Your free gift from West Orange Bite.
Hi neighbor! Here are the best holiday plans in Winter Garden, Ocoee and nearby this season. Most are free. Save this guide and share it with a friend.
Oranges and Ornaments: A Festival of Trees and Wreaths. See themed holiday trees and wreaths, with seasonal tastings, a raffle and holiday entertainment. The decorated trees are for sale. Friday, Nov. 20, 5:30 to 8:30 PM, Heller Hall, 21 E. Plant St., Winter Garden. Tickets are required and very limited.
Movie in the Park, Ocoee. A city movie night. Friday, Nov. 20, 6 to 9 PM.
Thanksgiving Celebration at the Farmers Market. A free kids' craft from 9 AM to noon at the Parking Garage Plaza, 160 S. Boyd St. The market runs 8 AM to 1 PM at the Downtown Pavilion, 104 S. Lakeview Ave., Winter Garden. A good time to shop for your holiday table. Free.
The Great Turkey Trot 5K. A 5K with kids' races, a finisher medal and an apple cider donut. Sunday, Nov. 22, 8 AM, Southern Hill Farms, 16651 Schofield Rd., Clermont. $40 for the 5K on or after Nov. 7, and $15 for kids' races. It has sold out in past years.
Turkey Day 5K Clermont. Run or walk before the big meal. Thursday, Nov. 26 (Thanksgiving), 9 AM, Waterfront Park, 330 3rd St., Clermont. From Nov. 7 to 25 it costs $45.99 plus a $5.75 sign-up fee.
Small Business Saturday Celebration. Shop small at the downtown sidewalk sale, with live music from 11 AM to 7 PM. Saturday, Nov. 28, all day, historic downtown Winter Garden. Free to attend.
A Holiday Spectacular. A holiday show with Opera Orlando, the Orlando Choral Society and the Winter Garden Community Choir. Saturday, Nov. 28, 7 PM, Garden Theatre, 160 W. Plant St. Get tickets online. VIP seats are $99. All sales are final.
Main Street Holiday Stroll. Walk past holiday trees, lights and photo spots on South Main Street, between W. Plant St. and W. Joiner St., Winter Garden. Dec. 3, 2026, to Jan. 3, 2027, all day. Free.
Light Up Winter Garden. The 39th year. The lights turn on at City Hall at 6:15 PM, with music and holiday fun. Friday, Dec. 4, 6 to 9 PM, City Hall, 300 W. Plant St. Free.
Cookies and Cocoa with Santa, Ocoee. Visit Santa, with cookies, hot cocoa and photos. Friday, Dec. 4, Friday, Dec. 11, and Monday, Dec. 21, at the Withers-Maguire House in Ocoee. Space is limited, so sign up first.
Winter Garden Christmas Parade. Bring a chair and watch for Santa at the end. Saturday, Dec. 5, 10 AM. It starts at Dillard St. and Palmetto St., goes north on Dillard, then west on Plant St. to Park Ave. Free.
Holiday Night Market. Rows of booths with holiday gifts and sweet treats, plus a stage with holiday shows, including local school choruses. Saturday, Dec. 5, 4 to 8 PM, Downtown Pavilion, 104 S. Lakeview Ave. Free to attend.
Christmas Golf Cart Parade. Golf carts covered in lights roll through downtown. Saturday, Dec. 5, 6 PM, West Plant St. Free to watch.
A Merry Winter Garden Light Show. City Hall turns into a 25-minute light show set to music. It plays on a loop from 6 to 9 PM on Dec. 4, 5, 6, 11, 12, 13, 18, 19, 20, 26 and 27, at 300 W. Plant St. Street performers stroll downtown on the same nights. Free.
Chanukah Celebration and Menorah Lighting. Hosted by Chabad of Winter Garden. Tuesday, Dec. 8, 6 to 8:30 PM, Downtown Pavilion and Butterfly Sculpture Park, 104 S. Lakeview Ave.
It's a Wonderful Life: A Live Radio Play. The classic story, told like a 1940s radio show. Dec. 9 to 20, with afternoon and evening shows on select dates, at the Garden Theatre, 160 W. Plant St. Tickets required.
Live Holiday Music on the Plaza. Free holiday music at the Centennial Plaza gazebo, 7 to 9 PM. Dickens Carolers on Dec. 11, Santa Sisters on Dec. 12, Mistletones on Dec. 18 and Atlantic City Boys on Dec. 19.
Santa at the Farmers Market. Santa visits to hear wish lists and pose for free photos. Saturdays, Dec. 12 and Dec. 19, 9 AM to noon. The market is open 8 AM to 1 PM every Saturday in December at 104 S. Lakeview Ave.
Jolly Jamboree and Tree Lighting, Ocoee. A kids' zone, special guests and a tree lighting. Saturday, Dec. 12. Free.
$5 Holiday Flix at the Garden. Holiday movies at the Garden Theatre, 160 W. Plant St. "It's a Wonderful Life," Tuesday, Dec. 15, 7 PM. "Elf," Tuesday, Dec. 22, 10 AM and 7 PM. "Christmas with the Kranks," Tuesday, Dec. 29, 7 PM. $5 plus a 79-cent fee, online only, final sale. Free parking in the garage at 160 S. Boyd St.
Holiday Gifts for Kids Toy Drive. The Winter Garden Police Athletic League collects new, unwrapped toys for Winter Garden kids in need, from newborns to age 12. No wrapped toys, toy guns or toy weapons. Nov. 1 to Dec. 11 at the Winter Garden Police Department, 251 W. Plant St.
Christmas Carnival. Matthew's Hope hosts a Christmas carnival for kids, with toy gifts for the families it serves. Tap the name to see how you can help. Saturday, Dec. 12, 10 AM to 2 PM, 611 Business Park Blvd., Winter Garden.
Free guides: Cheap Eats, Hidden Gems.
Towns: Winter Garden, Windermere, Ocoee, Horizon West.
Know a holiday event we missed? Email [email protected].
Free every Friday: places to eat and fun things to do this weekend in West Orange.