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Downtown Winter Garden Events
Weekly, holiday, and annual flagship events make Downtown the place to be! From “Friday’s on the Plaza” live musical performances, Saturday Farmers Market; to the annual Spring Fever in the Garden, Halloween Experience, Shop Small Business Saturday, and month-long ‘Tis the Season events — there is always something happening Downtown!
August 2021
Art Exhibition “Unconventional Beauty” Opening Reception
Thursday, August 5
5:30 pm - 8:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio 127 S. Boyd Street
Art Exhibition “Unconventional Beauty”
Friday, August 6
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio 127 S. Boyd Street
Fridays on the Plaza
Friday, August 6
7:00 pm - 9:00 pm
Tree Frogs (Classic Hits - 70’s & 80’s)
Downtown Winter Garden, Centennial Plaza Gazebo
Winter Garden Farmers Market
Saturday, August 7
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Art Exhibition “Unconventional Beauty”
Saturday, August 7
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio 127 S. Boyd Street
Garden Theatre Interactive Movie: The Birdcage
Sunday, August 8
7:00 pm
Garden Theatre 160 West Plant Street
Art Exhibition “Unconventional Beauty”
Tuesday, August 10
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio 127 S. Boyd Street
Art Exhibition “Unconventional Beauty”
Wednesday, August 11
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio 127 S. Boyd Street
Art Exhibition “Unconventional Beauty”
Thursday, August 12
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio 127 S. Boyd Street
Art Exhibition “Unconventional Beauty”
Friday, August 13
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio 127 S. Boyd Street
Fridays on the Plaza
Friday, August 13
7:00 pm - 9:00 pm
Molly Holton (Acoustic Blues)
Downtown Winter Garden, Centennial Plaza Gazebo
Winter Garden Farmers Market
Saturday, August 14
12:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Art Exhibition “Unconventional Beauty”
Saturday, August 14
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio 127 S. Boyd Street
Art Exhibition “Unconventional Beauty”
Tuesday, August 17
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio 127 S. Boyd Street
Art Exhibition “Unconventional Beauty”
Wednesday, August 18
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio 127 S. Boyd Street
Art Exhibition “Unconventional Beauty”
Thursday, August 19
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio 127 S. Boyd Street
Art Exhibition “Unconventional Beauty”
Friday, August 20
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio 127 S. Boyd Street
Fridays on the Plaza
Friday, August 20
7:00 pm - 9:00 pm
Porchdogs (Cajun, Zydeco)
Downtown Winter Garden, Centennial Plaza Gazebo
Winter Garden Farmers Market
Saturday, August 21
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Art Exhibition “Unconventional Beauty”
Saturday, August 21
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio 127 S. Boyd Street
Art Exhibition “Unconventional Beauty”
Tuesday, August 24
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio 127 S. Boyd Street
Art Exhibition “Unconventional Beauty”
Wednesday, August 25
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio 127 S. Boyd Street
Art Exhibition “Unconventional Beauty”
Thursday, August 26
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio 127 S. Boyd Street
Art Exhibition “Unconventional Beauty”
Friday, August 27
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio 127 S. Boyd Street
Fridays on the Plaza
Friday, August 27
7:00 pm - 9:00 pm
Crenshaw (Folk)
Downtown Winter Garden, Centennial Plaza Gazebo
Garden Theatre Play: Man of La Mancha
Friday, August 27
7:30 pm
Preview
Garden Theatre 160 West Plant Street
Winter Garden Farmers Market
Saturday, August 28
8:00 am
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Art Exhibition “Unconventional Beauty”
Saturday, August 28
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio 127 S. Boyd Street
Garden Theatre Play: Man of La Mancha
Saturday, August 28
2:00 pm
Preview
Garden Theatre 160 West Plant Street
Garden Theatre Play: Man of La Mancha
Saturday, August 28
7:30 pm
Opening Night
Garden Theatre 160 West Plant Street
Garden Theatre Play: Man of La Mancha
Sunday, August 29
2:00 pm
Garden Theatre 160 West Plant Street
