What are the top Entertainment events happening in Winter Springs?

Here are the top Entertainment events in Winter Springs: Brian Smalley House Concert in Winter Springs, FL is happening on Sat 07 Feb 2026 from 7:00 PM onwards at Winter Spring, Fl, Winter Springs Rabbi Neely's Sweet Sixteen Celebration is happening on Sun 22 Feb 2026 from 5:00 PM onwards at 50 S Moss Rd, Winter Springs, FL, United States, Florida 32708

Winter Springs Entertainment Events

Entertainment events in Winter Springs

Sat, 07 Feb, 2026 - 07:00 PM

Brian Smalley House Concert in Winter Springs, FL

Winter Spring, Fl

12+ Interested
Sun, 22 Feb, 2026 - 05:00 PM

Rabbi Neely's Sweet Sixteen Celebration

50 S Moss Rd, Winter Springs, FL, United States, Florida 32708

11+ Interested

Entertainment events from nearby cities

Featured

Sat, 14 Mar • 07:30 PM

🎸❤️TOTALLY TOM PETTY LAS VEGAS SHOW in FLORIDA - SAT March 14, 2026

Mount Dora Music Hall

87+ Interested

|

USD 37
Sat, 14 Feb Onwards

Sip, Stroke & Whine Paint Party

Napasorn Thai Restaurant

19+ Interested

|

Free
Featured

Sun, 25 Jan • 11:00 AM

Build Your Own Air Purifying Container Garden Class

Dobro's Restaurant

18+ Interested

|

USD 25
Sat, 14 Feb • 06:00 PM

HOOKAHS & HEARTS

Inez Patricia School of Dance

Newly Added

|

USD 175
Sat, 14 Feb • 03:30 PM

Lover's & Friends Bahamas Cruise 2026

Port Canaveral

86+ Interested

|

USD 50
Thu, 22 Jan Onwards

Kissimmee Scavenger Hunt For Couples - SHOW LOVE (Date Night!!)

Recommended scavenger starting point or other city spot of your choice! (YOU MUST USE PDF TICKETS EMAILED FOR EVENT- NO MOBILE APP OR QR CODES ACCEPTED)

Newly Added

|

USD 10
Thu, 22 Jan Onwards

Clermont Scavenger Hunt For Couples - SHOW LOVE (Date Night!!)

Recommended scavenger starting point or other city spot of your choice! (YOU MUST USE PDF TICKETS EMAILED FOR EVENT- NO MOBILE APP OR QR CODES ACCEPTED)

Newly Added

|

USD 10
Sat, 28 Mar • 06:30 PM

80's and Beyond Sing Along and Costume Night - Ticket link in info, this is not a free event.

Old Mill Playhouse Epic Theatres of The Villages

9+ Interested

|

Free
Sun, 15 Feb Onwards

Daytona 500 - NASCAR Cup Series

Daytona International Speedway