Welcome to the best Winter Garden Events listings online! We aim to be the best source of Winter Garden events, concerts, live music, festivals, parades and other entertainment events by consolidating everything into one list, with events listed in chronological order. If you have a big event you would like to see listed here, let us know! Winter Garden Events, Winter Garden FL 34787 Events.
Here is a list of our yearlong events in Winter Garden for 2022
Recurring Events
Winter Garden plays host to a multitude of events each week. Whether it is lively music you are after, or a trip down memory lane in your favorite antique muscle car we have what you are looking for. Take the vegetables from the farmer’s hands right to your table, or talk shop with a real car buff. Come enjoy yourself at these free events. Winter Garden, FL 34787 events
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Fridays on the Plaza Concert Series 2023When: Every FridayTime: 7:00pm – 9:00pmWhere: Centennial Park Gazebo, 56 W. Plant Street
Farmers Market 2023When: Every SaturdayTime: 8:00am – 1:00pmWhere: City Pavilion, 104 S. Lakeview Ave.Historic Downtown Winter Gardenwww.wintergardenfarmersmarket.com
Open for business
Cruz-n-Car ShowSUSPENDED UNTIL FURTHER NOTICETime: 4:00pm – 8:00pmWhere: Downtown Winter Garden on Plant Street
WINTER GARDEN EVENTS
Special Events
January
Martin Luther King, Jr. CelebrationParade & Live ConcertWhen: Monday, January 16, 2023 Time: 10:00 am – 4:00 pmWhere: Downtown Pavilion, 104 S. Lakeview Avenue Commemorate the life and legacy of Dr. Martin Luther King, Jr. with a community celebration! The event includes a parade, a lineup of live music performances, family friendly activities, displays, and food vendors.This signature City event kicks off at 10:00 am with a Dr. Martin Luther King, Jr. Celebration Parade along Plant Street. To participate in the parade, preregistration is required due to limited space. To submit registration online, click here. To print form and return to Winter Garden Parks & Recreation Department, click here. Parade entry applications must be received no later than Tuesday, January 10, 2023, and will not be accepted after that date. All applicants will receive an email notification stating whether they are approved or not approved. All entries are eligible for the Parade Spirit Award.For those wanting to watch the parade, bring a lawn chair or blanket and head to your favorite viewing spot along Plant Street (from Woodland St. to Central Ave.). Immediately following the parade at about 10:30 am, the celebration continues with a lineup of top-notch music performances at the Downtown Pavilion. The Gerry Williams Band, Craig Thompson Project, and Selwyn Birchwood will be taking the stage throughout the day with the event concluding at 4:00 pm.For more information, please contact Winter Garden Parks and Recreation Department: (407) 656-4155, recinfo@cwgdn.com, 310 North Dillard Street.
February
Winter Garden Heritage & Music FestivalCelebrating the City’s 120th AnniversarySaturday, February 11, 202311:00am-10:00pmHistoric Downtown on Plant Street
Established in 1903, the City of Winter Garden commemorates its heritage with a special 120th anniversary extravaganza. Festivities include six stages of entertainment, strolling performers, and much more! This Winter Garden Heritage & Music Festival is a FREE event for all ages and is brought to you by the City of Winter Garden along with the Winter Garden Heritage Foundation and other generous partners.Live Music & Entertainment, 11:00 am – 10:00 pmSimultaneous and continuous performances will be held at various outdoor stages throughout historic downtown stretching from Central Avenue to Dillard Street. The entertainment kicks off at 11:00 am and continues nonstop through 10:00 pm. For Full List of Activities for this Event Click Here…
March
Shop, Dine & Stroll 2023When: Saturday, March 25All DayWhere: Historic Downtown Winter Garden on Plant StreetOutdoor Shopping & Dining Experience with LIVE MUSIC in picturesque Historic Downtown
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Winter Garden in celebration of the annual National Mom and Pop Business Owners Day!
