Winter WondORLAND Grew From One Night Into Three December Saturdays on the Village Green

Last year, Winter WondORLAND was a theme. The Village of Orland Park used the name for its annual Christmas Parade, Tree Lighting and Festival, held over one Sunday evening, Nov. 30, 2025, from 4 to 7 p.m. at the Village Center on Ravinia Avenue. This year the name covers a separate series. Winter WondORLAND now has three Saturday evenings of its own on the Village Green in December, each with an iceless skating rink, food trucks, a DJ and a different set of characters.

So Orland Park's holiday season now runs four Saturdays in a row at 14700 S. Ravinia instead of happening on one night. Meanwhile, the village's planned permanent winter rink belongs to a downtown park with a 2027 completion target.

The parade moves to Saturday and starts an hour later

The season opens with the Christmas Parade, Tree Lighting & Festival, presented by Mazda of Orland Park, on Saturday, Nov. 28, from 5 to 8 p.m. at the Village Green, according to the village's event listing. In 2025 it was a Sunday that started at 4 p.m., so this year's shift puts it on a Saturday night and an hour later.

Here is how the evening runs, according to the village:

1. 5 p.m.: The Holiday Lights on Ravinia parade heads north on Ravinia from 151st Street to 147th Street. More than 40 participants are expected, including Scouts, church and youth groups, dance groups, bands and local businesses. Every entry has to be at least 50% light elements.
2. About 6 p.m.: Once the parade ends, the Carl Sandburg High School Chamber Singers lead carols just east of Village Hall. Then Mayor Jim Dodge leads the countdown to the tree lighting.
3. After the lighting: A holiday drone show plays over the John Humphrey Complex.
4. Inside Village Hall: Photos with Santa next to a 20-foot tree and train set. Every child gets a free plush starting at 6 p.m.
5. Inside the Civic Center: Local dance groups perform and holiday market vendors set up in the Annex Room. The Exhibition Room has winter crafts, a Snow Globe photo spot and the Gingerbread Toddler Playland.

Outside, there are fire pits and food vendors around the lighted displays on the village lawn, plus meet-and-greets with Clarice and Rudolph. The Creamery sells hot chocolate from two stations inside the Civic Center and from its food truck outside.

The drone show builds on last year's finale. A Citizen Portal recap of the 2025 parade described that night's ending as the village's first combined fireworks-and-drone show. This year's listing calls the post-lighting show a holiday-themed drone show.

If you live near Ravinia, plan around the closures. The village lists Ravinia between 151st and 149th as closed from 3:30 to 5:30 p.m. and between 144th and 149th from 4:30 to 6:30 p.m. Both windows can change, and police decide when it's safe to reopen.

Last year's festival extras now get their own Saturdays

The 2025 festival packed a lot into three hours. It had live reindeer, Anna and Elsa at a Princess Palace, a Candyland bounce house, photos in Santa's sleigh and a snowball fight with Olaf in the Exhibition Room.

In 2026, those headline characters are spread across December. Each Winter WondORLAND night runs 5 to 8 p.m. outside on the Village Green, it's free and open to all ages, and each Saturday has its own lineup:

The village lists the details on its Dec. 5, Dec. 12 and Dec. 19 event pages. Three practical points from those pages: only a limited number of skates are available each night, skating time may be limited, and activities can change with the weather. If your kids are coming for the rink, get there close to 5 p.m.

The decorated trees on the lawn tie the nights together. In its 2025 festival announcement, the village explained that the Orland Park Lions Club donates the community trees, and local groups, families, businesses and organizations "adopt" and decorate them. The tree lighting turns on those displays across the Village Green. All three Winter WondORLAND listings name the lighted displays and decorated trees as part of the evening, so the Nov. 28 lighting effectively sets up the next three Saturdays.

Dec. 5 is the busiest day of the stretch. Earlier that morning, the village calendar lists Santa's Pit Stop from 9 a.m. to noon.

The permanent rink is planned for Heroes Park, with a 2027 target

The village's long-term plan for winter skating is in the Main Street Triangle, near 143rd Street, LaGrange Road and the 143rd Street Metra station. That's where Crescent Park is set to be expanded into Heroes Park.

Southwest Regional Publishing reported in June that the expanded park is designed as a central hub for farmers' markets, summer concerts, a pedestrian boardwalk and a winter ice skating rink. In its June 16, 2026 announcement, the village gave a construction start target of late summer 2026 and a completion target of summer 2027.

The same announcement explains part of how the park will be paid for. Under a new ground lease, University of Chicago Medicine will build a musculoskeletal center of roughly 80,000 to 120,000 square feet at the northwest corner of 143rd Street and LaGrange Road. The village is earmarking $10.16 million in ground rent over 25 years, plus $322,500 a year from UCMC's lease of 215 garage stalls, to help cover Heroes Park construction, debt service and operations. The roughly 547-stall garage stays open to the public on evenings, weekends and holidays.

The latest board action on record is about what's underground. On Oct. 5, 2026, the Village Board finalized added construction-observation services for downtown utility relocation, after two detention vaults were added to the Heroes Park design. Southwest Regional Publishing put the rest of the downtown commercial buildout on a rolling fall 2027 schedule.

We covered the background on the Triangle in our look at what's actually open at Downtown Orland Park right now.

What's around the edges of the Village Green nights

Some of the season happens away from Ravinia.

Orland Square. The mall's Santa season started early. Its Santa Arrival Party and tree lighting were Nov. 6 at the Cheesecake Factory entrance, and Santa photos continue through Dec. 24. Two sessions are worth putting on the calendar now. Caring Santa is Sunday, Dec. 6, from 9:30 to 10:30 a.m., and Santa Paws is Sunday, Dec. 13, from 5:30 to 7 p.m., according to Orland Square's holiday page. Both fall the morning or evening after a Winter WondORLAND Saturday.

Crescent Park Circle. Mala Sweets is a dessert-and-drink café at Ninety7Fifty on the Park, 9750 Crescent Park Circle. Patch reported that its menu includes croffles, cakes, gelato, coffee, matcha, hojicha, smoothies and refreshers.

Wolf Road. Joey's Red Hots moved across Wolf Road into a 7,000-square-foot space at 17259 Wolf Rd., which opened Oct. 2, according to Patch. If you remember the old spot, the new one is across the road.

The four Saturdays at a glance

• Nov. 28: Parade at 5 p.m., tree lighting around 6 p.m., then the drone show
• Dec. 5: Santa's Pit Stop from 9 a.m. to noon, then Winter WondORLAND from 5 to 8 p.m. with carolers
• Dec. 12: Winter WondORLAND with live reindeer, the Grinch and Cindy Lou Who
• Dec. 19: Winter WondORLAND with ice carving, Anna, Elsa and Olaf

The village's Recreation and Parks Department takes questions about the holiday events at 708-403-5000.

Living near the Village Green or the future Heroes Park changes what an Orland Park home offers in December. If you're wondering how projects like these affect what your place is worth, Jeff / Amjad Salhani & Associates can walk you through it over coffee. Let's connect, and get your free home valuation.