Winter Park Events & Things to Do

Join Your Caring Law Firm and friends for our Downton Abbey party!

Join us for Winter Park Wine Down! All you can drink wine, sangria & draft Tecate light and ALL YOU CAN EAT TACOS for $15

This is one of the oldest Farmer's Markets in the country. it's a real experience and a great way to spend a Saturday morning.

We're kicking off Oktoberfest with a fun, in-store event! We'll have a demos hosted by Big Storm Brewing Co. and beer cheese and pretzel stations.

Celebrate Smithsonian Magazine’s Museum Day with a special highlights tour inspired by the 2019 theme: Smithsonian Year of Music.

This lecture examines the legacy of American abstract artists George L.K. Morris and Suzy Frelinghuysen.

Join us on Tuesday, September 24th from 5pm-10pm for our monthly wine, cheese and chocolate event! Enjoy three tastings of decadent chocolate and cheeses with wine pairings. $25 per person. Reservations required. Call to reserve: 407-636-7022

Join us at the Cornell Fine Arts Museum every third Thursday of the month as we reflect on the past while delving into various historical works on view. Each Throwback Thursday Tour explores new works and themes.

In celebration of Hispanic Heritage Month, this tour with Curator Gisela Carbonell will explore works by Latin American and Latinx artists in the collection.

Join Curator Gisela Carbonell for tours in Spanish. These tours are for everyone – whether you currently speak Spanish or wish to brush up on your language skills.

Walking on the lap of the Great Himalayas with the crystal clear view of majestic mountains just in front of your eyes is possible only in the Everest Region. Everest base camp trek is the most awe-inspiring popular trekking trail of Nepal in the world.

Join the Cornell Fine Arts Museum on the first Wednesday of each month for a tour of the Alfond Collection of Contemporary Art, on view at The Alfond Inn in Winter Park.

Super SOLE Saturdays are gonna get us through 2019! Come relax, chat, and learn some fun stuff!

Join us at the museum for an evening of live music, presented by Ugly Orange.

Come join us for an amazing evening out in beautiful Winter Park featuring unlimited tastings from 40 of Orlando's top food and drink options + live music inside & outside. A percentage of proceeds to benefit Caring By Sharing United a 501(c)(3) nonprofit organization

To register: run to https://www.trackshack.com/event/10352 Enjoy photo ops and candy stops along the route. Finish with bounce houses, cold treats, face painters and trick or treating!

The Winter Park Chamber of Commerce is proud to host the festival on the second weekend in October each year. The community-oriented sidewalk show presents quality visual art and live entertainment the whole family can enjoy.

The Boss Babes Brunch Tour is the premier networking and empowerment event for women in business who are looking to Boss Up and take their brands to the next level. This event is for women of all backgrounds and levels.

Backyard Biodiversity Day (BBD) was created to celebrate diversity in the landscape. We invite you to spend a day with us, teaching about native plants, pollinators, wildlife, and why they are important.

Join Smithsonian American Art Museum’s Curator Virginia Mecklenburg for an in-depth look into the diverse perspectives that make up the American story as reflected by the broad selection of works in this exhibition.

Almost 60 years ago, George Kubler’s book The Shape of Time challenged the accepted art historical narrative by suggesting that art is simply the visual manifestation of a continuous conversation through time.

Join us for a night of music, dance, and fundraising as Love Your Life Foundation and Personal Power and Prosperity co-host our first Halloween Masquerade Party! All proceeds from this event go to support the 2020 P3 Kids Course.

Join the party! We're throwin' a 10-year birthday bash at 4 Rivers Smokehouse on Saturday, Oct. 26, just down the road from where it all started back in 2009.

Join us for our second annual Spooky Halloween Wine Down at Winter Park! Featuring an all you can eat taco bar and all you can drink wine, sangria and draft Tecate Light

This year, the Cornell Fine Arts Museum will participate in The City of Winter Park’s Pumpkins & Munchkins event in Shady Park at Hannibal Square.

A selection of “verses” or segments from Jennifer Crandall’s Emmy nominated film Whitman Alabama will be screened followed by a lecture and discussion with Ben Hudson, Associate Professor of English at Rollins.

The Maitland Rotary Art Festival has been entertaining Central Florida residents and visitors since 1976. Although hosted annually by the Rotary Club of Maitland, Florida, the event has evolved into a community celebration of the arts.

The 8th Annual Cows 'n Cabs charity fundraising event features mini-dish tastings from 25+ gourmet Orlando restaurants paired with over 200 wines and a plethora of craft beers and cocktails.

Drop by for fun activities perfect for the whole family, including a scavenger hunt in the galleries and hands-on art making connected to the exhibitions on view. All materials are provided. Free and open to the public.

Join Curator Gisela Carbonell for tours in Spanish. These tours are for everyone – whether you currently speak Spanish or wish to brush up on your language skills.

The Crazy Wine Dash is a 5K Run with the craziest amounts of wine and fun out there! The race starts and finishes in some of the best venues across the country.

Join us at our table and enjoy a chef-inspired Thanksgiving Feast at The Alfond Inn.

Join Curator Gisela Carbonell for tours in Spanish. These tours are for everyone – whether you currently speak Spanish or wish to brush up on your language skills.

Join us at the Cornell Fine Arts Museum every third Thursday of the month as we reflect on the past while delving into various historical works on view. Each Throwback Thursday Tour explores new works and themes.

Join us to bring in 2019 with style - Orlando's most affordable New Years Eve Party is also the most fun & classy happening at the Alfond Inn's Lounge.

It's our 5th year and we will be packing out the haven 1 more time before expanding!! 3 days! Bands RVNT KILL THE IMPOSTER CATCHER AND THE RYE DEMONFUCK

Sunday 1:00 p.m. Alfond Inn Tour

Saturday 1:00 p.m. Highlights Tour

Join Orlando’s Best Kentucky Derby Experience Winter Park Style! Enjoy 4-hours of all the fun you can have at the ultimate Kentucky Derby viewing experience with unlimited food, premium open bars, TV's & music inside & outside.

Indoor skiing and snowboarding is now available in Orlando and central Florida all year round. Our state of the art Ski center features two indoor ski slopes plus an interactive panoramic ski simulator.