Calendar and Family Calendar



Running of the Chihuahuas

Cocina 214 will host its fourth annual Running of the Chihuahuas beginning at 11 a.m. on Sunday, May 1.


Night On Broadway at WPHS

For over 15 years, Night On Broadway has been a highlight of the artistic year for Winter Park High School and the Winter Park community.


JM 24 Fun Run

From 10 a.m. to 1 p.m. on April 16 Trinity Preparatory School will host the JM 24 Fun Run. The school is at located at 5700 Trinity Prep Lane in Winter Park.


Earth Day in the Park

Earth Day in the Park will be hosted on Sunday, April 10, from 11 a.m. to 3 p.m. in Central Park.


Doggie Art Festival

Come out on Sunday, April 3, for one of Winter Park’s most beloved events, the 13th annual Doggie Art Festival!


Winter Park Easter Egg Hunt

The 62nd annual Winter Park Easter Egg Hunt will begin at 10 a.m. on Saturday, March 26.

Tease photo

Easter Lice Egg Hunt?

Stopping lice

This year there is a new type of "egg hunt" you'll want your family participating in: a hunt for lice and lice eggs.


Winter Park Sidewalk Art Festival

The 57th annual Winter Park Sidewalk Art Festival will be held Friday, March 18, through Sunday, March 20, in Central Park and on Park Avenue.


Get Your Jazz On

Enjoy jazz under the stars at the Alfond Inn on Friday, March 11 from 6:30 to 9:30 p.m.

Tease photo

Taste of Oviedo this weekend!

Food event returns

Taste of Oviedo has over 30 food vendors participating, and has added a larger seating area geared towards our local Oviedo restaurants.


Fiddler’s Green 5K

The eighth annual Fiddler’s Green 5K is a fun run/walk hosted by Fiddler’s Green Irish Pub on Saturday, March 5.


Fourth Friday Food Truck Event

The Maitland Civic Center will host its monthly Fourth Friday Food Truck Event on Friday, Feb. 26, from 6 to 9 p.m.


Woman’s Show of Winter Park

From 9 a.m. to 4 p.m., the Woman’s Show of Winter Park will include over 20 vendors selling jewelry, candles, boutique items, spa and beauty products, art, fashion and purses.


Run 4 Love 4 Mile

Florida Hospital presents Run 4 Love 4 Mile on Feb. 13 at 7:30 a.m., benefiting the Track Shack Foundation.


Valentine's concert in Winter Park

Enjoy an afternoon of music and romance with Michael Andrew and Swingerhead at the main stage in beautiful Central Park in downtown Winter Park from 2:30 to 5 p.m. on Sunday, Feb. 7.