September 2021
Art Exhibition “For the Love of Trees”
Wednesday, September 1
8:00 am - 5:00 pm
Art in Public Places Gallery, City Hall 300 W. Plant Street
Art Exhibition “Unconventional Beauty”
Wednesday, September 1
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio 127 S. Boyd Street
Art Exhibition “For the Love of Trees”
Thursday, September 2
8:00 am - 5:00 pm
Art in Public Places Gallery, City Hall 300 W. Plant Street
Art Exhibition “Unconventional Beauty”
Thursday, September 2
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio 127 S. Boyd Street
Garden Theatre Play: Man of La Mancha
Thursday, September 2
2:00 pm
Garden Theatre 160 West Plant Street
Garden Theatre Play: Man of La Mancha
Thursday, September 2
7:30 pm
Talkback Performance
Garden Theatre 160 West Plant Street
Art Exhibition “For the Love of Trees”
Friday, September 3
8:00 am - 5:00 pm
Art in Public Places Gallery, City Hall 300 W. Plant Street
Art Exhibition “Unconventional Beauty”
Friday, September 3
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio 127 S. Boyd Street
Fridays on the Plaza
Friday, September 3
7:00 pm - 9:00 pm
Jade Frances (Pop, Acoustic)
Downtown Winter Garden, Centennial Plaza Gazebo
Garden Theatre Play: Man of La Mancha
Friday, September 3
7:30 pm
Garden Theatre 160 West Plant Street
Winter Garden Farmers Market
Saturday, September 4
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Art Exhibition “Unconventional Beauty”
Saturday, September 4
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio 127 S. Boyd Street
Garden Theatre Play: Man of La Mancha
Saturday, September 4
2:00 pm
Garden Theatre 160 West Plant Street
Garden Theatre Play: Man of La Mancha
Saturday, September 4
7:30 pm
Garden Theatre 160 West Plant Street
Garden Theatre Play: Man of La Mancha
Sunday, September 5
2:00 pm
Garden Theatre 160 West Plant Street
Garden Theatre Rewind Movie: Lost in La Mancha
Sunday, September 5
6:30 pm
Garden Theatre 160 West Plant Street
Art Exhibition “For the Love of Trees”
Tuesday, September 7
8:00 am - 5:00 pm
Art in Public Places Gallery, City Hall 300 W. Plant Street
Art Exhibition “Unconventional Beauty”
Tuesday, September 7
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio 127 S. Boyd Street
Art Exhibition “For the Love of Trees”
Wednesday, September 8
8:00 am - 5:00 pm
Art in Public Places Gallery, City Hall 300 W. Plant Street
Remembrance 9-11 Tribute Exhibit at City Hall
Wednesday, September 8
10:00 am - 5:00 pm
City Hall, 300 West Plant Street
Art Exhibition “Unconventional Beauty”
Wednesday, September 8
10:00 pm - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio 127 S. Boyd Street
Art Exhibition “For the Love of Trees”
Thursday, September 9
8:00 am - 5:00 pm
Art in Public Places Gallery, City Hall 300 W. Plant Street
Art Exhibition “Unconventional Beauty”
Thursday, September 9
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio 127 S. Boyd Street
Remembrance 9-11 Tribute Exhibit at City Hall
Thursday, September 9
10:00 am - 8:00 pm
City Hall, 300 West Plant Street
Garden Theatre Play: Man of La Mancha
Thursday, September 9
2:00 pm
Garden Theatre 160 West Plant Street
Garden Theatre Play: Man of La Mancha
Thursday, September 9
7:30 pm
ASL Interpreted Performance
Garden Theatre 160 West Plant Street
Art Exhibition “For the Love of Trees”
Friday, September 10
8:00 am - 5:00 pm
Art in Public Places Gallery, City Hall 300 W. Plant Street
Art Exhibition “Unconventional Beauty”
Friday, September 10
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio 127 S. Boyd Street
Remembrance 9-11 Tribute Exhibit at City Hall
Friday, September 10
10:00 am - 8:00 pm
City Hall, 300 West Plant Street
Fridays on the Plaza
Friday, September 10
7:00 pm - 9:00 pm
Grimes Alley (Blues, Country, Acoustic)
Downtown Winter Garden, Centennial Plaza Gazebo
Garden Theatre Play: Man of La Mancha
Friday, September 10
7:30 pm
Garden Theatre 160 West Plant Street
Winter Garden Farmers Market
Saturday, September 11
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Remembrance 9-11 Tribute Exhibit at City Hall
Saturday, September 11
10:00 am - 3:00 pm
City Hall, 300 West Plant Street
Art Exhibition “Unconventional Beauty”
Saturday, September 11
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio 127 S. Boyd Street
Garden Theatre Play: Man of La Mancha
