- December 19, 2025
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MAY 23
Winter Park High School and the Band Booster Board are pleased to announce the spring concert schedule. Concerts are held in the Anne Derflinger Auditorium at Winter Park High School, located at 2100 Summerfield Road. The community is invited to come hear these award-winning young musicians at 7 p.m. on Thursday, May 23. The spring concert features the wind ensemble, symphonic band, concert band and jazz ensemble.
The Orlando Fringe Festival continues this weekend with show times throughout the weekend including “I U We!” a play written by Winter Park mom and musician Molly Conole. The play features a talented local multi-age female cast, appealing to the family friendly demographic while also providing much fun and food for thought for adults. Showtimes are 5:30 p.m. on Thursday, May 23, and 11:15 a.m. on Saturday, May 25. Visit orlandofringe.org for directions to venues.
MAY 24
Central Florida's BBQ Blowout is Central Florida's newest community festival. The Oviedo-Winter Springs Regional Chamber of Commerce and HOPE Helps Inc. are working together to bring residents the event at the Oviedo Mall including a boat show, craft vendors, a mechanical alligator, delicious barbecue and a concert by chart-topping country duo Steel Magnolia. The festival is May 24 and 25 at the Oviedo Mall, located at 1700 Oviedo Mall Blvd. Visit hopehelps.org for more information.
MAY 25
The Parks & Recreation Department of the city of Winter Park is pleased to announce the pool at the Winter Park Community Center, located at 721 W. New England Ave., will re-open for the season on Saturday, May 25. The free celebration from noon to 6 p.m. will feature fun for the entire family including swimming, music and dancing. Visit cityofwinterpark.org for more information.
Superhero Scramble has an upcoming race that will include 8 miles of terrain, more than 25 obstacles, X-treme rock walls, Leap of Faith, water crossings and the super slime slide. Superhero Scramble’s mission is to get people off their couches and into an atmosphere that is out of their comfort zone, which includes wearing a crazy super hero costume! The event goes from 8:45 a.m. to 6 p.m. on Saturday, May 25, at Revolution Off-Road, located at 4000 State Road 33 in Clermont. The event also gives five percent of every registration to charity! Visit superheroscramble.com for more information.
MAY 26
Music at the Casa presents classical guitarist Luis Alfredo Garcia from noon to 3 p.m. on Sunday, May 26, at Casa Feliz, located at 656 N. Park Ave. in Winter Park. Visit casafeliz.org for more information.
MAY 29
Lake Forrest Preparatory School proudly presents “Into the Woods Junior” at 7 p.m. on Wednesday, May 29, at the Trinity Preparatory School Auditorium, located at 5700 Trinity Prep Lane in Winter Park. For more information, please contact Musical Director Margaret Smith at 407-331-5144 or via email at [email protected]