40 upcoming listings — live music, theater, markets, drag, comedy and more, each with a time, a venue and a street address.
What's coming up
Her Circle Sunset Walk (The Villages) Wed 26 Aug 2026, 6:30 PM — Meetup Black Lake Walking Path · 1526 Buena Vista Blvd, The Villages, FL 32162
Women’s Game Night (The Villages) Thu 27 Aug 2026, 6:30 PM — Game night Metro Diner · 4110 Wedgewood Lane, The Villages, FL 32162
Sip & Dip Pool Party Sat 29 Aug 2026, 11:00 AM — Live music The Brownwood Hotel & Spa · 3003 Brownwood Boulevard, The Villages, FL 32163
Women’s Sundresses, Sunshine and Duck Brunch (The Villages) Sun 30 Aug 2026, 11:00 AM — Meetup RJ Gator's Florida Sea Grill & Bar · 1015 Lake Shore Drive #1693, The Villages, FL 32162
The Village Vibe: Biz Edition Tue 1 Sep 2026, 9:00 AM — Meetup 1552 Bella Cruz Dr · 1552 Bella Cruz Drive, The Villages, FL 32159
Free Movie for Seniors: The Brink of War Tue 1 Sep 2026, 11:00 AM — Meetup Old Mill Playhouse · 1000 Old Mill Run, The Villages, FL 32162
Free Movie: The Brink of War Tue 1 Sep 2026, 2:00 PM — Meetup Old Mill Playhouse · 1000 Old Mill Run, The Villages, FL 32162 · 18+
Free Dementia with Lewy Bodies Support Group Wed 2 Sep 2026, 3:00 PM — Support group Charter Research · 1025 Lake Sumter Landing, The Villages, FL 32162
Calypso Curated Rum Dinner Thu 3 Sep 2026, 5:30 PM — class Calypso · 1105 Lake Shore Drive, The Villages, FL 32162
First Steps: Living Well with Cognitive Impairment Fri 4 Sep 2026, 10:00 AM — Support group Charter Research · 1025 Lake Sumter Landing, The Villages, FL 32162
LOL in The Villages, FL - Smart-guided Community Bikeway Selfie Tour Sat 5 Sep 2026, 11:00 AM — Meetup CycleNuts Selfie Cycling Tour in The Villages, Florida - Long One-way Loop smart-guided cycling tour · 1000 Lake Sumter Landing, The Villages, FL 32162
CenterWell Lake Deaton Open House Wed 9 Sep 2026, 5:00 PM — class 779 Kristine Way · 779 Kristine Way, The Villages, FL 32163
Free Movie for Seniors: Practical Magic 2 Mon 14 Sep 2026, 11:00 AM — Meetup Old Mill Playhouse Epic Theatres of The Villages · 1000 Old Mill Run, The Villages, FL 32162
Free Movie: Practical Magic 2 Mon 14 Sep 2026, 2:00 PM — Meetup Old Mill Playhouse Epic Theatres of The Villages · 1000 Old Mill Run, The Villages, FL 32162 · 18+
Beauty Beyond the Brush: A masterclass with Celebrity Artist, Shawn Towne Tue 15 Sep 2026, 1:30 PM — class The Brownwood Spa · 3003 Brownwood Boulevard, The Villages, FL 32163
Free Dementia Caregiver Support Group Wed 16 Sep 2026, 3:00 PM — Support group Charter Research · 1025 Lake Sumter Landing, The Villages, FL 32162
Free Lunch & Learn: Understanding Diabetic Neuropathy Thu 17 Sep 2026, 12:00 PM — class Arnold Palmer Legends Country Club · 1635 Palmer Way, The Villages, FL 32162 · 18+
Wine Dinner Series at The Brownwood Hotel & Spa Fri 18 Sep 2026, 5:30 PM — Meetup The Brownwood Hotel & Spa · 3003 Brownwood Boulevard, The Villages, FL 32163
Free for Seniors: Golden Oldies Music Bingo Tue 22 Sep 2026, 3:00 PM — Game night Old Mill Playhouse Epic Theatres of The Villages · 1000 Old Mill Run, The Villages, FL 32162
Free Lunch and Learn: Understanding Fatty Liver Disease Thu 24 Sep 2026, 12:00 PM — class Golden Corral Buffet & Grill · 3950 Wedgewood Lane, The Villages, FL 32162 · 18+