Live MusicMusic will fill the air as you Shop, Dine & Stroll when a special live music performance by Breezeway Trio takes center stage from 4:00 pm to 7:00 pm. Grab a nearby swing, bench or outdoor table, or bring your own chair for a front row seat. Don’t get too comfortable because the band’s jazz tunes will have you on your feet dancing!-Breezeway Trio Live Music Performance, 4:00 – 7:00 pm-Centennial Plaza Gazebo, Historic DowntownShop, Dine & Stroll will be held rain or shine. Operating hours, sales, and special offers vary per merchant. Participation is at the discretion of the individual retail establishments.For more information…
Evening at the Pops 2023When: Saturday, March 25, 2023Where: Newton Park, Winter GardenBring a blanket or chair and enjoy an outdoor concert under the stars performed by the Space Coast Symphony Orchestra. Newton Park at the shore of Lake Apopka provides a stunning backdrop for this outdoor concert. This is a ticketed event.An Instrument Petting Zoo for children will kick off the event at 4:30 pm.Space Coast Symphony will perform starting at 6:00 pmThe event will be held at Newton Park, 31 W. Garden Avenue, in Winter Garden.Ticket Prices:General Admission: $10 per person (online and at the door)Children 8 and under are FreeVIP: $75 per person (includes reserved seating, dinner, drinks and live entertainment by HAPCO Music Foundation at adjacent Tanner Hall). Available through online purchase only.For more information and to order tickets…
April
May
Winter Garden Memorial Day Community Ceremony 2023When: Monday, May 29Time: 8:15am-9:30amWhere: Veterans Memorial Park420 S. Park Ave.Winter Garden, FL 34787The community is invited to a Roll Call of Veterans, placement of wreaths, and patriotic songs to honor and remember our local veterans who gave their lives during times of war or while serving in the United States armed forces. Please come by to pay homage to those that made the ultimate sacrifice.
June
Winter Garden Farmers Market 15th Birthday CelebrationWhen: Saturday, June 3, 2023Time: 8:00am-1:00pm (Birthday Activities: 9:00am-12:00pm)Where: Downtown Pavilion, 104 Lakeview AvenueWinter Garden, FL 34787The Winter Garden Farmers Market is celebrating its 15th birthday, and you are invited to its party!Visit on Saturday, June 3, for the following FREE birthday-related activities (9:00 am – 12:00 pm):Face PaintingKids Craft Session (Art Table/Tent at Parking Garage Plaza, 160 S. Boyd St.)Giant Lawn Games – Fun for the whole family! (Lawn adjacent to Pavilion)Live MusicTote Bag Giveaway – A commemorative Winter Garden 120th Anniversary Total Bag will be given away to the first 120 guests to the Information Booth at Pavilion entrance (while supplies last).
July
Red, White & Blue Americana Events 2023Downtown Winter Garden turns Red, White, and Blue from Memorial Day through Independence Day, The patriotic decorations pay tribute to America’s holidays while adding nostalgia to the charm of historic downtown.Enjoy the décor while you shop, dine, and stroll. Also, a great backdrop for capturing holiday memories in photos!Download Flyer
19th Annual All American Kids Parade & BreakfastWhen: July 4, 2023Where: Winter Garden Masonic Lodge, 230 W. Bay St.Time: 8:00am-10:30amPancake Breakfast: 8:00-9:45Parade: Line up at 9:45am/Kick Off at 10:00amThe All American Kids Parade is a popular tradition that all ages enjoy! Don you red, white, and blue and parade through historic downtown by foot, bike, scooter, wagon, etc. Wave to family and friends as you stroll by! Or, grab a favorite curbside viewing spot and cheer on the parade as it goes by. Either way, come downtown to be a part of this great 19-year-old tradition that brings the community together to celebrate America’s birthday.BreakfastBefore the Parade, bring the family to a Pancake Breakfast, 8:00 – 9:45 am, at the Masonic Lodge. Kids eat free and breakfast is available for adults to purchase. There is also entertainment and fun activities for the kids!DecorateA variety of complimentary patriotic decorations is available just outside the Lodge to decorate bikes, scooters, wagons, and even your walking shoes, courtesy of the Winter Garden Heritage Foundation.ParadeLine up at the Masonic Lodge at 9:45 am. The Parade kicks off promptly at 10:00 am and loops around downtown’s West Plant Street. The parades lasts about 30 minutes. Everyone is welcome to join the parade of red, white, and blue – on bike, scooter, or foot Spectators are welcome to line the street to get a good viewing spot to cheer on the parade participants. Bring your own chair to watch in comfort.Winter Garden Masonic Lodge No. 165 hosts this event, in collaboration with the City of Winter Garden.
Party in the Park/Fireworks DisplayWhen: July 4, 2023Where: Newton Park on Lake Apopka, 29 W. Garden AvenueTime: 6:00pm-10:00pmFireworks Display: 9:15pmThe City of Winter Garden presents Party in the Park, one of the best firework shows in Central Florida!Party in the Park is a FREE event for the community to celebrate America’s birthday. The SPECTACULAR fireworks display is over Lake Apopka and preshow entertainment includes live music, family activities, and more for all ages. Festivities begin at 6:00 pm. and the Fireworks Show starts at 9:15 pm. Bring a chair or blanket and pack a picnic (no alcohol is permitted) for a fun night under the stars and colorful sky.FESTIVITIESLive Music by Ranahan/Fireworks Show/Games/Crafts/Food & Merchandise Vendors and More!LIVE MUSICRanahan will perform live as part of the preshow activities. The popular band performs country and Caribbean style party music.FIREWORKS DISPLAYThe sky will burst with colors at 9:15 pm as the amazing display of fireworks lights up the night sky with breathtaking reflections on Lake Apopka.PARKINGParking is available at several locations on North Dillard Street.No personal fireworks or alcohol are permitted.
