53 upcoming listings — live music, theater, markets, drag, comedy and more, each with a time, a venue and a street address.
What's coming up
Winter Haven Toastmasters Tue 25 Aug 2026, 6:30 PM — Meetup 656 Ave L NW · 656 Avenue L Northwest, Winter Haven, FL 33881
Smile City Comedy Show! with Rob Smiles Thu 27 Aug 2026, 8:00 PM — Comedy 19 3rd St NW · 19 3rd Street Northwest, Winter Haven, FL 33881
Stuffed Animal Flight School - Winter Haven Campus Fri 28 Aug 2026, 4:00 PM — Meetup Winter Haven Public Library · 325 Avenue A Northwest, Winter Haven, FL 33881
Jake Klark from Comic Strip LIVE! Fri 28 Aug 2026, 8:00 PM — Comedy 19 3rd St NW · 19 3rd Street Northwest, Winter Haven, FL 33881
She Reps: Reps & Recovery Sat 29 Aug 2026, 10:00 AM — class 1100 Fairfax St NE · 1100 Fairfax Street Northeast, Winter Haven, FL 33881
Bedazzling Class Sat 29 Aug 2026, 2:00 PM — class Manely Beauty · 301 3rd street nw unit 357, Winter haven, FL 33881
Pizza & Wine Night - Winter Haven Sat 29 Aug 2026, 6:30 PM — Meetup The Treasured Olive · 52 4th Street Northwest, Winter Haven, FL 33881
Women’s Wellness Workshop Sun 30 Aug 2026, 3:00 PM — class FLAME candlestudios · 25 3rd Street Northwest, Winter Haven, FL 33880
Art for Mental Health Guided Drawing Thu 3 Sep 2026, 11:00 AM — class Winter Haven Recreation and Cultural Center · 801 MLK Blvd, Winter Haven, FL 33881
The Boarding Pass: Business Networking Ready For Takeoff Thu 3 Sep 2026, 2:00 PM — Meetup Flightline Cafe & Catering · 2073 U.S. 92 #West, Winter Haven, FL 33881
The Dish Rack Comedy Show! Thu 3 Sep 2026, 8:00 PM — Comedy 19 3rd St NW · 19 3rd Street Northwest, Winter Haven, FL 33881
KARAOKE AT KULTURE ON 1ST Thu 3 Sep 2026, 8:00 PM — Karaoke KULTURE ON 1ST · 1780 1st Street North, Winter Haven, FL 33881
Matt Fernandez from Funny or Die! Fri 4 Sep 2026, 8:00 PM — Comedy 19 3rd St NW · 19 3rd Street Northwest, Winter Haven, FL 33881 · 21+
SUNDAZE AT KULTURE ON 1ST Sun 6 Sep 2026, 8:00 PM — Meetup KULTURE ON 1ST · 1780 1st Street North, Winter Haven, FL 33881
FLORIDA PRO WRESTLING - at Tanners Lakeside Fri 11 Sep 2026, 8:00 PM — Sports Tanners Lakeside Restaurant & Bar · 1006 Lake Howard Drive Southwest, Winter Haven, FL 33880
Johnny B from 102.5 The Bone! Fri 11 Sep 2026, 8:00 PM — Comedy 19 3rd St NW · 19 3rd Street Northwest, Winter Haven, FL 33881
CERTIFIED Basic Handgun Training Sat 12 Sep 2026, 9:00 AM — class 3812 Cypress Gardens Rd · 3812 Cypress Gardens Road, Winter Haven, FL 33884
Growing and Caring for Succulents Mon 14 Sep 2026, 10:00 AM — class Winter Haven Public Library · 325 Avenue A Northwest, Winter Haven, FL 33881
The Bucket List! Thu 17 Sep 2026, 8:00 PM — Comedy 19 3rd St NW · 19 3rd Street Northwest, Winter Haven, FL 33881
Jerry Wayne Longmire from The Reckon Yard Podcast! Fri 18 Sep 2026, 8:00 PM — Comedy 19 3rd St NW · 19 3rd Street Northwest, Winter Haven, FL 33881
Selling Smart in 2026: What Every Polk County Homeowner Needs to Know Sat 19 Sep 2026, 10:00 AM — class 245 W Central Ave suite 101 · 245 West Central Avenue #suite 101, Winter Haven, FL 33880
The Beauty Mixer & Workshop "A Brunch for Alignment" presented by ZK Beauty Sat 19 Sep 2026, 11:00 AM — class RainDance · 200 Avenue C Southwest, Winter Haven, FL 33880
The Central Florida Food Truck Rally (Blu Summers Inc.) Sat 19 Sep 2026, 4:00 PM — Live music Boys & Girls Clubs of Polk County, George Jenkins Memorial Unit · 2400 Havendale Boulevard Northwest, Winter Haven, FL 33881
The Central Florida Food Truck Rally (Friends and Family of My Touch) Sat 19 Sep 2026, 4:00 PM — Live music Boys & Girls Clubs of Polk County, George Jenkins Memorial Unit · 2400 Havendale Boulevard Northwest, Winter Haven, FL 33881
