Winter holiday events in The Villages, FL

Rollins Mens Lacrosse Winter Prospect Day 2026
Sun, Jan 25, 8:00 AM
Winter park · Rollins College
Rollins Mens Lacrosse Winter Prospect Day 2026
Sun, Jan 25, 8:00 AM
Winter park · Rollins College
Winter Wonderland (All White Affair)
Sun, Dec 21, 12:00 PM
Winter Park · 3377 Aloma Ave
Winter Wonderland (All White Affair)
Sun, Dec 21, 12:00 PM
Winter Park · 3377 Aloma Ave
Sales end soon
A Date Night Adventure! - Feel the Adventure Breeze at Winter Park
Tomorrow at 8:00 AM + 79 more
Winter Park · Peacock Fountain
Sales end soon
A Date Night Adventure! - Feel the Adventure Breeze at Winter Park
Tomorrow at 8:00 AM + 79 more
Winter Park · Peacock Fountain
Winter Drunk Olympics
Sat, Dec 27, 10:00 PM
Orlando · Fixtion Restaurant & Bar
Winter Drunk Olympics
Sat, Dec 27, 10:00 PM
Orlando · Fixtion Restaurant & Bar
SCRUBS SOCIAL
Fri, Dec 5, 7:00 PM
Winter Park · 1685 Lee Rd
SCRUBS SOCIAL
Fri, Dec 5, 7:00 PM
Winter Park · 1685 Lee Rd
Keys of Kindness Holiday Show
Sat, Dec 20, 6:00 PM
Windermere · 1526 Lake Whitney Dr
Keys of Kindness Holiday Show
Sat, Dec 20, 6:00 PM
Windermere · 1526 Lake Whitney Dr
Sales end soon
Get It How You Feel Wednesdays
Wednesday at 8:00 PM
Ocoee · Blu Cafe
Sales end soon
Get It How You Feel Wednesdays
Wednesday at 8:00 PM
Ocoee · Blu Cafe
Just added!
Holiday Candle Making
Sat, Dec 13, 8:00 PM
Lake Mary · Kava Culture Lake Mary (right next to Top Tier)
Just added!
Holiday Candle Making
Sat, Dec 13, 8:00 PM
Lake Mary · Kava Culture Lake Mary (right next to Top Tier)
Polasek Nights – A Holiday Speakeasy
Wed, Dec 10, 6:00 PM
Winter Park · Albin Polasek Museum & Sculpture Gardens
Polasek Nights – A Holiday Speakeasy
Wed, Dec 10, 6:00 PM
Winter Park · Albin Polasek Museum & Sculpture Gardens
10TH Annual Tipsy Elf Holiday Bar Crawl
Tue, Dec 23, 4:30 PM
Mount Dora · Sunset Park
10TH Annual Tipsy Elf Holiday Bar Crawl
Tue, Dec 23, 4:30 PM
Mount Dora · Sunset Park
Holiday Boat Parade Paddle & Toy Drive
Sat, Dec 13, 5:00 PM
Winter Park · Dinky Dock Park
Holiday Boat Parade Paddle & Toy Drive
Sat, Dec 13, 5:00 PM
Winter Park · Dinky Dock Park
Rotaract Holiday Networking
Tue, Dec 2, 5:00 AM
Winter Park · Rollins College
Rotaract Holiday Networking
Tue, Dec 2, 5:00 AM
Winter Park · Rollins College
Holiday Cupcake Decorating Class
Sat, Dec 20, 2:00 PM
Ocala · Soirees & Such
Holiday Cupcake Decorating Class
Sat, Dec 20, 2:00 PM
Ocala · Soirees & Such
24th Annual Unity Heritage Festival MLK Celebration - Vendors Needed
Sun, Jan 18, 11:00 AM
Winter Park · Winter Park Community Center
24th Annual Unity Heritage Festival MLK Celebration - Vendors Needed
Sun, Jan 18, 11:00 AM
Winter Park · Winter Park Community Center
Sales end soon
A Fun-Filled Scavenger Hunt! - Feel the Adventure Breeze at Winter Park
Tomorrow at 8:00 AM + 103 more
Winter Park · Peacock Fountain
Sales end soon
A Fun-Filled Scavenger Hunt! - Feel the Adventure Breeze at Winter Park
Tomorrow at 8:00 AM + 103 more
Winter Park · Peacock Fountain
Just added!
Purpose In Every Season
Sun, Dec 14, 3:30 PM
Leesburg · Artist With A Purpose
Just added!
Purpose In Every Season
Sun, Dec 14, 3:30 PM
Leesburg · Artist With A Purpose
No Doubt Gwen Stefani Holiday Tribute & Toys for Tots at Aloma Cinema Grill
Sun, Dec 14, 6:00 PM
Winter Park · Aloma Cinema Grill
No Doubt Gwen Stefani Holiday Tribute & Toys for Tots at Aloma Cinema Grill
Sun, Dec 14, 6:00 PM
Winter Park · Aloma Cinema Grill
New Years Eve Gala
Wed, Dec 31, 8:00 PM
Dade City · 16117 Lake Iola Rd
New Years Eve Gala
Wed, Dec 31, 8:00 PM
Dade City · 16117 Lake Iola Rd
SANTACON ULTIMATE HOLIDAY BAR CRAWL
Fri, Dec 19, 6:00 PM
Orlando · Blue Martini Lounge Pointe Orlando
SANTACON ULTIMATE HOLIDAY BAR CRAWL
Fri, Dec 19, 6:00 PM
Orlando · Blue Martini Lounge Pointe Orlando
Nexus Network Winter Meetings Mixer!
Mon, Dec 8, 2:00 PM
Lake Buena Vista · Splitsville Luxury Lanes
Nexus Network Winter Meetings Mixer!
Mon, Dec 8, 2:00 PM
Lake Buena Vista · Splitsville Luxury Lanes