Saturday, September 11
2:00 pm
Garden Theatre 160 West Plant Street
Garden Theatre Play: Man of La Mancha
Saturday, September 11
7:30 pm
Garden Theatre 160 West Plant Street
Garden Theatre Play: Man of La Mancha
Sunday, September 12
2:00 pm
Garden Theatre 160 West Plant Street
Garden Theatre Interactive Movie: Clue
Sunday, September 12
7:00 pm
Garden Theatre 160 West Plant Street
Art Exhibition “For the Love of Trees”
Monday, September 13
8:00 am - 5:00 pm
Art in Public Places Gallery, City Hall 300 W. Plant Street
Art Exhibition “For the Love of Trees”
Tuesday, September 14
8:00 am - 5:00 pm
Art in Public Places Gallery, City Hall 300 W. Plant Street
Art Exhibition “Unconventional Beauty”
Tuesday, September 14
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio 127 S. Boyd Street
Art Exhibition “For the Love of Trees”
Wednesday, September 15
8:00 am - 5:00 pm
Art in Public Places Gallery, City Hall 300 W. Plant Street
Art Exhibition “Unconventional Beauty”
Wednesday, September 15
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio 127 S. Boyd Street
Art Exhibition “For the Love of Trees”
Thursday, September 16
8:00 am - 5:00 pm
Art in Public Places Gallery, City Hall 300 W. Plant Street
Art Exhibition “Unconventional Beauty”
Thursday, September 16
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio 127 S. Boyd Street
Garden Theatre Play: Man of La Mancha
Thursday, September 16
7:30 pm
Garden Theatre 160 West Plant Street
Art Exhibition “For the Love of Trees”
Friday, September 17
8:00 am - 5:00 pm
Art in Public Places Gallery, City Hall 300 W. Plant Street
Art Exhibition “Unconventional Beauty”
Friday, September 17
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio 127 S. Boyd Street
Hispanic Heritage Month Live Music Performance
Friday, September 17
7:00 pm - 9:00 pm
Don Soledad (Flamenco)
Downtown Winter Garden, Centennial Plaza Gazebo
Garden Theatre Play: Man of La Mancha
Friday, September 17
7:30 pm
Garden Theatre 160 West Plant Street
Winter Garden Farmers Market
Saturday, September 18
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Create Hispanic Heritage Art at the Farmers Market
Saturday, September 18
9:00 am - 12:00 pm
Downtown Pavilion, 104 S. Lakeview Avenue
Art Exhibition “Unconventional Beauty”
Saturday, September 18
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio 127 S. Boyd Street
Garden Theatre Play: Man of La Mancha
Saturday, September 18
2:00 pm
Garden Theatre 160 West Plant Street
OCLS – Virtual Event: Hispanic Heritage Livestream
Saturday, September 18
4:00 pm
Music Sensation Sonia De Los Santos
Orange County Library Winter Garden Branch, 805 E. Plant St.
Garden Theatre Play: Man of La Mancha
Saturday, September 18
7:30 pm
Garden Theatre 160 West Plant Street
Garden Theatre Play: Man of La Mancha
Sunday, September 19
2:00 pm
Garden Theatre 160 West Plant Street
Art Exhibition “For the Love of Trees”
Monday, September 20
8:00 am - 5:00 pm
Art in Public Places Gallery, City Hall 300 W. Plant Street
OCLS – Virtual Event: Hispanic Heritage Month – Mexican Folk Art
Monday, September 20
6:00 pm
Create your own craft honoring Mexican Folk Art
Orange County Library Winter Garden Branch, 805 E. Plant St.
Art Exhibition “For the Love of Trees”
Tuesday, September 21
8:00 am - 5:00 pm
Art in Public Places Gallery, City Hall 300 W. Plant Street
Art Exhibition “Unconventional Beauty”
Tuesday, September 21
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio 127 S. Boyd Street
Art Exhibition “For the Love of Trees”
Wednesday, September 22
8:00 am - 5:00 pm
Art in Public Places Gallery, City Hall 300 W. Plant Street
Art Exhibition “Unconventional Beauty”
Wednesday, September 22
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio 127 S. Boyd Street
Driftwood Market – Artisan Workshop – Halloween Witches Hat
Wednesday, September 22
6:00 pm - 8:00 pm
46 W Plant St
Art Exhibition “For the Love of Trees”
Thursday, September 23
8:00 am - 5:00 pm
Art in Public Places Gallery, City Hall 300 W. Plant Street
Art Exhibition “Unconventional Beauty”
Thursday, September 23
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio 127 S. Boyd Street
OCLS – Virtual Event: Hispanic Heritage Month – Meet the Authors
Thursday, September 23
7:00 pm
Celebrate with this author panel
Orange County Library Winter Garden Branch, 805 E. Plant St.