Parking available at Health Central Park and Dillard Street Elementary. Firework display at 9:15pm. In case of a potential rainout please call the rainout hotline number at 407-877-5432.
August
September
October
WINTER GARDEN HALLOWEEN EXPERIENCE:October 20 – October 31, 2022Historic Downtown Winter GardenWhere: Historic Downtown Winter Garden on Plant StreetWhen: October 20 – October 31, 2023Halloween is celebrated for 12 days in Winter Garden! The City’s annual Halloween Experience provides family-friendly festivities in Downtown Winter Garden, including seven nights of an outdoor animated Halloween Light Show on City Hall; a hay maze; fall- and spooky-themed photo locations, decorations and light displays throughout downtown; a Spooky Caboose at the Winter Garden Heritage Museum; a Halloween Celebration at the fall-themed Farmers Market, and more! Costumes are welcome any day!Click here for more information…
November
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Small Business Saturday Sidewalk SaleWhen: Saturday, November 25. 2023Kick off the holiday shopping season at the annual Downtown Winter Garden Small Business Saturday Sidewalk Sale. The mom-and-pop shops in historic downtown make this a must stop to observe the national holiday. Stroll and shop the outdoor sale racks in the festive-decorated historic district. Be sure to pop inside for additional promotions and special savings.
December
Tis the Season Schedule 2022When: December 22-January 8, 2022Downtown Winter Garden transforms into a winter wonderland for 38 days of Tis the Season! Click HERE to learn more about all the free downtown holiday happenings and the seasonal resident programs to make merry memories!
Light Up Winter GardenWhen: Friday, December 2, 2022Time: 6:00-9:00pm (Lighting at 6:15pm)Location: City Hall, 300 W. Plant Street (Lighting) and throughout Historic DowntownJoin us to welcome the holiday season with this annual event to kick off our 38 days of Tis the Season. The lighting will take place at 6:15 pm at City Hall followed by various activities for all to enjoy. Sponsored by Duke Energy and the City of Winter Garden.
Winter Garden Christmas ParadeWhen: Saturday, December 3, 2022Time: 10:00amWhere: South Dillard Street & Plant Street, Historic DowntownBring a lawn chair or blanket and head to your favorite spot for this annual event. A long-standing Winter Garden holiday tradition will delight spectators and bring in holiday cheer! Don’t forget to look for the Big Guy himself at the end of the parade!
Holiday Boutique StrollWhen: Thursday, December 8, 2022Time: 5:00-8:00pmWhere: Historic Downtown Winter GardenHoliday shopping at its finest with a stroll of the boutiques of Downtown Winter Garden to find unique presents while enjoying light refreshments, raffles, outdoor/indoor specials and promotions at participating boutiques. While perusing the outdoor racks and strolling through festive downtown, you will find colorful sights and sounds with enchanting decorations and light displays and holiday music in the air – reminisce of a Hallmark holiday movie!The festively decorated stores and downtown area truly make it a perfect evening for gift buying.
De-light-Ful Decorations Contest 2022Judging: Tuesday, December 13 and Wednesday, December 14 at 5:30pm.Drag out the lights, hang up the garland, put up the glowing Santa and enter your home to win! Festive presentations of outdoor decorations could win up to $100! Winning displays will be posted on the City’s website. For more information about this event, click HERE.
Winter Garden Fire Rescue Annual SANTA RUN 2022“Santa Claus is Coming to Town!”The Winter Garden Fire Rescue annual “SANTA RUN” brings Santa and his sleigh through neighborhoods within city limits! This moving parade takes place on select nights as Santa – along with elves of firefighters, police, and City staff- spread holiday music, treats, and good cheer along the way.Santa will be in the following areas from 5:45 − 9:00 pm on the following dates:• Monday, December 12 − North West Winter Garden • Tuesday, December 13 − North East Winter Garden • Wednesday, December 14 − South Winter Garden: CR 545 Corridor (West Side) • Thursday, December 15 − South Winter Garden: CR 545 Corridor (East Side)• Friday, December 16 − South Winter Garden: CR 535 / Daniel’s Road Corridor• Saturday, December 17 − South Winter Garden: Beulah / Windermere Road Corridor An alternate date is scheduled for December 19 if weather interrupts one of Santa’s visits. For for information click HERE.
Watch video from Santa Run 2014…
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