Orlando Adult Golf Night Pt.2 Fri 28 Aug 2026, 6:30 PM — Live music Stoneybrook West Golf Club · 15501 Towne Commons Boulevard, Winter Garden, FL 34787
CITY LIGHTS: LIGHT SHIFT | Live Music + Open Mic Experience Fri 28 Aug 2026, 7:45 PM — Live music West Orange Dream Center · 1136 East Plant Street, Winter Garden, FL 34787
Garden Sessions - Live for a Cure Sat 29 Aug 2026, 5:00 PM — Live music Home State Brewing Co. · 16016 New Independence Parkway #100, Winter Garden, FL 34787
Pulse Elite Glow in the Dark Ride Sat 29 Aug 2026, 6:00 PM — class 1015 S Dillard St · 1015 South Dillard Street, Winter Garden, FL 34787
Winter Garden Date Night Mystery Tue 1 Sep 2026, 10:00 AM — Meetup 101 W Plant St · 101 West Plant Street, Winter Garden, FL 34787
Winter Garden Love on the Rails Quest Tue 1 Sep 2026, 10:00 AM — Meetup 101 W Plant St · 101 West Plant Street, Winter Garden, FL 34787
College Night @ Senor Frogs Orlando Tuesdays - Party Bus Tue 1 Sep 2026, 11:00 PM — Meetup 2272 Western Way · 2272 Western Way, Winter Garden, FL 34787 · 18+
Fused Glass Pendant Jewelry Thu 3 Sep 2026, 10:00 AM — class The Grotto at Stoneybrook West · 12572 Stoneybrook West Parkway, Winter Garden, FL 34787
Cool Cancer Group Sun 6 Sep 2026, 2:00 PM — Meetup Healthy West Orange · 1200 East Plant Street #Suite 200, Winter Garden, FL 34787
Weekends in Winter Garden: Foodies + New Friends Sun 6 Sep 2026, 7:00 PM — Meetup Restaurant of the Weekend · West Plant Street, Winter Garden, FL 34787
Paint Your Own Pet Sat 12 Sep 2026, 10:00 AM — class The Grotto at Stoneybrook West · 12572 Stoneybrook West Parkway, Winter Garden, FL 34787
UNO Winter Garden - Deep Dish Pizza Cooking Class and Lunch Sat 12 Sep 2026, 12:00 PM — class UNO Pizzeria & Grill · 3167 Daniels Road, Winter Garden, FL 34787
Zen at Ten Sun 13 Sep 2026, 10:00 AM — class Home State Brewing Co. · 16016 New Independence Parkway #100, Winter Garden, FL 34787
Bonsai & Cheers at Home State Brewing | Powder Puff Bonsai Workshop Sun 13 Sep 2026, 11:30 AM — class Home State Brewing Co. · 16016 New Independence Parkway #100, Winter Garden, FL 34787
September Mahjong Open Play at LiveTrends Boutique Tue 15 Sep 2026, 6:00 PM — Theater LiveTrends Boutique · 279 Tremaine Street, Winter Garden, FL 34787
September Mahjong 101 - Winter Garden Wed 16 Sep 2026, 6:00 PM — class Tanner Hall · 29 West Garden Avenue, Winter Garden, FL 34787
Yoga & Beer Sun 20 Sep 2026, 10:00 AM — class Crooked Can Brewing Company · 426 West Plant Street, Winter Garden, FL 34787
Let's Dance! Zumba with Studio K Wed 23 Sep 2026, 6:00 PM — class Healthy West Orange Building · 1200 East Plant Street, Winter Garden, FL 34787
Winter Garden Date Night Mystery Thu 1 Oct 2026, 10:00 AM — Meetup 101 W Plant St · 101 West Plant Street, Winter Garden, FL 34787
Now Serving Beer & Wine | Harrell's Hot Dogs + Cold Cones Thu 1 Oct 2026, 11:00 AM — Meetup Harrell's Hot Dogs + Cold Cones · 54 West Plant Street, Winter Garden, FL 34787
New Dirty Sodas | Harrell's Hot Dogs + Cold Cones Thu 1 Oct 2026, 11:00 AM — Meetup Harrell's Hot Dogs + Cold Cones · 54 West Plant Street, Winter Garden, FL 34787
Up To No Good Thursdays | Harlow Grove Thu 1 Oct 2026, 8:00 PM — Live music Harlow Grove · 186 South Main Street, Winter Garden, FL 34787
Weekends At The Grove| Harlow Grove Fri 2 Oct 2026, 9:00 PM — Live music Harlow Grove · 186 South Main Street, Winter Garden, FL 34787
Brunch At Harlow Grove Sat 3 Oct 2026, 10:00 AM — Meetup Harlow Grove · 186 South Main Street, Winter Garden, FL 34787
UNO Winter Garden - Deep Dish Pizza Cooking Class and Lunch Sat 3 Oct 2026, 12:00 PM — class UNO Pizzeria & Grill · 3167 Daniels Road, Winter Garden, FL 34787
Johns Lake Ward Sacrament Meeting Sun 4 Oct 2026, 12:00 PM — Meetup The Church of Jesus Christ of Latter-day Saints · 3850 Avalon Rd, Winter Garden, FL 34787
