June Events and Things to do in Winter Park, FL
Orlando Comedy Club – Stand-Up Comedy on I-Drive
Wed, Jun 3, 8:00 PM + 3 more
Orlando · 6300 Parc Corniche Dr
Orlando Comedy Club – Stand-Up Comedy on I-Drive
Wed, Jun 3, 8:00 PM + 3 more
Orlando · 6300 Parc Corniche Dr
Foodies + New Friends: Orlando | Photographers Edition
Tue, Jun 30, 7:00 PM
Orlando · Restaurant of the Week
Foodies + New Friends: Orlando | Photographers Edition
Tue, Jun 30, 7:00 PM
Orlando · Restaurant of the Week
Weekends in Winter Garden: Foodies + New Friends
Sun, Jun 7, 7:00 PM + 3 more
Winter Garden · Restaurant of the Weekend
Weekends in Winter Garden: Foodies + New Friends
Sun, Jun 7, 7:00 PM + 3 more
Winter Garden · Restaurant of the Weekend
Downton Abbey Themed High Tea Cruise Aboard the Barbara Lee
Tue, Jun 2, 11:30 AM + 3 more
Sanford · St Johns Rivership Company
Downton Abbey Themed High Tea Cruise Aboard the Barbara Lee
Tue, Jun 2, 11:30 AM + 3 more
Sanford · St Johns Rivership Company
Rocking on the River w/ Megan Gunn Aboard the Barbara Lee
Fri, Jun 5, 6:00 PM
Sanford · St Johns Rivership Company
Rocking on the River w/ Megan Gunn Aboard the Barbara Lee
Fri, Jun 5, 6:00 PM
Sanford · St Johns Rivership Company
Rocking on the River - Beetles Tribute w/ John Babcock Aboard the B-Lee
Fri, Jun 12, 6:30 PM
Sanford · St Johns Rivership Company
Rocking on the River - Beetles Tribute w/ John Babcock Aboard the B-Lee
Fri, Jun 12, 6:30 PM
Sanford · St Johns Rivership Company
Orlando Comedy Showcase | Live Comedy at Orlando Comedy Club
Mon, Jun 22, 8:00 PM
Orlando · Calypso Bar & Grill
Orlando Comedy Showcase | Live Comedy at Orlando Comedy Club
Mon, Jun 22, 8:00 PM
Orlando · Calypso Bar & Grill
Bonsai & Cheers -Home State Brewing - L&J Nursery - Dwarf Jade Bonsai
Sat, Jun 6, 11:30 AM
Winter Garden · Home State Brewing Co.
Bonsai & Cheers -Home State Brewing - L&J Nursery - Dwarf Jade Bonsai
Sat, Jun 6, 11:30 AM
Winter Garden · Home State Brewing Co.
Stand-Up Comedy Night in Orlando: Nadeem Awaad & David Sadman
Fri, Jun 26, 8:00 PM
Orlando · Calypso Bar & Grill
Stand-Up Comedy Night in Orlando: Nadeem Awaad & David Sadman
Fri, Jun 26, 8:00 PM
Orlando · Calypso Bar & Grill
Buffet Dinner Aboard the Barbara Lee
Wed, Jun 3, 6:00 PM + 3 more
Sanford · St Johns Rivership Company
Buffet Dinner Aboard the Barbara Lee
Wed, Jun 3, 6:00 PM + 3 more
Sanford · St Johns Rivership Company
Let’s Play! Trivia, Bingo & Game Show Night Cruise Aboard the Barbara Lee
Fri, Jun 19, 6:30 PM
Sanford · St Johns Rivership Company
Let’s Play! Trivia, Bingo & Game Show Night Cruise Aboard the Barbara Lee
Fri, Jun 19, 6:30 PM
Sanford · St Johns Rivership Company
Four Seasons Orlando Resort: Oasis Sundays
Sun, Jun 7, 11:00 AM + 1 more
Lake Buena Vista · Four Seasons Resort Orlando at Walt Disney World® Resort
Four Seasons Orlando Resort: Oasis Sundays
Sun, Jun 7, 11:00 AM + 1 more
Lake Buena Vista · Four Seasons Resort Orlando at Walt Disney World® Resort
Main Street PD 2026: Practical Strategies Educators Can Use
Mon, Jun 15, 8:00 AM
Lake Buena Vista · Wyndham Lake Buena Vista Disney Springs Resort Area
Main Street PD 2026: Practical Strategies Educators Can Use
Mon, Jun 15, 8:00 AM
Lake Buena Vista · Wyndham Lake Buena Vista Disney Springs Resort Area
GIW aka Girls in Wonderland- Orlando 2026 - Tickets Only
Thu, Jun 4, 1:00 PM
Winter Garden · SPRINGHILL SUITES and TOWNEPLACE SUITES
GIW aka Girls in Wonderland- Orlando 2026 - Tickets Only
Thu, Jun 4, 1:00 PM
Winter Garden · SPRINGHILL SUITES and TOWNEPLACE SUITES
GIW Orlando / Passes June 4–8, 2026 Girls in Wonderland
Thu, Jun 4, 10:00 AM
Winter Garden · SPRINGHILL SUITES & TOWNEPLACE SUITES
GIW Orlando / Passes June 4–8, 2026 Girls in Wonderland
Thu, Jun 4, 10:00 AM
Winter Garden · SPRINGHILL SUITES & TOWNEPLACE SUITES
