxtail Coffee (Winter Park, FL) 1 Feb 2026

POP-UPS

Pop Up Infrared Heated Power

1740 SR-436 #128, Winter Park, FL, United States, Florida 32792 22 Feb 2026

POP-UPS

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Trending Events in Winter Park

Brookshire Carnival

2500 Cady Way, Winter Park, FL 28 Feb 2026

CARNIVALS

MamboYá Social - Super Bowl Edition w Tasha

The Trap 8 Feb 2026

SPORTS

SUPER BOWL SUNDAY Watch Party at Aloma Cinema Grill in Winter Park, FL!

Aloma Cinema Grill 8 Feb 2026

ENTERTAINMENT FREE

AdventHealth Winter Park Road Race 10k and 2 Mile

Park Avenue Central Park 28 Mar 2026

SPORTS

AdventHealth Run 4 Love 4 Mile

250 Perth Ln, Winter Park, FL 32792, United States 14 Feb 2026

SPORTS

Candlelight: Tribute to Bad Bunny | Orlando

Azalea Lodge at Mead Botanical Garden 6 Feb 2026

ENTERTAINMENT

Uada and Mortiis, with Special Guests Rome and Wraith Knight in Orlando

Conduit 3 May 2026

FREE

2026 Winter Park Fashion Week Show

Full Sail Live 21 Feb 2026

FASHION USD 150 TO 1,069

Candlelight: Tribute to Adele

Mead Botanical Garden 28 Jan 2026

CANDLELIGHT-CONCERTS

Rollins Summer Volleyball Camps 2026

Alfond Sports Center 11 May 2026

SPORTS USD 164 TO 487

Free Boat Tour: Sponsored by Charter Research

Scenic Boat Tour 24 Feb 2026

FREE

Love Your Library: Books & Boots

1052 W Morse Blvd, Winter Park, FL, United States, Florida 32789 7 Feb 2026

MUSIC

Cassadee Pope

Conduit 7 Mar 2026

CONTESTS

Fiddler's Green Charity 5K

Mead Botanical Garden 21 Feb 2026

NONPROFIT

Orlando Gay Chorus Presents: "Love Is...A Drag" Cabaret

Blue Bamboo Center For The Arts 21 Feb 2026

HEALTH-WELLNESS

More things to do in Winter Park