9th annual Chili for Charity


The 9th annual Chili for Charity is the premiere chili cook-off event in central Florida! The event features creative chili dishes by popular local and favorite restaurants in the central Florida area.
Participants will have their dishes evaluated by a select panel of judges and compete for the coveted Peoples’ Choice award. Guests will enjoy all types of chili, drinks, live entertainment and networking while enjoying the beautiful Winter Park Farmers’ Market.

A bountiful silent auction will close out the evening and event proceeds will benefit the Rotary Club of Winter Park Charitable Foundation, which provides grants to more than 30 local charities annually. Over the last 20 years, the club has donated more than $800,000+ to non-profit organizations serving the Winter Park community.


Date : Feb.26,2020 from 5:30pm to 9pm

Event location : Winter Park Farmers’ Market – 200 W. New England Ave.
Winter Park, FL 32789 United States

Contact : Phone contact: 503-807-8669 – Website: http://www.biddingforgood.com/RCWP

Park Avenue Sidewalk Sale



Shop till you drop at the January Sidewalk Sale along beautiful Park Avenue. Enjoy savings from 50 – 75% off, at participating retailers. Retail hours vary by location.



Date : Feb.23-26, 2020

Event location : Park Avenue, Winter Park

Contact : Must call for times: 407-644-8281

12th annual Fiddler’s Green 5K


The 12th annual Fiddler’s 5K race is a fun run/walk that will raise money for local charities. For those who may think running is overrated there will be a Pint .5k (that’s 1,640 feet) ending with a glass full of beer at Fiddler’s Green.
The race will begin at 7:30 a.m. in Mead Garden, run through beautiful Winter Park, and return to Mead Garden.

There will be an award presentation at 8:45 a.m. From there, the runners, walkers, pups and their cheering squads are invited back for beer and fun at Fiddler’s Green Irish Pub.

Rate: $25 – $35


Date : Feb.22,2020 at 7:30am

Event location : Mead Botanical Garden – 1300 S. Denning Dr. Winter Park, FL 32789 United States

Contact : Phone contact: 321-662-6182 – Website: http://fiddsgives.org/

Contemporary Sculpture Garden Tour


A must see exhibit on the picturesque grounds of Crealdé School of Art’s main campus. 60 three-dimensional pieces of outdoor art made of forged metal, cast bronze, concrete and more. The lakeside Contemporary Sculpture Garden is open to the public. Lynn Brenner-Katz, Crealdé Sculpture Instructor, takes you on a fascinating tour through the beautifully landscaped campus, revealing the abundant diversity of expressive styles, durable media, and fun facts about the various inspired sculptors who created these works of art. Special discount coupons for Crealdé spring classes will be available at the event.

This special event is part of the City of Winter Park’s Weekend of the Arts.


Date : Feb.15, 2020 from 10:30am to 11:30am

Event location : Crealdé School of Art – 600 Saint Andrews Blvd.
Winter Park, FL 32792 United States

Contact : Phone contact: 407-671-1886 – Website: http://crealde.org/

Christmas Day!


Many Canadians have a day off work on December 25 and many spend the day with close relatives or friends. It is customary to exchange gifts, enjoy a special festive meal and, perhaps, attend a special church service.

In some Canadian families and in the United States, a mythical figure called Santa Claus brings gifts. He travels on a sleigh pulled by reindeer, enters homes via the chimney and leaves presents and candy in Christmas stockings or in a pile under the Christmas tree. In other families, individual members exchange carefully selected gifts. Popular gifts are toys, games and candy for children and clothes, music, alcohol and practical or luxury items for adults. Canadians may open their presents on Christmas Eve after a special church service or during the morning or after lunch on Christmas Day.

The original meaning of Christmas is a special church service, or mass, to celebrate the birth of Christ. The story of the Nativity, or the events surrounding the birth of Jesus, are particularly important in religious celebrations of Christmas. However, many traditions that are around today have their roots in pre-Christian winter festivals. These include the importance of candles and decorations made from evergreen bushes and tree, symbolizing everlasting light and life.


Date :
December 25, 2019

Sip, Shop, Stroll


Experience the charm of Park Avenue on this uniquely Winter Park wine walk.

Spend the evening visiting your favorite Park Avenue area shops and restaurants. Discover new merchants, check out the latest fashions, gift ideas and seasonal menu items and enjoy wine and hors d’oeuvres along the way.

Our holiday season Sip, Shop and Stroll promises to be an even more festive wine walk than usual.

*Check-in is on the corner of Morse Boulevard and Park Avenue*

Fee: $25.


Date :
Thursday, December 12, 2019 | 5-8pm

Event location :
Begins at the corner of Morse Boulevard and Park Avenue
Park Avenue
Winter Park, FL 32789

Contact :
Tiffany Cahill at tcahill@winterpark.org

Website: https://winterpark.org/events/details/sip-shop-stroll-5036000

21st Annual Pancake Breakfast


Before and during the parade, Leadership Winter Park hosts its annual Pancake Breakfast at the Central Park stage from 7:00-10:30 a.m. Tickets cost $5 and include pancakes, sausage, coffee, milk, juice and fabulous toppings! Event proceeds benefit adult and youth leadership development programs. In addition, a portion of proceeds will benefit A Gift For Teaching which directly impacts students in our community.

