- December 19, 2025
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MARCH 19
Kick off art festival weekend and celebrate the fine art of wine at the Hannibal Square Wine Tasting! Join the Winter Park Chamber of Commerce and the Hannibal Square Merchants Association on Thursday, March 19, for a fun evening of wine, food, music and friends. The event runs from 5 to 7:30 p.m. Tickets are $25 in advance, and $30 at the door. For more information, visit winterpark.org/content/hannibal-square-wine-tasting
MARCH 20
A 50-year anniversary celebration of The Venue on the Lake-Maitland Civic Center kicks off with a Fab and Funky Dance Party at 7 p.m. on Friday, March 20. The event will include live music from The Buzzcatz and the Maitland Stage Band. Light hors d'oeuvres, wine and beer will be served. Admission is $19.65, with reserved VIP packages costing $50. Call 407-647-2111.
The Winter Park Sidewalk Art Festival is one of the nation’s most prestigious outdoor art festivals. Each year more than 350,000 visitors enjoy the show. Festival hours are as follows: Friday, March 20, from 9 a.m. to 6 p.m.; Saturday, March 21, from 9 a.m. to 6 p.m. and Sunday, March 22, from 9 a.m. to 5 p.m. Expect to see dazzling sculpture and glass for the big pocketbook as well as smaller works to please just about anyone. Enjoy Friday night’s jazz concert, children’s workshop village and school art exhibits, and great food and sidewalk cafes. Visit cityofwinterpark.org for more information.
The Winter Park History Museum presents three pop-up exhibitions featuring the life of Mister Rogers. The exhibition celebrates the fascinating life of Fred Rogers beginning with his student days at Rollins College and later, his influence on millions of children through his television show. The Museum will host a two-day birthday party for Mister Rogers from 10 a.m. 4 p.m. on March 20 and 21. Visit wphistory.org for more information.
MARCH 22
Come out to the Winter Park Golf Country Club on Sunday, March 22, from 3 to 6 p.m. for a Fish Tales and Cocktails fundraising event to support Casting for Recovery, an organization that provides healing fishing retreats to breast cancer survivors. The event will include silent auctions, raffles, appetizers, a cash bar and a drawing for a 17-foot custom Gheenoe boat and trailer. Cost is $25. Visit castingforrecovery.org
MARCH 25
As family caregiving becomes more common for the aging population, many adult children and their parents find themselves unprepared for the costs and challenges of long-term care. To address planning concerns, One Senior Place, a resource center in Altamonte Springs, will host a panel discussion for seniors and caregivers on Wednesday, March 25, titled “Understanding Your Long Term Care Plan.” The program will help dispel the myths and misinformation surrounding long-term care, and answer questions about existing policies and care plans. Local professionals will participate in the open forum beginning at 9:30 a.m. at the senior resource center in Altamonte Springs. RSVPs are required for the March 25 event. For more information, contact One Senior Place at 407-949-6733.
MARCH 27
The Christian Service Center is taking a swing to knock out hunger on Friday, March 27, at 8:30 a.m. with their inaugural golf tournament at the historic Dubsdread golf course in downtown Orlando. The Take a Swing against Hunger Golf tournament is designed for the benefit of the Center’s neighbors in the Parramore district who are struggling with hunger, homelessness, or other similar crises. Christian Service Center for Central Florida is a nonprofit organization that seeks to mobilize the Central Florida community under one common mission to eradicate poverty through the provision of services and resources that foster hope, well-being and empowerment. Registration starts at 7 a.m. Call the center at 407-425-2523, ext. 230, or visit christianservicecenter.org
On Friday, March 27, the Goldenrod Historical Society will welcome Frank Attwood to the Goldenrod Station for a rendition of his famous Thomas Edison re-enactment. The event will begin at 7 p.m. and Mr. Edison's favorite apple pie will be served. Contact the Goldenrod Historical Society offices at 407-677-5980.
Learn more about Alzheimer’s and related dementias as Jerry Hamilton hosts a presentation on “How to Communicate When Logic Doesn’t Work” from 9:30 to 11:30 a.m. on Friday, March 27 at Arbor Village, located at 490 S. Old Wire Road in Wildwood. Registration is at 9 a.m. For more information and to RSVP, call Cindi at 407-843-1910.