Cool Cancer Group Sun 4 Oct 2026, 2:00 PM — Meetup Healthy West Orange · 1200 East Plant Street #Suite 200, Winter Garden, FL 34787
Weekends in Winter Garden: Foodies + New Friends Sun 4 Oct 2026, 7:00 PM — Meetup Restaurant of the Weekend · West Plant Street, Winter Garden, FL 34787
What's On Your November Ballot? Tue 6 Oct 2026, 6:00 PM — Meetup First United Methodist Church of Winter Garden · 125 North Lakeview Avenue, Winter Garden, FL 34787
College Night @ Senor Frogs Orlando Tuesdays - Party Bus Tue 6 Oct 2026, 11:00 PM — Meetup 2272 Western Way · 2272 Western Way, Winter Garden, FL 34787 · 18+
Yoga & Beer Sun 18 Oct 2026, 10:00 AM — class Crooked Can Brewing Company · 426 West Plant Street, Winter Garden, FL 34787
Bonsai & Cheers at Home State Brewing | Hawaiian Umbrella Bonsai Workshop Sun 25 Oct 2026, 11:30 AM — class Home State Brewing Co. · 16016 New Independence Parkway #100, Winter Garden, FL 34787
New Independence Ward Sacrament Meeting Sun 25 Oct 2026, 1:30 PM — Meetup The Church of Jesus Christ of Latter-day Saints · 3850 Avalon Rd, Winter Garden, FL 34787
Winter Garden Date Night Mystery Sun 1 Nov 2026, 10:00 AM — Meetup 101 W Plant St · 101 West Plant Street, Winter Garden, FL 34787
Brunch At Harlow Grove Sun 1 Nov 2026, 10:00 AM — Meetup Harlow Grove · 186 South Main Street, Winter Garden, FL 34787
Now Serving Beer & Wine | Harrell's Hot Dogs + Cold Cones Sun 1 Nov 2026, 11:00 AM — Meetup Harrell's Hot Dogs + Cold Cones · 54 West Plant Street, Winter Garden, FL 34787
New Dirty Sodas | Harrell's Hot Dogs + Cold Cones Sun 1 Nov 2026, 11:00 AM — Meetup Harrell's Hot Dogs + Cold Cones · 54 West Plant Street, Winter Garden, FL 34787
New Independence Ward Sacrament Meeting Sun 1 Nov 2026, 1:30 PM — Meetup The Church of Jesus Christ of Latter-day Saints · 3850 Avalon Rd, Winter Garden, FL 34787
Cool Cancer Group Sun 1 Nov 2026, 2:00 PM — Meetup Healthy West Orange · 1200 East Plant Street #Suite 200, Winter Garden, FL 34787
Weekends in Winter Garden: Foodies + New Friends Sun 1 Nov 2026, 7:00 PM — Meetup Restaurant of the Weekend · West Plant Street, Winter Garden, FL 34787
College Night @ Senor Frogs Orlando Tuesdays - Party Bus Tue 3 Nov 2026, 11:00 PM — Meetup 2272 Western Way · 2272 Western Way, Winter Garden, FL 34787 · 18+
Up To No Good Thursdays | Harlow Grove Thu 5 Nov 2026, 8:00 PM — Live music Harlow Grove · 186 South Main Street, Winter Garden, FL 34787
Weekends At The Grove| Harlow Grove Fri 6 Nov 2026, 9:00 PM — Live music Harlow Grove · 186 South Main Street, Winter Garden, FL 34787
Sell your camera gear (free event-no ticket needed) at The Lens Pal Fri 13 Nov 2026, 9:00 AM — Meetup The LensPal · 213 South Dillard Street #STE 330, Winter Garden, FL 34787
UNO Winter Garden - Deep Dish Pizza Cooking Class and Lunch Sat 14 Nov 2026, 12:00 PM — class UNO Pizzeria & Grill · 3167 Daniels Road, Winter Garden, FL 34787
Oranges and Ornaments: A Festival of Trees and Wreaths Fri 20 Nov 2026, 5:30 PM — Live music The Winter Garden Heritage Foundation - Healthy West Orange Heritage and Cultural Center · 21 East Plant Street, Winter Garden, FL 34787
Brunch Among the Trees: An Oranges & Ornaments Culinary Experience Sat 21 Nov 2026, 11:00 AM — Live music The Winter Garden Heritage Foundation - Healthy West Orange Heritage and Cultural Center · 21 East Plant Street, Winter Garden, FL 34787
Johns Lake Ward Sacrament Meeting Sun 6 Dec 2026, 12:00 PM — Meetup The Church of Jesus Christ of Latter-day Saints · 3850 Avalon Rd, Winter Garden, FL 34787
BOOSTER BOS$ 2027 Sat 13 Feb 2027, 8:00 AM — Meetup 17800 Bali Blvd · 17800 Bali Boulevard, Winter Garden, FL 34787
Listings are seeded from venue and organiser calendars. See them on the map.