Art Exhibition “For the Love of Trees”
Friday, September 24
8:00 am - 5:00 pm
Art in Public Places Gallery, City Hall 300 W. Plant Street
Art Exhibition “Unconventional Beauty”
Friday, September 24
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio 127 S. Boyd Street
Driftwood Market – Artisan Workshop – Scarecrow Wreath Class
Friday, September 24
6:00 pm - 8:00 pm
46 W Plant St
Hispanic Heritage Month Live Music Performance
Friday, September 24
7:00 pm - 9:00 pm
Mariachi Internacional Tapatio 4-Piece Band
Downtown Winter Garden, Centennial Plaza Gazebo
Winter Garden Farmers Market
Saturday, September 25
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Hispanic Heritage Month Art Class -Mexican Bark Painting
Saturday, September 25
9:00 am - 10:00 am
Mexican Bark Painting - $15.00 (Members: $3 discount per session) - Materials included
SOBO Art Gallery & Studio, 127 S. Boyd Street
Hispanic Heritage Month Live Music at Farmers Market
Saturday, September 25
10:00 am - 1:00 pm
Flamenco Tropical and Jessica Pacheco (Classical Spanish, Flamenco, Gipsy Rumba)
Downtown Pavilion, 104 S. Lakeview Avenue
Art Exhibition “Unconventional Beauty”
Saturday, September 25
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio 127 S. Boyd Street
Hispanic Heritage Month Art Class – Pottery Painting
Saturday, September 25
10:15 am - 11:15 am
Pottery Painting - $20.00 (Members: $3 discount per session) - Materials included
SOBO Art Gallery & Studio, 127 S. Boyd Street
Hispanic Heritage Month Art Class – Foil Art
Saturday, September 25
11:30 am - 12:30 pm
Foil Art - $15.00 (Members: $3 discount per session) - Materials included
SOBO Art Gallery & Studio, 127 S. Boyd Street
Art Exhibition “For the Love of Trees”
Monday, September 27
8:00 am - 5:00 pm
Art in Public Places Gallery, City Hall 300 W. Plant Street
Driftwood Market – Artisan Workshop – Scarecrow Wreath Class
Monday, September 27
6:00 pm - 8:00 pm
46 W Plant St
Art Exhibition “For the Love of Trees”
Tuesday, September 28
8:00 am - 5:00 pm
Art in Public Places Gallery, City Hall 300 W. Plant Street
Art Exhibition “Unconventional Beauty”
Tuesday, September 28
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio 127 S. Boyd Street
Driftwood Market – Artisan Workshop – Easy, Fun Candle Making
Tuesday, September 28
6:00 pm
46 W Plant St
Art Exhibition “For the Love of Trees”
Wednesday, September 29
8:00 am - 5:00 pm
Art in Public Places Gallery, City Hall 300 W. Plant Street
Art Exhibition “Unconventional Beauty”
Wednesday, September 29
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio 127 S. Boyd Street
Driftwood Market – Artisan Workshop – Halloween Decor Class
Wednesday, September 29
6:00 pm - 9:00 pm
46 W Plant St
Art Exhibition “For the Love of Trees”
Thursday, September 30
8:00 am - 5:00 pm
Art in Public Places Gallery, City Hall 300 W. Plant Street
Art Exhibition “Unconventional Beauty”
Thursday, September 30
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio 127 S. Boyd Street
October 2021
Art Exhibition: “The Art of Mentorship IV” presented by Crealdé School of Art.
Friday, October 1
7:30 am - 5:30 pm
Art in Public Places Gallery, City Hall 300 W. Plant Street
Art Exhibition “Unconventional Beauty”
Friday, October 1
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio 127 S. Boyd Street
Driftwood Market – Artisan Workshop – Fall/Halloween Watercolor
Friday, October 1
1:30 pm - 4:30 pm
46 W Plant St
Fridays on the Plaza
Friday, October 1
7:00 pm - 9:00 pm
Sandy Back Porch (Bluegrass)
Downtown Winter Garden, Centennial Plaza Gazebo
Winter Garden Farmers Market
Saturday, October 2
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Driftwood Market – Pop Up Event – Sonja Jeanette Handmade Jewelry
Saturday, October 2
10:00 am - 3:00 pm
46 W Plant St
Art Exhibition “Unconventional Beauty”
Saturday, October 2
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio 127 S. Boyd Street
Driftwood Market – A Taste of Fall
Saturday, October 2
11:00 am - 3:00 pm
Free Event - RSVP Required
46 W Plant St
Art Exhibition: “The Art of Mentorship IV” presented by Crealdé School of Art.
Monday, October 4
7:30 am - 5:30 pm
Art in Public Places Gallery, City Hall 300 W. Plant Street
Art Exhibition: “The Art of Mentorship IV” presented by Crealdé School of Art.
Tuesday, October 5
7:30 am - 5:30 pm
Art in Public Places Gallery, City Hall 300 W. Plant Street
Art Exhibition: “The Art of Mentorship IV” presented by Crealdé School of Art.
Wednesday, October 6
7:30 am - 5:30 pm
Art in Public Places Gallery, City Hall 300 W. Plant Street