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Things to Do in Winter Park: Discover the Best Events, Attractions, and Activities

Are you searching for an array of engaging things to do in Winter Park? Immerse yourself in the city's rich culture, events, restaurants, tour historical landmarks, and partake in thrilling entertainment options. Whether you're a local or a tourist, Winter Park promises an ever-evolving and enjoyable array of activities!

Music

Some of our favorite Music events in Winter Park.

See all
$33.94
Multiple dates
Fri, Jun 05, 2026
6:00 PM

Rocking on the River w/ Megan Gunn Aboard the Barbara Lee

St Johns Rivership Co., 433 N Palmetto Ave, Sanford, FL 32771, United States
Sat, Jun 06, 2026
7:30 PM

Charlie Puth: Whatever's Clever! World Tour

Addition Financial Arena, 12777 Gemini Blvd N, Orlando, FL 32816, United States
$47.41
Sat, Jun 06, 2026
10:00 PM

Purple Moon | Pride Weekend Orlando

Fixtion, 15 N Orange Ave, Orlando, FL 32801, United States
Sun, Jun 14, 2026
7:30 PM

A$AP Rocky - Don't Be Dumb World Tour

Kia Center, 400 W Church St, Orlando, FL 32801, United States
Wed, Jun 17, 2026
8:00 PM

5 Seconds of Summer: EVERYONE'S A STAR! World Tour

Kia Center, 400 W Church St, Orlando, FL 32801, United States
Sat, Jun 20, 2026
8:00 PM

Orlando Sensation Fest

Kia Center, 400 W Church St, Orlando, FL 32801, United States
$64.58
Fri, Jul 03, 2026
10:00 PM

Mike Posner At The Vanguard

Vanguard, 578 N Orange Ave, Orlando, FL 32801, United States
$25.57
Sat, Jul 04, 2026
5:00 PM

2026 Official Orlando 4th of July Bar Crawl

Basement, 68 E Pine St, Orlando, FL 32801, United States
Thu, Jul 16, 2026
7:00 PM

Megan Moroney: The Cloud 9 Tour

Kia Center, 400 W Church St, Orlando, FL 32801, United States
Thu, Jul 23, 2026
7:00 PM

Louis Tomlinson - How Did We Get Here? World Tour

Addition Financial Arena, 12777 Gemini Blvd N, Orlando, FL 32816, United States
Sat, Jul 25, 2026
7:30 PM

Lionel Richie and Earth, Wind & Fire - Sing a Song All Night Long

Kia Center, 400 W Church St, Orlando, FL 32801, United States

Sports

Some of our favorite Sports events in Winter Park.

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Thu, Jun 04, 2026
7:00 AM

Doughnut Day 5k - VIRTUAL RACE

Virtual
Multiple dates
Fri, Jun 05, 2026
7:30 PM

Silver Spurs Rodeo

Osceola Heritage Park, 1875 Silver Spur Ln, Kissimmee, FL 34744, United States
Sat, Jun 06, 2026
5:00 PM

Orlando Pirates vs. Iowa Barnstormers

Kia Center, 400 W Church St, Orlando, FL 32801, United States
Thu, Jun 11, 2026
7:00 AM

World Cup Watch Party at FastBreak

Fastbreak, 6001 Destination Pkwy, Orlando, FL 32819, United States
Sun, Jun 21, 2026
7:30 PM

Orlando Pirates vs. Jacksonville Sharks

Kia Center, 400 W Church St, Orlando, FL 32801, United States
Sun, Jul 05, 2026
7:30 PM

Orlando Pirates vs. Green Bay Blizzard

Kia Center, 400 W Church St, Orlando, FL 32801, United States
$83.25
Sun, Jul 19, 2026
2:30 PM

"The Wharf" World Soccer Tournament Final Watch Party - July 19th

3274 Margaritaville Blvd, Kissimmee, FL 34747, United States
Sat, Jul 25, 2026
7:30 PM

Orlando City SC vs. Nashville SC

Inter&Co Stadium, 655 W Church St, Orlando, FL 32805, United States
Sat, Aug 15, 2026
7:30 PM

