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June Events and Things to do in Winter Park, FL

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
Father's Day 2026 Aboard the Barbara Lee
Sun, Jun 21, 11:30 AM
Sanford · St Johns Rivership Company
Father's Day 2026 Aboard the Barbara Lee
Sun, Jun 21, 11:30 AM
Sanford · St Johns Rivership Company
Everybody ❤️’s Alchemy Saturdays
Sat, Jun 6, 10:00 PM + 3 more
Orlando · Alchemy Lounge
Everybody ❤️’s Alchemy Saturdays
Sat, Jun 6, 10:00 PM + 3 more
Orlando · Alchemy Lounge
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
Going fast
Bonsai & Cheers at Home State Brewing | Dwarf Jade Bonsai Workshop
Sat, Jun 6, 11:30 AM
Winter Garden · Home State Brewing Co.
Going fast
Bonsai & Cheers at Home State Brewing | Dwarf Jade Bonsai Workshop
Sat, Jun 6, 11:30 AM
Winter Garden · Home State Brewing Co.
Seasonal Tasting Series: BBQ (Clermont)
Sat, Jun 27, 6:30 PM
Winter Garden · 4 Rivers Smokehouse
Seasonal Tasting Series: BBQ (Clermont)
Sat, Jun 27, 6:30 PM
Winter Garden · 4 Rivers Smokehouse
Juneteenth: The Skip Day & Brunch!
Fri, Jun 19, 12:00 PM
Orlando · Reflections at Glasshouse
Juneteenth: The Skip Day & Brunch!
Fri, Jun 19, 12:00 PM
Orlando · Reflections at Glasshouse
Citrus Aroma - Paint and Sip in Orlando | Classpop!™
Wed, Jun 3, 6:00 PM
Orlando · World of Beer
Citrus Aroma - Paint and Sip in Orlando | Classpop!™
Wed, Jun 3, 6:00 PM
Orlando · World of Beer
Yoga & Beer
Sun, Jun 21, 10:00 AM
Winter Garden · Crooked Can Brewing Company
Yoga & Beer
Sun, Jun 21, 10:00 AM
Winter Garden · Crooked Can Brewing Company
Just added
Boards and bouquets
Sat, Jun 6, 11:30 AM
Orlando · Magical Charcuterie
Just added
Boards and bouquets
Sat, Jun 6, 11:30 AM
Orlando · Magical Charcuterie
UNO Winter Garden Dad and Me Detroit Style Pizza Cooking Class
Sat, Jun 20, 12:00 PM
Winter Garden · UNO Pizzeria & Grill
UNO Winter Garden Dad and Me Detroit Style Pizza Cooking Class
Sat, Jun 20, 12:00 PM
Winter Garden · UNO Pizzeria & 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
Emotions Fun Day by Mrs. Chakra
Sat, Jun 13, 1:00 PM
Orlando · Sheraton Vistana Villages
Emotions Fun Day by Mrs. Chakra
Sat, Jun 13, 1:00 PM
Orlando · Sheraton Vistana Villages
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
Just added
4th of July Paint and Sip Workshop
Thu, Jun 18, 7:00 PM
Orlando · Curious Cork Wine & Provisions
Just added
4th of July Paint and Sip Workshop
Thu, Jun 18, 7:00 PM
Orlando · Curious Cork Wine & Provisions
June Curious Cork Paint Nite
Thu, Jun 25, 6:00 PM
Orlando · Curious Cork Wine & Provisions
June Curious Cork Paint Nite
Thu, Jun 25, 6:00 PM
Orlando · Curious Cork Wine & Provisions
Comedian Rauce Padgett X Redtail Country Club
Sat, Jun 6, 6:00 PM
Sorrento · Hawk's Bar & Grill at RedTail
Comedian Rauce Padgett X Redtail Country Club
Sat, Jun 6, 6:00 PM
Sorrento · Hawk's Bar & Grill at RedTail
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

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