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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!
December 2021
Art Exhibition: There’s a Map for That! Find Your Way Home: A Cartographic Survey of West Orange County
Wednesday, December 1
7:30 am - 5:30 pm
Curated by the Winter Garden Heritage Foundation
Art in Public Places Gallery in City Hall, 300 W. Plant Street
Art Exhibition: “Fun and/or Functional”
Wednesday, December 1
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street
Art Exhibition: There’s a Map for That! Find Your Way Home: A Cartographic Survey of West Orange County
Thursday, December 2
7:30 am - 5:30 pm
Curated by the Winter Garden Heritage Foundation
Art in Public Places Gallery in City Hall, 300 W. Plant Street
Art Exhibition: “Fun and/or Functional”
Thursday, December 2
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street
Garden Theatre Play: Big, The Musical
Thursday, December 2
2:00 pm
Garden Theatre, 160 West Plant Street
Art Exhibition “Fun…and/or Functional” Opening Reception
Thursday, December 2
5:30 pm - 8:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio 127 S. Boyd Street
Driftwood Market – Artisan Workshop – Couch Cuddle Blanket
Thursday, December 2
6:00 pm - 8:00 pm
46 W Plant St
Garden Theatre Play: Big, The Musical
Thursday, December 2
7:30 pm
ASL Interpreted Performance
Garden Theatre, 160 West Plant Street
Art Exhibition: There’s a Map for That! Find Your Way Home: A Cartographic Survey of West Orange County
Friday, December 3
7:30 am - 5:30 pm
Curated by the Winter Garden Heritage Foundation
Art in Public Places Gallery in City Hall, 300 W. Plant Street
Art Exhibition: “Fun and/or Functional”
Friday, December 3
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street
A Merry Winter Garden Light Show
Friday, December 3
6:00 pm - 9:00 pm
City Hall, 300 W. Plant St.
Light Up Winter Garden
Friday, December 3
6:00 pm - 9:00 pm
Tree Lighting at 6:15 pm
Downtown Winter Garden, 300 W. Plant Street
Winter Garden First Baptist Holiday Concert
Friday, December 3
6:30 pm
On the steps of Winter Garden First Baptist Church, 125 E. Plant St
Garden Theatre Play: Big, The Musical
Friday, December 3
7:30 pm
Garden Theatre, 160 West Plant Street
Pilars – Visiting Artist Series
Friday, December 3
8:00 pm - 11:00 pm
Hammondimonium! with Ed Krout, Susy Park, Joe Breidenstine, & Walt Hubbard
146 W Plant St
Art Exhibition: “Fun and/or Functional”
Saturday, December 4
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street
Winter Garden Christmas Parade
Saturday, December 4
10:00 am
Kick off from S. Dillard Street and E. Plant Street
Garden Theatre Play: Big, The Musical
Saturday, December 4
2:00 pm
Garden Theatre, 160 West Plant Street
Horse Drawn Holiday Carriage Tours
Saturday, December 4
5:30 pm - 9:30 pm
Downtown Pavilion, 104 S. Lakeview Avenue
A Merry Winter Garden Light Show
Saturday, December 4
6:00 pm - 9:00 pm
City Hall, 300 W. Plant St.
Garden Theatre Play: Big, The Musical
Saturday, December 4
7:30 pm
Garden Theatre, 160 West Plant Street
Pilars – Visiting Artist Series
Saturday, December 4
8:00 pm - 11:00 pm
Ron Jenkins, Per & Tamara Danielsson
146 W Plant St
Garden Theatre Play: Big, The Musical
Sunday, December 5
2:00 pm
Garden Theatre, 160 West Plant Street
Garden Theatre Interactive Movie: The Muppet Christmas Carol
Sunday, December 5
7:00 pm
Garden Theatre 160 West Plant Street
Art Exhibition: There’s a Map for That! Find Your Way Home: A Cartographic Survey of West Orange County
Monday, December 6
7:30 am - 5:30 pm
Curated by the Winter Garden Heritage Foundation
Art in Public Places Gallery in City Hall, 300 W. Plant Street
Art Exhibition: There’s a Map for That! Find Your Way Home: A Cartographic Survey of West Orange County
Tuesday, December 7
7:30 am - 5:30 pm
Curated by the Winter Garden Heritage Foundation
Art in Public Places Gallery in City Hall, 300 W. Plant Street
Art Exhibition: “Fun and/or Functional”
Tuesday, December 7
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street
SOBO Art Gallery: Technique Tuesdays at 2pm
Tuesday, December 7
2:00 pm
"Collage" Allison Dyer
Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street
Art Exhibition: There’s a Map for That! Find Your Way Home: A Cartographic Survey of West Orange County
Wednesday, December 8
7:30 am - 5:30 pm
Curated by the Winter Garden Heritage Foundation
Art in Public Places Gallery in City Hall, 300 W. Plant Street
Art Exhibition: “Fun and/or Functional”
Wednesday, December 8
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street
Art Exhibition: There’s a Map for That! Find Your Way Home: A Cartographic Survey of West Orange County
Thursday, December 9
7:30 am - 5:30 pm
Curated by the Winter Garden Heritage Foundation
Art in Public Places Gallery in City Hall, 300 W. Plant Street
Art Exhibition: “Fun and/or Functional”
Thursday, December 9
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street
Garden Theatre Play: Big, The Musical
Thursday, December 9
2:00 pm
Garden Theatre, 160 West Plant Street
Garden Theatre Play: Big, The Musical
Thursday, December 9
7:30 pm
Garden Theatre, 160 West Plant Street
Art Exhibition: There’s a Map for That! Find Your Way Home: A Cartographic Survey of West Orange County
Friday, December 10
7:30 am - 5:30 pm
Curated by the Winter Garden Heritage Foundation
Art in Public Places Gallery in City Hall, 300 W. Plant Street
Art Exhibition: “Fun and/or Functional”
Friday, December 10
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street
Horse Drawn Holiday Carriage Tours
Friday, December 10
5:30 pm - 9:30 pm
Downtown Pavilion, 104 S. Lakeview Avenue
A Merry Winter Garden Light Show
Friday, December 10
6:00 pm - 9:00 pm
City Hall, 300 W. Plant St.