The Central Florida Food Truck Rally (Official MCee Smart Mouth) Sat 19 Sep 2026, 4:00 PM — Live music Boys & Girls Clubs of Polk County, George Jenkins Memorial Unit · 2400 Havendale Boulevard Northwest, Winter Haven, FL 33881
The Central Florida Food Truck Rally (Boys & Girls Club of Polk County Sat 19 Sep 2026, 4:00 PM — Live music Boys & Girls Clubs of Polk County, George Jenkins Memorial Unit · 2400 Havendale Boulevard Northwest, Winter Haven, FL 33881
Work Sucks: A Comedy Showcase! Thu 24 Sep 2026, 8:00 PM — Comedy 19 3rd St NW · 19 3rd Street Northwest, Winter Haven, FL 33881
Stephen Henry: Best of the Bay! Fri 25 Sep 2026, 8:00 PM — Comedy 19 3rd St NW · 19 3rd Street Northwest, Winter Haven, FL 33881
Basic Handgun Training: This class teaches the basics of handgun use Sat 26 Sep 2026, 9:00 AM — class 3812 Cypress Gardens Rd · 3812 Cypress Gardens Road, Winter Haven, FL 33884
Petals & Prestige Hands-On Floral Workshop Sat 26 Sep 2026, 12:00 PM — class 2110 Oakhurst Dr · 2110 Oakhurst Drive, Winter Haven, FL 33881
KARAOKE AT KULTURE ON 1ST Thu 1 Oct 2026, 8:00 PM — Karaoke KULTURE ON 1ST · 1780 1st Street North, Winter Haven, FL 33881
Keith Lenart from Last Comic Standing! Fri 2 Oct 2026, 8:00 PM — Comedy 19 3rd St NW · 19 3rd Street Northwest, Winter Haven, FL 33881
SUNDAZE AT KULTURE ON 1ST Sun 4 Oct 2026, 8:00 PM — Meetup KULTURE ON 1ST · 1780 1st Street North, Winter Haven, FL 33881
Stormy Daniels: Unicorns in the Kitchen Tour! Fri 9 Oct 2026, 8:00 PM — Comedy 19 3rd St NW · 19 3rd Street Northwest, Winter Haven, FL 33881
Ric Diez from Kill Tony! Sun 11 Oct 2026, 8:00 PM — Comedy 19 3rd St NW · 19 3rd Street Northwest, Winter Haven, FL 33881
Winter Haven Toastmasters Tue 13 Oct 2026, 6:30 PM — Meetup 656 Ave L NW · 656 Avenue L Northwest, Winter Haven, FL 33881
DC Benny from Showtime at the Apollo! Fri 16 Oct 2026, 8:00 PM — Comedy 19 3rd St NW · 19 3rd Street Northwest, Winter Haven, FL 33881
Selling Smart in 2026: What Every Polk County Homeowner Needs to Know Sat 17 Oct 2026, 10:00 AM — class 245 W Central Ave suite 101 · 245 West Central Avenue #suite 101, Winter Haven, FL 33880
Winter Haven High School Athletic Hall of Fame Sat 17 Oct 2026, 6:00 PM — Meetup Heartland Church · 225 Avenue B Northwest, Winter Haven, FL 33881
The Gospel of the Kingdom Fri 23 Oct 2026, 6:00 PM — class Southside Baptist Church · 1301 7th Street Southwest, Winter Haven, FL 33880
Lou Angelwolf from Open Bar Comedy! Fri 23 Oct 2026, 8:00 PM — Comedy 19 3rd St NW · 19 3rd Street Northwest, Winter Haven, FL 33881
Women Veterans Expo Sat 24 Oct 2026, 10:00 AM — Meetup American Legion Post 8 · 300 Avenue M Northwest, Winter Haven, FL 33881
Chili cookoff and Trunk or Treat Fri 30 Oct 2026, 6:00 PM — Meetup The Church of Jesus Christ of Latter-day Saints · 1958 9th Street Southeast, Winter Haven, FL 33880-4732
SUNDAZE AT KULTURE ON 1ST Sun 1 Nov 2026, 8:00 PM — Meetup KULTURE ON 1ST · 1780 1st Street North, Winter Haven, FL 33881
KARAOKE AT KULTURE ON 1ST Thu 5 Nov 2026, 8:00 PM — Karaoke KULTURE ON 1ST · 1780 1st Street North, Winter Haven, FL 33881
Winter Haven Toastmasters Tue 10 Nov 2026, 6:30 PM — Meetup 656 Ave L NW · 656 Avenue L Northwest, Winter Haven, FL 33881
Jennifer Gable from Funny or Die! Fri 13 Nov 2026, 8:00 PM — Comedy 19 3rd St NW · 19 3rd Street Northwest, Winter Haven, FL 33881
Tony Dabas from TikTok! Sun 15 Nov 2026, 8:00 PM — Comedy 19 3rd St NW · 19 3rd Street Northwest, Winter Haven, FL 33881
Selling Smart in 2026: What Every Polk County Homeowner Needs to Know Sat 21 Nov 2026, 10:00 AM — class 245 W Central Ave suite 101 · 245 West Central Avenue #suite 101, Winter Haven, FL 33880
Listings are seeded from venue and organiser calendars. See them on the map.