Orlando City SC vs. FC Cincinnati

Inter&Co Stadium, 655 W Church St, Orlando, FL 32805, United States
Wed, Aug 19, 2026
7:30 PM

Orlando City SC vs. Chicago Fire FC

Inter&Co Stadium, 655 W Church St, Orlando, FL 32805, United States
Sat, Sep 05, 2026
7:30 PM

Orlando City SC vs. San Diego FC

Inter&Co Stadium, 655 W Church St, Orlando, FL 32805, United States
Sat, Sep 12, 2026
7:30 PM

Orlando City SC vs. Toronto FC

Inter&Co Stadium, 655 W Church St, Orlando, FL 32805, United States

Art & Theatre

Some of our favorite Art & Theatre events in Winter Park.

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Multiple dates
Fri, Jun 05, 2026
5:00 PM

Blue Man Group

Icon Park, 8375 International Dr, Orlando, FL 32819, United States
$37.28
Fri, Jun 12, 2026
8:00 PM

Queers for Fears: A Pride Month Horror Burlesque Show

Me Theatre, 1300 La Quinta Dr, Orlando, FL 32809, United States
Free
Fri, Jul 10, 2026
10:00 AM

Winter Park Arts Festival

150 W Morse Blvd, Winter Park, FL 32789, United States
$144.02
Sun, Jul 12, 2026
3:00 PM

Miss Florida USA & Miss Florida Teen USA Finals

10000 International Dr, Orlando, FL 32819, United States
Fri, Jul 24, 2026
8:00 PM

Adam Ray: WHO IS ME Tour

Hard Rock Live, 6050 Universal Blvd, Orlando, FL 32819, United States
Fri, Aug 07, 2026
8:00 PM

Derek Hough - Symphony of Dance: Encore

Dr. Phillips Center for the Performing Arts, 445 S Magnolia Ave, Orlando, FL 32801, United States

Food & Drink

Some of our favorite Food & Drink events in Winter Park.

See all
Thu, Jun 04, 2026
8:00 AM

Bite 30

Orlando, FL, United States
Sat, Jun 06, 2026
10:00 AM

Baldwin Park Sunshine Market

4980 New Broad St, Orlando, FL 32814, United States
$286.07
Multiple dates
Sat, Jun 06, 2026
11:00 AM

International Food Fest: A World of Flavors

5771 N Apopka Vineland Rd, Orlando, FL 32818, United States
Sat, Jun 06, 2026
12:00 PM

Sip and Thrift

274 N Orange Ave, Orlando, FL 32801, United States
Sat, Jun 06, 2026
4:00 PM

Florida Vintage Fest

Great Southern Box Company, 2105 N Orange Blossom Trl, Orlando, FL 32804, United States
Sun, Jun 07, 2026
12:00 PM

Paint With All the Colors of Pride Market

1901 Chief Osceola Trl, Kissimmee, FL 34744, United States
$22.11
Sat, Jun 13, 2026
6:00 PM

Pride and Proud Pub Crawl

808 E Washington St, Orlando, FL 32801, United States
Sat, Jun 13, 2026
8:00 PM

Bop To The Top (18+)

House of Blues, 1490 E Buena Vista Dr, Orlando, FL 32830, United States
Fri, Jun 26, 2026
2:00 PM

Mini Mercado

Ivanhoe Park Lager House, 23 N Orange Blossom Trl, Orlando, FL 32805, United States
Sat, Jun 27, 2026
7:30 PM

Saved By The 90's

House of Blues, 1490 E Buena Vista Dr, Orlando, FL 32830, United States
Sun, Jun 28, 2026
1:00 PM

Summerween Market

The Great Southern Box Company, 2105 N Orange Blossom Trl, Orlando, FL 32804, United States

Seasonal & Holiday

Some of our favorite Seasonal & Holiday events in Winter Park.