Holiday Live Music at Fridays on the Plaza
Friday, December 10
7:00 pm - 9:00 pm
Roots & Rosin
Downtown Winter Garden, Centennial Plaza
Garden Theatre Play: Big, The Musical
Friday, December 10
7:30 pm
Garden Theatre, 160 West Plant Street
Pilars – Visiting Artist Series
Friday, December 10
8:00 pm - 11:00 pm
USF's Jack Wilkins with John O'Leary, Paul Gavin & Noel Reves
146 W Plant St
Art Exhibition: “Fun and/or Functional”
Saturday, December 11
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street
Garden Theatre Play: Big, The Musical
Saturday, December 11
2:00 pm
Sensory Friendly Performance
Garden Theatre, 160 West Plant Street
Horse Drawn Holiday Carriage Tours
Saturday, December 11
5:30 pm - 9:30 pm
Downtown Pavilion, 104 S. Lakeview Avenue
A Merry Winter Garden Light Show
Saturday, December 11
6:00 pm - 9:00 pm
City Hall, 300 W. Plant St.
Garden Theatre Play: Big, The Musical
Saturday, December 11
7:30 pm
Garden Theatre, 160 West Plant Street
Pilars – Visiting Artist Series
Saturday, December 11
8:00 pm - 11:00 pm
Michelle Amato & Ed Krout
146 W Plant St
Garden Theatre Play: Big, The Musical
Sunday, December 12
2:00 pm
Garden Theatre, 160 West Plant Street
A Merry Winter Garden Light Show
Sunday, December 12
6:00 pm - 9:00 pm
City Hall, 300 W. Plant St.
Winter Garden Community Choir & Voci del Cuore: Noel! A Christmas Concert at the Garden Theatre
Sunday, December 12
7:30 pm
Click to reserve free ticket/$5 donation recommended.
Garden Theatre, 160 West Plant Street
Art Exhibition: There’s a Map for That! Find Your Way Home: A Cartographic Survey of West Orange County
Monday, December 13
7:30 am - 5:30 pm
Curated by the Winter Garden Heritage Foundation
Art in Public Places Gallery in City Hall, 300 W. Plant Street
Art Exhibition: There’s a Map for That! Find Your Way Home: A Cartographic Survey of West Orange County
Tuesday, December 14
7:30 am - 5:30 pm
Curated by the Winter Garden Heritage Foundation
Art in Public Places Gallery in City Hall, 300 W. Plant Street
Art Exhibition: “Fun and/or Functional”
Tuesday, December 14
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street
SOBO Art Gallery: Technique Tuesdays at 2pm
Tuesday, December 14
2:00 pm
"Oil" Nicora Gangi
Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street
Art Exhibition: There’s a Map for That! Find Your Way Home: A Cartographic Survey of West Orange County
Wednesday, December 15
7:30 am - 5:30 pm
Curated by the Winter Garden Heritage Foundation
Art in Public Places Gallery in City Hall, 300 W. Plant Street
Art Exhibition: “Fun and/or Functional”
Wednesday, December 15
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street
Art Exhibition: There’s a Map for That! Find Your Way Home: A Cartographic Survey of West Orange County
Thursday, December 16
7:30 am - 5:30 pm
Curated by the Winter Garden Heritage Foundation
Art in Public Places Gallery in City Hall, 300 W. Plant Street
Art Exhibition: “Fun and/or Functional”
Thursday, December 16
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street
Garden Theatre Play: Big, The Musical
Thursday, December 16
7:30 pm
Garden Theatre, 160 West Plant Street
Art Exhibition: There’s a Map for That! Find Your Way Home: A Cartographic Survey of West Orange County
Friday, December 17
7:30 am - 5:30 pm
Curated by the Winter Garden Heritage Foundation
Art in Public Places Gallery in City Hall, 300 W. Plant Street
Art Exhibition: “Fun and/or Functional”
Friday, December 17
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street
Horse Drawn Holiday Carriage Tours
Friday, December 17
5:30 pm - 9:30 pm
Downtown Pavilion, 104 S. Lakeview Avenue
A Merry Winter Garden Light Show
Friday, December 17
6:00 pm - 9:00 pm
City Hall, 300 W. Plant St.