Please click here to buy tickets.


Date :
Saturday, December 7, 2019 from 7 to 10:30am

Event location :
Central Park main stage
Park Avenue & Garfield Avenue
Winter Park, FL 32789 United States

Contact :
Amie Morgan at amorgan@winterpark.org

Website: https://winterpark.org/events/details/leadership-winter-park-pancake-breakfast-5036002

67th Annual Winter Park Christmas Parade


The Winter Park Chamber of Commerce is proud to host the 67th annual Winter Park “Ye Olde Hometown” Christmas Parade. The event has been held each December for more than 60 years, making it the oldest continuous holiday parade in Central Florida.

Each year the parade travels down Park Avenue, starting at Cole Avenue and proceeding south, ending at Lyman Avenue. More than 80 organizations participate including marching bands, local police and fire departments, scouting groups, local dignitaries and, of course, Santa Claus.


Date :
Saturday, December 7, 2019 from 9am to 10:30am

Event location :
Park Avenue
Winter Park, FL 32789

Contact :
Tiffany Cahill at tcahill@winterpark.org

Popcorn Flicks in the Park


This film is a part of our Popcorn Flicks series, which takes place in Central Park, Winter Park once a month and it’s FREE and open to the public!

Presented by Winter Park CRA and produced by Enzian Theater. This film series features classic films for the whole family.

This film is preceded by How The Grinch Stole Christmas (1966):

Inside a snowflake exists the magical land of Whoville, where the Whos live. All the Whos love Christmas, yet just outside of their beloved Whoville lives the Grinch, a nasty creature that hates Christmas, and plots to steal it away from the Whos, which he equally abhors. Yet a small child, Cindy Lou Who, decides to try befriend the Grinch. When he tries to wipe out Christmas for the cheerful Who-villians, the Grinch discovers that maybe Christmas doesn’t come from a store. Maybe Christmas perhaps means a little bit more! Magnificently narrated by Boris Karloff and animated by cartoon legend Chuck Jones, it’s an award-winning Who-roast-beast-feast of a holiday classic!


Buddy (Will Ferrell) was accidentally transported to the North Pole as a toddler and raised to adulthood among Santa’s elves. Unable to shake the feeling that he doesn’t fit in, the adult Buddy travels to New York, in full elf uniform, in search of his real father. As it happens, this is Walter Hobbs (James Caan), a cynical businessman. After a DNA test proves this, Walter reluctantly attempts to start a relationship with the childlike Buddy with increasingly chaotic results.

We encourage you to bring a blanket, a picnic or snacks, and some family and friends and join us. Free popcorn for everyone!

This month’s Popcorn Flicks in the Park is in conjunction with our annual Winter on the Avenue festivities. 


Date :
Friday, December 6, 2019 at 7pm

Event location :
Central Park main stage
Park Avenue & Garfield Avenue
Winter Park, FL 32789 United States

Contact :
Phone contact: 407-629-0054

Website: https://enzian.org/film/wall-e/

You’re a good Man, Charlie Brown


Charles Schulz’s beloved comic strip comes to life in this joyful, classic Broadway musical.  It’s an “average day in the life” of the Peanuts gang, from bright uncertain mornings to hopeful starlit evenings.  Blockhead Charlie Brown, bossy Lucy, prodigy Schroeder, perfectionist Sally, blanket-toting Linus and lovable Snoopy battle with kites, school, baseball and misunderstandings before finally realizing what makes them truly happy.

Week 11/14 – Thurs @ 7:30 p.m., Fri & Sat @ 2 & 7:30 p.m.
Week 11/21 – Thurs @ 2 p.m., Fri & Sat @ 2 & 7:30 p.m., Sun @ 2 p.m.
Week 12/5 – Thurs @ 2 p.m., Fri & Sat @ 2 & 7:30 p.m., Sun @ 2 p.m.
Week 12/12 – Thurs @ 2 p.m., Fri @ 7:30 p.m., Sat @ 2 & 7:30 p.m., Sun @ 2 p.m.

$45 Evening
$42 Senior Evening (62 and over)
$36 Matinee
$20 Industry (Entertainment Professional)
$20 Student (11-25 years old)*
*Students must be at least 11 years old to be admitted to a Mainstage performance.
Special Rates:
$20 Thursday Night & Friday Matinee preview (Opening Week)
$1 off groups of 10 or more (for regularly priced tickets)

The Winter Park Playhouse is Central Florida’s professional musical theatre and affiliated with Actors’ Equity Association.


Rate: $20 – $45.


Date :
Thursday, December 5, 2019

Event location :
711 Orange Avenue Suite C
Winter Park, FL 32789

Contact :
Phone contact: 407-645-0145

Website: https://app.arts-people.com/index.php?show=95391