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Free
Sat, Jul 04, 2026
11:00 AM

Sunset Walk Orlando - Kids' 4th of July Family Celebration

Promenade at Sunset Walk, 3251 Margaritaville Blvd, Kissimmee, FL 34747, United States
$25.57
Sat, Jul 04, 2026
5:00 PM

2026 Official Orlando 4th of July Bar Crawl

Basement, 68 E Pine St, Orlando, FL 32801, United States
$20.00
Tue, Jun 09, 2026
8:30 PM

Duck and Goose Late Hour (at the SBC Annual Meeting)

American Social Bar & Kitchen, 7335 W Sand Lake Rd, Orlando, FL 32819, United States
$81.88
Thu, Jun 11, 2026
11:00 AM

THE TOURISM IMPACT INITIATIVE – CENTRAL FLORIDA | Kick-Off Summit 2026

Sixty Vines, 7760 W Sand Lake Rd, Orlando, FL 32819, United States
$229.25
Sat, Jun 13, 2026
3:00 PM

Father's Day Kickback Party

Napasorn Thai Restaurant, 56 E Pine St, Orlando, FL 32801, United States
$161.90
Sun, Jun 14, 2026
10:00 AM

Cruise With CassLav

Port Canaveral, Cape Canaveral, FL, United States
Free
Mon, Jun 15, 2026
11:00 AM

KLT Travel Magical Meet Ups

Disney's Hollywood Studios, 351 Studio Dr S, Orlando, FL 32830, United States
Free
Wed, Jun 17, 2026
3:00 PM

Journey Your Way: A World of Travel for Every Traveler

Roseborough Travel Agency, 610 E New York Ave, DeLand, FL 32724, United States
Free
Thu, Jun 18, 2026
11:00 AM

Orlando Birthday Celebration

Orlando Family Physicians, 1130 Semoran Blvd S, Orlando, FL 32807, United States
Free
Thu, Jun 18, 2026
2:00 PM

AAA Presents Celebrity Cruises

955 Bichara Blvd, Lady Lake, FL 32159, United States
$172.42
Fri, Jun 19, 2026
6:00 PM

UNITY Juneteenth Block Party Powered by T.Gaines Ent

274 N Orange Ave, Orlando, FL 32801, United States
$23.18
Sat, Jun 20, 2026
12:30 PM

Family Clay Party at Songbirds- Frog in Boots

Songbirds Music Art & Dance Center, 181 E Mitchell Hammock Rd, Oviedo, FL 32765, United States

Health & Wellness

Some of our favorite Health & Wellness events in Winter Park.

See all
$15.00
Multiple dates
Sat, Jun 06, 2026
8:50 AM

Yoga in the Garden

1300 S Denning Dr, Winter Park, FL 32789, United States
$10.00
Thu, Jun 04, 2026
1:00 PM

Pop-Up Park Picnic: Couple Date Night (Self-Guided) - Casselberry Area!

Wirz Park, Mark David Blvd, Casselberry, FL 32707, United States
$171.50
Thu, Jun 04, 2026
10:00 AM

Pastors & Leaders Conference 2026

Church in the Son, 4484 N John Young Pkwy, Orlando, FL 32808, United States
$57.92
Fri, Jun 05, 2026
5:00 AM

Friday Reset

El Coqui Bakery, 512 Sanford Ave, Sanford, FL 32771, United States
$28.52
Fri, Jun 05, 2026
7:00 AM

Chakras: An Overview & Reset of Your Inner Centers

The Urban Ashram, 310 E New Hampshire St, Orlando, FL 32804, United States
Free
Fri, Jun 05, 2026
9:00 AM

Instore Yoga With Ignite your Flow

1668 E Buena Vista Dr, Orlando, FL 32830, United States
Free
Fri, Jun 05, 2026
1:00 PM

2026 Florida Regional ECK Soul Adventure Weekend

Marriott, 1501 International Pkwy, Lake Mary, FL 32746, United States
$49.87
Fri, Jun 05, 2026
6:30 PM

