LET’S MARK OUR CALENDARS

At Dinner on the Avenue, friends, families, co-workers and neighbors organize groups and decorate tables based upon themes of their choosing. The next installment of the annual event is slated for April 2, 2022.

The events listed below are ones scheduled as of press time. However, because of continued uncertainty surrounding the COVID-19 pandemic, we highly recommend checking the appropriate websites for the most up-todate information as there’s always the possibility that events may be canceled or altered due to public health considerations.

WINTER PARK AUTUMN ART FESTIVAL

OCTOBER 9–10, 2021 Central Park, Park Avenue The Winter Park Chamber of Commerce brings this community-oriented outdoor festival to the City of Culture and Heritage in the fall. The two-day juried fine art show, which draws more than 40,000 people, features work exclusively by Florida-based artists as well as live entertainment and food. Children’s art workshops are also offered. 9 a.m.–5 p.m. both days. The dates have already been set for 2022: October 15 and 16. Free. 407-644-8281. autumnartfestival.org

WINTER PARK PAINT OUT

OCTOBER 10–16, 2021 Albin Polasek Museum & Sculpture Gardens Although the Paint Out was canceled in April 2020 due to the pandemic, it’ll be back in October 2021 for its lucky 13th incarnation. The Polasek Museum & Sculpture Gardens, formerly the home and studio of the late sculptor Albin Polasek, will host 24 professionally acclaimed plein air artists, who roam the city to capture favorite landscapes and landmarks with oils, watercolors and pastels. The complex, at 633 Osceola Avenue, is open to the public free of charge during the event. As always, newly finished paintings will be hung in the gallery’s “wet room” and will be available for purchase. Artwork will also be viewable online as it is created at winterparkpaintout.org. 407-6476294. polasek.org

HOLIDAY POPS CONCERT

DECEMBER 2021 (DATE TBA) Central Park, Park Avenue Bring a blanket and a picnic basket and get ready for an Orlando Philharmonic Orchestra program of holiday favorites that will be certain to put everyone in a happy and hopeful seasonal frame of mind. Free. cityofwinterpark.org/events

43RD ANNUAL CHRISTMAS IN THE PARK

DECEMBER 2, 2021 Central Park, Park Avenue Since 1979, the Charles Hosmer Morse Museum of American Art has helped launch the holiday season in Winter Park with a breathtaking display of Louis Comfort Tiffany’s leaded-glass windows in Central Park. The outdoor exhibition of back-lit masterpieces is accompanied by performances from the Bach Festival Choir, Youth Choir and Brass Ensemble. The tradition was started by Hugh and Jeannette McKean, the museum’s founders and benefactors, to display their beloved Tiffany treasures in an informal and accessible setting. The event, which usually runs from 6:15–8 p.m. on the Central Park stage, is free. morsemuseum.org

WINTER ON THE AVENUE, FEATURING HOLIDAY TREE LIGHTING

DECEMBER 3, 2021 Central Park, Park Avenue The Winter Park Chamber of Commerce and the City of Winter Park host a holiday season kickoff, presented this year by

Westminster Winter Park. The street party includes a flurry of activities from 5-9 p.m. along Park Avenue and in Central Park. The annual tree-lighting ceremony at dusk includes performances by children’s choirs as well as activities for youngsters. The date has already been set for 2022: December 2. cityofwinterpark.org

YE OLDE HOMETOWN CHRISTMAS PARADE

DECEMBER 4, 2021 Park Avenue, from Canton to New England to Pennsylvania avenues The city’s annual Christmas Parade has been held on the first Saturday in December for more than six decades, making it the longest-running parade in Central Florida. More than 100 units march south down Park Avenue between 9-10:30 a.m.; highlights include local dance troupes, police and fire departments, marching bands, Scout troops, local dignitaries and, of course, Santa Claus (the real one). Before and during the parade, Leadership Winter Park hosts its annual Pancake Breakfast at the Central Park stage from 7-10:30 a.m. Proceeds from the breakfast benefit the Winter Park Improvement Foundation. The date has already been set for 2022: December 2. winterpark.org