Trends in The Villages

Explore more trends

Rollins Mens Lacrosse Winter Prospect Day 2026

Rollins Mens Lacrosse Winter Prospect Day 2026

Winter Wonderland (All White Affair)

Winter Wonderland (All White Affair)

A Date Night Adventure! - Feel the Adventure Breeze at Winter Park

A Date Night Adventure! - Feel the Adventure Breeze at Winter Park

Winter Drunk Olympics

Winter Drunk Olympics

SCRUBS SOCIAL

SCRUBS SOCIAL

Keys of Kindness Holiday Show

Keys of Kindness Holiday Show

Get It How You Feel Wednesdays

Get It How You Feel Wednesdays

Holiday Candle Making

Holiday Candle Making

Polasek Nights – A Holiday Speakeasy

Polasek Nights – A Holiday Speakeasy

10TH Annual Tipsy Elf Holiday Bar Crawl

10TH Annual Tipsy Elf Holiday Bar Crawl

Holiday Boat Parade Paddle & Toy Drive

Holiday Boat Parade Paddle & Toy Drive

Rotaract Holiday Networking

Rotaract Holiday Networking

Holiday Cupcake Decorating Class

Holiday Cupcake Decorating Class

24th Annual Unity Heritage Festival MLK Celebration - Vendors Needed

24th Annual Unity Heritage Festival MLK Celebration - Vendors Needed

A Fun-Filled Scavenger Hunt! - Feel the Adventure Breeze at Winter Park

A Fun-Filled Scavenger Hunt! - Feel the Adventure Breeze at Winter Park

Purpose In Every Season

Purpose In Every Season

No Doubt Gwen Stefani Holiday Tribute & Toys for Tots at Aloma Cinema Grill

No Doubt Gwen Stefani Holiday Tribute & Toys for Tots at Aloma Cinema Grill

New Years Eve Gala

New Years Eve Gala

SANTACON ULTIMATE HOLIDAY BAR CRAWL

SANTACON ULTIMATE HOLIDAY BAR CRAWL

Nexus Network Winter Meetings Mixer!

Nexus Network Winter Meetings Mixer!

Things to do around The Villages

Trends in The Villages

1. Craft shows

2. St vincent de paul

3. New years eve parties

4. Car show in the villages

5. Christmas

6. Thanksgiving event

7. Oldmill playhouse

8. Free movie

9. Charter free movie

10. Free paper shredding

11. Comedy

12. St vincent de paul catholic church