28 upcoming listings — live music, theater, markets, drag, comedy and more, each with a time, a venue and a street address.
What's coming up
SUNDAZE AT KULTURE ON 1ST Sun 4 Oct 2026, 8:00 PM — Meetup KULTURE ON 1ST · 1780 1st Street North, Winter Haven, FL 33881
Ginger Kelly & Friends! Thu 8 Oct 2026, 8:00 PM — Comedy 19 3rd St NW · 19 3rd Street Northwest, Winter Haven, FL 33881
KARAOKE AT KULTURE ON 1ST Thu 8 Oct 2026, 8:00 PM — Karaoke 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
Adam Snair & Friends! Thu 15 Oct 2026, 8:00 PM — Comedy 19 3rd St NW · 19 3rd Street 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
Jada Fish Live Sat 17 Oct 2026, 10:00 PM — Live music 2862 Recker Hwy · 2862 Recker Highway, Winter Haven, FL 33880
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
Smile City Comedy Show! with Rob Smiles Thu 29 Oct 2026, 8:00 PM — Comedy 19 3rd St NW · 19 3rd Street 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
Halloween Comedy and Costume Contest with Dick Ruse! Fri 30 Oct 2026, 8:00 PM — Comedy 19 3rd St NW · 19 3rd Street Northwest, Winter Haven, FL 33881
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
Work Sucks: A Comedy Showcase! Thu 12 Nov 2026, 8:00 PM — Comedy 19 3rd St NW · 19 3rd Street 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
Celebrating 25 years - Tantric brings their anniversary tour to Jessie’s Wed 18 Nov 2026, 5:00 PM — Live music Jessie's · 118 3rd Street Southwest, Winter Haven, FL 33880
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
Paralandra & Major Moment join forces for Florida tour coming to Jessies Tue 8 Dec 2026, 5:00 PM — Live music Jessie's · 118 3rd Street Southwest, Winter Haven, FL 33880
Lisa RodDavis & Friends! Thu 10 Dec 2026, 8:00 PM — Comedy 19 3rd St NW · 19 3rd Street Northwest, Winter Haven, FL 33881
Listings are seeded from venue and organiser calendars. See them on the map.