Floating Sound Bath with Jirod

Zaharias Dr, Orlando, FL 32837, United States
$79.57
Fri, Jun 05, 2026
6:30 PM

ALW - Atomic Games

Holiday Inn Melbourne-Viera Conference Ctr, 8298 N Wickham Rd, Melbourne, FL 32940, United States
$25.00
Fri, Jun 05, 2026
7:00 PM

✨ CHAKRAS: An Overview & Reset of Your Inner Centers✨

The Urban Ashram, 310 E New Hampshire St, Orlando, FL 32804, United States
Free
Sat, Jun 06, 2026
7:30 AM

YogaSix Day

Yogasix Viera, 7954 N Wickham Rd, Melbourne, FL 32940, United States

Education & Networking

Some of our favorite Education & Networking events in Winter Park.

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Free
Thu, Jun 04, 2026
8:00 AM

LAUNCH SUMMER CAMP: SPACE WEEK

Launch Entertainment Park, 610 Alafaya Trl N, Orlando, FL 32828, United States
$375.32
Multiple dates
Mon, Jul 06, 2026
9:00 AM

Leu Gardens Discovery Camp - Rainforest Week

Harry P. Leu Gardens, 1920 N Forest Ave, Orlando, FL 32803, United States
$189.47
Thu, Jun 04, 2026
9:00 AM

Center Stage Princess Camp

Center Stage Dance and Performing Arts, 520 Wayne Ave, New Smyrna Beach, FL 32168, United States
$108.55
Thu, Jun 04, 2026
9:00 AM

ACA Summer Teen Art Camp - Week ONE June 2-5, 2026

123 Douglas St, New Smyrna Beach, FL 32168, United States
$188.58
Thu, Jun 04, 2026
9:00 AM

ACA Summer Art Camp - Week ONE June 2-5, 2026

Atlantic Center for the Arts, 1414 Art Center Ave, New Smyrna Beach, FL 32168, United States
$31.95
Thu, Jun 04, 2026
7:30 PM

Unwind Orlando-Networking Hangout

Bar Louie, 7015 S Semoran Blvd, Orlando, FL 32822, United States
$50.29
Fri, Jun 05, 2026
9:00 AM

The Orlando Brew Crew

235 S Central Ave, Oviedo, FL 32765, United States
$1065.71
Fri, Jun 05, 2026
10:00 AM

Momentum Retreat 2026

Clawson Way, Kissimmee, FL 34747, United States
Free
Fri, Jun 05, 2026
10:30 AM

Broker Open + Special Class: How to Read a Closing Disclosure

15026 Summer Harvest St, Winter Garden, FL 34787, United States
Free
Fri, Jun 05, 2026
5:00 PM

June Night of Networking | Caribbean American Chamber of Commerce, Inc.

Orlando Fashion Square-North, 3201 E Colonial Dr, Orlando, FL 32803, United States
Free
Fri, Jun 05, 2026
6:00 PM

Right way to wholesale real estate

875 Woodbury Rd, Orlando, FL 32828, United States
Free
Fri, Jun 05, 2026
6:00 PM

Tax-Deferred Real Estate Strategies for Dentists

Charley's Steak House, 2901 Parkway Blvd, Kissimmee, FL 34747, United States

Travel

Some of our favorite Travel events in Winter Park.

See all
$10.00
Thu, Jun 04, 2026
1:00 PM

Pop-Up Park Picnic: Couple Date Night (Self-Guided) - Casselberry Area!