MARCH 28
The sixth annual Hannibal Square Heritage Center Folk & Urban Art Festival will be Saturday, March 28, from 10 a.m. to 4 p.m. at the Hannibal Square Heritage Center. The annual festival celebrates the works of more than 25 artists, including members of the original Florida Highwaymen and the B-Side Artists collective. A highlight will be the creation of a lifecast by exhibiting Crealdé artist Riboberto Torres of Richard Hall, Hannibal Square hero and Tuskegee Airman. Featured music will include the Porchdogs Cajun and Zydeco Band and Orisi Risi African Folklore. A “kid-folk” workshop will offer “The Aztec Encounter and Musical parade.” Food truck fare will also be available.
MARCH 29
Sunday March 29 is Be My Neighbor Day in Winter Park. The Winter Park History Museum presents this fun event honoring the life of Mister Rogers. Activities for children ages 2 to 6 years old will include crafts, family entertainment and a special meet and greet with Daniel Tiger. The event will run from noon to 3 p.m. in Central Park. Visit wphistory.org for more information.
APRIL 11
Spring has sprung in the city of Winter Park and now is your chance to stop and smell the roses. On Saturday, April 11, at 9 a.m., the city’s Parks and Recreation Department’s Landscape Division will host its first Park Avenue Garden Tour. Catch an intimate glimpse into Park Avenue’s eye-catching planters, topiaries, hanging baskets and more with a city horticulture specialist on this flowery, two-block tour. Attendees will learn about plants fit for a Florida garden, which include over 30 species featuring different shapes, sizes, textures and fragrances. The one-hour morning tour begins at Garfield Avenue (behind the Central Park main stage), continues through the meandering sidewalks in Central Park, and reaches its final destination at the blooming Central Park Rose Garden. Free public parking is available on-street or on the fourth and fifth floors of the Park Place parking garage at Park and Canton avenues. If you’re looking for gardening inspiration, green thumb tips, or a refreshing activity to do after visiting the Winter Park Farmers Market, be sure to reserve a spot on the tour. Space is limited. Please RSVP by Friday, April 3, to 407-599-3397.
APRIL 12
Enjoy an Ice Cream Social to benefit Ronald McDonald House Charities of Central Florida from 1 to 5 p.m. on Sunday, April 12, at the Winter Park Civic Center, located at 1050 W. Morse Blvd. in Winter Park. Cost is $6 in advance and $8 at the door. Tickets are available at both Ronald McDonald Houses and from the Friends of RMHCCF Steering Committee. Call 407-677-1552 or visit rmhorlando.org/events
APRIL 18
Honor local veterans from 9 a.m. to 1:30 p.m. on Saturday, April 18, as Patrick Air Force Base hosts a military retiree appreciation day. Retired Lt. Col. Shane Ostrom of the U.S. Air Force will speak at the event. For more information, call 321-494-5463.
APRIL 19
Brushes, paints, canvas, easels, and 25 of the finest Plein Air artists in the nation. The Winter Park Paint Out is back for the seventh year in a row and it’s bigger and more colorful as artists paint scenes in Winter Park and Orlando, capturing moments in time with the splash of oils, watercolors and pastels, from April 19 to 25. The Albin Polasek Museum & Sculpture Gardens, a gem in Central Florida’s Winter Park, will host the seventh annual Winter Park Paint Out. Stop by the museum and gardens to see both artists’ works in progress and recently completed works, watch artists painting in the gardens, and attend free painting demonstrations. Tickets for The Paint Out Garden Party are available through the Polasek Museum. They are priced at $50 in advance, or $80 at the door (if available). Space is limited, and the event has sold out each year. Be sure to purchase your tickets soon and save the date. Call the museum at 407-647-6294 for additional information or visit the Paint Out website at winterparkpaintout.org for a complete schedule of events.
MAY 16
Global funny-man Gabriel Iglesias will be bringing his Laughter Through Unity Tour to the CFE Arena in Orlando on Saturday, May 16, at 7:30 p.m. Iglesias is one of America’s most successful stand-up comedians and he performs in sold-out concerts across the United States and internationally. Tickets are now on sale. Tickets are available through Ticketmaster.com, Ticketmaster outlets, by calling 800-745-3000 or at the CFE Arena Box Office. Sign up for the CFE Arena Cyber Club to receive all the information you need about this event and others, including exclusive presales and discounts, at CFEArena.com