SIP, SHOP AND STROLL

DECEMBER 9, 2021 Park Avenue Spend the evening strolling through downtown Winter Park, visiting shops and restaurants. Brought to you by the Winter Park Chamber of Commerce and the Park Avenue Merchants Association, the annual event gives visitors the opportunity to check out merchant offerings and sample seasonal menu items, enjoying wine and hors d’oeuvres along the way, 5–8 p.m. winterpark.org

WINTER PARK SIDEWALK ART FESTIVAL

MARCH 18–20, 2022 Central Park, Park Avenue This annual, nationally ranked juried arts fest features some 200 artists chosen by a panel of judges from more than 1,100 applicants. The three-day outdoor event also features live music and children’s activities. (Pets are not allowed in the park or along the avenue between New England and Canton avenues during the festival.) Free. Friday and Saturday, 9 a.m.–6 p.m.; Sunday, 9 a.m.–5 p.m. wpsaf.org

ADVENTHEALTH WINTER PARK ROAD RACE

MARCH 12, 2022 Central Park, 251 North Park Avenue The AdventHealth Winter Park Road Race is a local tradition and the grand finale each year of the region’s Track Shack Running Series. In addition to the 10K main event, it offers a 2-mile race and a kids’ run so the whole family can participate. The 6.2-mile route features slight inclines, tree-lined streets, historic homes and views of the Winter Park Chain of Lakes as it passes through several of the city’s beautiful neighborhoods. Race details, including start times, were still being decided at press time. Check back at trackshack.com.

TASTE OF WINTER PARK

MARCH 23, 2022 Winter Park Farmers’ Market, 200 West New England Avenue This foodie festival, organized by the Winter Park Chamber of Commerce, showcases more than 40 of the region’s top chefs, bakers, caterers and confectioners. Admission to the event, which runs from 5–8 p.m., includes unlimited samples of signature dishes, beverages and desserts as well as live entertainment and raffle prizes. 407644-8281. winterpark.org.

EARTH DAY IN THE PARK

APRIL 2022 (DATE TBA) Central Park, Park Avenue This city-sponsored event, presented by its Sustainability Program and Keep Winter Park Beautiful Program, includes interactive, educational and entertaining activities for all ages, including live music, yoga classes, an electric vehicle display and booths manned by environmental advocacy groups. Residents and visitors are encouraged to carpool or bike/walk to the event. 407-599-3364. cityofwinterpark.org/earthday

DINNER ON THE AVENUE

APRIL 2, 2022 Park Avenue between New England Avenue and Morse Boulevard Each year the city shuts down a stretch of Park Avenue for the evening so that cars can be replaced by tables and white linen for a unique, fun-filled dining experience and social event from 6–10 p.m. Friends, families, co-workers and neighbors organize groups, decorate tables based upon themes of their choosing, then sit down to potluck or catered dinners. cityofwinterpark.org/events

EASTER EGG HUNT

APRIL 16, 2022 Central Park, Park Avenue This city-organized event is BYOB (Bring Your Own Basket). Children up to age 10 may hunt for the more than 10,000 eggs placed throughout Central Park. Anyone who comes up empty-handed can still enjoy special treats distributed at a designated candy area. Children with special needs are encouraged to join in the fun. 9:30–11 a.m., with the hunt starting promptly at 10 a.m. Free. cityofwinterpark.org/events

WINTER PARK PAINT OUT

APRIL 24–30, 2022 Albin Polasek Museum & Sculpture Gardens The Albin Polasek Museum & Sculpture Gardens, formerly the home and studio of the late sculptor Albin Polasek, hosts professionally acclaimed plein air artists, who roam the city to capture favorite landscapes and landmarks with oils, watercolors and pastels. The complex, at 633 Osceola Avenue, is open to the public free of charge during the event. As always, newly finished paintings are hung in the gallery’s “wet room” and may be purchased on the spot. 407-6476294. polasek.org.

OLDE FASHIONED 4TH OF JULY CELEBRATION

JULY 4, 2022 Central Park, Park Avenue and Morse Boulevard Central Park is the site of this annual Independence Day celebration, with patriotic music performed by the Bach Festival Brass Band and Bach Festival Choir. There’s also a sunrise 5K run as well as other musical performances and an annual bicycle parade for children. Watermelon and water are served. Also, during the celebration admission is free to the Charles Hosmer Morse Museum of American Art and the Winter Park History Museum (hours may vary). cityofwinterpark.org/events