Wirz Park, Mark David Blvd, Casselberry, FL 32707, United States
$65.00
Multiple dates
Fri, Jun 05, 2026
11:00 AM

Winter Park Mystery Picnic: Self-Guided Foodie Adventure

Downtown Orlando, Orlando, FL, United States
Free
Sat, Jun 06, 2026
8:00 AM

Paddleboard Cleanup at Lake Killarney

Beachview Ave, Winter Park, FL 32789, United States
$81.88
Multiple dates
Sat, Jun 06, 2026
9:00 AM

Basic Handgun Training: A class that trains you to defend your life

3812 Cypress Gardens Rd, Winter Haven, FL 33884, United States
$137.84
Sat, Jun 06, 2026
6:30 PM

Paris Beneath the Stars: Picnic & Friendship Night

Gallery J, 920 Belle Ave, Winter Springs, FL 32708, United States
Free
Wed, Jun 10, 2026
7:00 PM

Orlando Sentinel's 150th Anniversary, Beer Release and Weather Discussion

Ten10 Brewing, 1010 Virginia Dr, Orlando, FL 32803, United States
Free
Thu, Jun 11, 2026
10:30 AM

Estuary Exploration

Sleepy Hollow Rd, New Smyrna Beach, FL 32168, United States
$81.88
Thu, Jun 11, 2026
11:00 AM

THE TOURISM IMPACT INITIATIVE – CENTRAL FLORIDA | Kick-Off Summit 2026

Sixty Vines, 7760 W Sand Lake Rd, Orlando, FL 32819, United States
$31.74
Thu, Jun 11, 2026
2:00 PM

Dave & Buster's - Orlando

Dave & Busters, 8986 International Dr, Orlando, FL 32819, United States

Lifestyle

Some of our favorite Lifestyle events in Winter Park.

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$75.00
Sat, Jun 06, 2026
11:30 AM

Bonsai & Cheers -Home State Brewing - L&J Nursery - Dwarf Jade Bonsai

Home State Brewing Co, 16016 New Independence Pkwy, Winter Garden, FL 34787, United States
$2000.00
Multiple dates
Sat, Jun 27, 2026
6:00 PM

Speak With Pride 2026

255 S Orange Ave, Orlando, FL 32801, United States
$171.50
Thu, Jun 04, 2026
10:00 AM

Pastors & Leaders Conference 2026

Church in the Son, 4484 N John Young Pkwy, Orlando, FL 32808, United States
$321.58
Thu, Jun 04, 2026
10:00 AM

GIW Orlando / Passes June 4–8, 2026 Girls in Wonderland

Towneplace Suites, 13295 Hartzog Rd, Winter Garden, FL 34787, United States
$51.94
Thu, Jun 04, 2026
1:00 PM

GIW aka Girls in Wonderland- Orlando 2026 - Tickets Only

Towneplace Suites, 13295 Hartzog Rd, Winter Garden, FL 34787, United States
$41.74
Thu, Jun 04, 2026
7:30 PM

Game Night- Orlando

6935 Lake Ellenor Dr, Orlando, FL 32809, United States
Free
Fri, Jun 05, 2026
10:00 AM

Men's Day at One Senior Place

Senior Partner Care Services, 8085 Spyglass Hill Rd, Melbourne, FL 32940, United States
$49.87
Fri, Jun 05, 2026
1:00 PM

Watercolor: Hummingbird and Hibiscus

Harry P. Leu Gardens, 1920 N Forest Ave, Orlando, FL 32803, United States
$106.00
Fri, Jun 05, 2026
1:00 PM

Cutting Boards with Juice Grooves & Handles

Rockler Woodworking & Hardware, 515 E Altamonte Dr, Altamonte Springs, FL 32701, United States
Free
Fri, Jun 05, 2026
3:00 PM

***OPEN HOUSE*** DESCUBRE TU PROXIMO HOGAR EN ST CLOUD

14 Sunset Haven Loop, St Cloud, FL 34771, United States

Nearby Cities

Check out these cities near you.

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Alafaya, FL

Altamonte Springs, FL

Apopka, FL

Azalea Park, FL

Buenaventura Lakes, FL

Casselberry, FL

Celebration, FL

Clermont, FL

Conway, FL

Daytona Beach, FL

DeBary, FL

DeLand, FL

Deltona, FL