Sip & Dip Pool Party Sat 26 Sep 2026, 11:00 AM — Live music The Brownwood Hotel & Spa · 3003 Brownwood Boulevard, The Villages, FL 32163
Free Movie for Seniors: Avengers: Endgame Encore Mon 28 Sep 2026, 11:00 AM — Meetup Old Mill Playhouse · 1000 Old Mill Run, The Villages, FL 32162
Free Lunch & Learn: Understanding Clinical Trials Tue 29 Sep 2026, 12:00 PM — class Arnold Palmer Legends Country Club · 1635 Palmer Way, The Villages, FL 32162
The Village Vibe: Biz Edition Thu 1 Oct 2026, 9:00 AM — Meetup 1552 Bella Cruz Dr · 1552 Bella Cruz Drive, The Villages, FL 32159
First Steps: Living Well with Cognitive Impairment Fri 2 Oct 2026, 10:00 AM — Support group Charter Research · 1025 Lake Sumter Landing, The Villages, FL 32162
LOL in The Villages, FL - Smart-guided Community Bikeway Selfie Tour Sat 3 Oct 2026, 11:00 AM — Meetup CycleNuts Selfie Cycling Tour in The Villages, Florida - Long One-way Loop smart-guided cycling tour · 1000 Lake Sumter Landing, The Villages, FL 32162
Free Dementia with Lewy Bodies Support Group Wed 7 Oct 2026, 3:00 PM — Support group Charter Research · 1025 Lake Sumter Landing, The Villages, FL 32162
CenterWell Santa Barbara Open House Wed 7 Oct 2026, 5:00 PM — class 1575 Santa Barbara Blvd · 1575 Santa Barbara Boulevard, The Villages, FL 32159
Mid Florida Agencies Florida Blue Presents Celebrating the Blues Wed 14 Oct 2026, 11:00 AM — Live music The Villages Polo Club · 703 Buena Vista Boulevard, The Villages, FL 32162
Diving Deeper Into the Nutrition Label / Sara Gosik Thu 15 Oct 2026, 2:00 PM — class The Villages Health Lake Deaton Care Center · 779 Kristine Way, The Villages, FL 32163
Wine Dinner Series at The Brownwood Hotel & Spa Fri 16 Oct 2026, 5:30 PM — Meetup The Brownwood Hotel & Spa · 3003 Brownwood Boulevard, The Villages, FL 32163
Peter Asher: Songs & Stories@Villages Tue 20 Oct 2026, 7:00 PM — Live music Ezell Recreation Center · 769 Marilee Place, The Villages, FL 32163
Free Dementia Caregiver Support Group Wed 21 Oct 2026, 3:00 PM — Support group Charter Research · 1025 Lake Sumter Landing, The Villages, FL 32162
Sip & Dip Pool Party Sat 24 Oct 2026, 11:00 AM — Live music The Brownwood Hotel & Spa · 3003 Brownwood Boulevard, The Villages, FL 32163
The Village Vibe: Biz Edition Sun 1 Nov 2026, 9:00 AM — Meetup 1552 Bella Cruz Dr · 1552 Bella Cruz Drive, The Villages, FL 32159
Free Dementia with Lewy Bodies Support Group Wed 4 Nov 2026, 3:00 PM — Support group Charter Research · 1025 Lake Sumter Landing, The Villages, FL 32162
First Steps: Living Well with Cognitive Impairment Fri 6 Nov 2026, 10:00 AM — Support group Charter Research · 1025 Lake Sumter Landing, The Villages, FL 32162
LOL in The Villages, FL - Smart-guided Community Bikeway Selfie Tour Sat 7 Nov 2026, 11:00 AM — Meetup CycleNuts Selfie Cycling Tour in The Villages, Florida - Long One-way Loop smart-guided cycling tour · 1000 Lake Sumter Landing, The Villages, FL 32162
FREE Conference for Prostate Cancer Patients & Caregivers Sat 14 Nov 2026, 8:00 AM — Meetup The Brownwood Hotel & Spa · 3003 Brownwood Boulevard, The Villages, FL 32163
Free Dementia Caregiver Support Group Wed 18 Nov 2026, 3:00 PM — Support group Charter Research · 1025 Lake Sumter Landing, The Villages, FL 32162
Listings are seeded from venue and organiser calendars. See them on the map.