Holiday Live Music at Fridays on the Plaza
Friday, December 17
7:00 pm - 9:00 pm
The Caroling Company - Safia Valines
Downtown Winter Garden, Centennial Plaza
Garden Theatre Play: Big, The Musical
Friday, December 17
7:30 pm
Garden Theatre, 160 West Plant Street
Pilars – Visiting Artist Series
Friday, December 17
8:00 pm - 11:00 pm
NYC's Adrian Cunningham with Per Danielsson, Charlie Silva & Walt Hubbard
146 W Plant St
Art Exhibition: “Fun and/or Functional”
Saturday, December 18
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street
Garden Theatre Play: Big, The Musical
Saturday, December 18
2:00 pm
Garden Theatre, 160 West Plant Street
Horse Drawn Holiday Carriage Tours
Saturday, December 18
5:30 pm - 9:30 pm
Downtown Pavilion, 104 S. Lakeview Avenue
A Merry Winter Garden Light Show
Saturday, December 18
6:00 pm - 9:00 pm
City Hall, 300 W. Plant St.
Garden Theatre Play: Big, The Musical
Saturday, December 18
7:30 pm
Garden Theatre, 160 West Plant Street
Pilars – Visiting Artist Series
Saturday, December 18
8:00 pm - 11:00 pm
Susy Park, Dave McKenzie & Chuck Archard
146 W Plant St
Garden Theatre Play: Big, The Musical
Sunday, December 19
2:00 pm
Garden Theatre, 160 West Plant Street
Horse Drawn Holiday Carriage Tours
Sunday, December 19
5:30 pm - 9:30 pm
Downtown Pavilion, 104 S. Lakeview Avenue
Christmas Golf Cart Parade
Sunday, December 19
5:45 pm
The tour will BEGIN and END at Bradford Park
Downtown Winter Garden
A Merry Winter Garden Light Show
Sunday, December 19
6:00 pm - 9:00 pm
City Hall, 300 W. Plant St.
Art Exhibition: There’s a Map for That! Find Your Way Home: A Cartographic Survey of West Orange County
Monday, December 20
7:30 am - 5:30 pm
Curated by the Winter Garden Heritage Foundation
Art in Public Places Gallery in City Hall, 300 W. Plant Street
Art Exhibition: There’s a Map for That! Find Your Way Home: A Cartographic Survey of West Orange County
Tuesday, December 21
7:30 am - 5:30 pm
Curated by the Winter Garden Heritage Foundation
Art in Public Places Gallery in City Hall, 300 W. Plant Street
Art Exhibition: “Fun and/or Functional”
Tuesday, December 21
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street
SOBO Art Gallery: Technique Tuesdays at 2pm
Tuesday, December 21
2:00 pm
"Colored Pencil" Meg Lung
Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street
Art Exhibition: There’s a Map for That! Find Your Way Home: A Cartographic Survey of West Orange County
Wednesday, December 22
7:30 am - 5:30 pm
Curated by the Winter Garden Heritage Foundation
Art in Public Places Gallery in City Hall, 300 W. Plant Street
Art Exhibition: “Fun and/or Functional”
Wednesday, December 22
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street
CDPA Performing Ensemble Dance: In His Name…We Dance
Wednesday, December 22
4:00 pm
Garden Theatre, 160 West Plant Street
Horse Drawn Holiday Carriage Tours
Wednesday, December 22
5:30 pm - 9:30 pm
Downtown Pavilion, 104 S. Lakeview Avenue
CDPA Performing Ensemble Dance: In His Name…We Dance
Wednesday, December 22
7:00 pm
Garden Theatre, 160 West Plant Street
Art Exhibition: There’s a Map for That! Find Your Way Home: A Cartographic Survey of West Orange County
Thursday, December 23
7:30 am - 5:30 pm
Curated by the Winter Garden Heritage Foundation
Art in Public Places Gallery in City Hall, 300 W. Plant Street
Art Exhibition: “Fun and/or Functional”
Thursday, December 23
10:00 am - 2:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street
CDPA Performing Ensemble Dance: In His Name…We Dance
Thursday, December 23
4:00 pm
Garden Theatre, 160 West Plant Street
Horse Drawn Holiday Carriage Tours
Thursday, December 23
5:30 pm - 9:30 pm
Downtown Pavilion, 104 S. Lakeview Avenue
A Merry Winter Garden Light Show
Thursday, December 23
6:00 pm - 9:00 pm
City Hall, 300 W. Plant St.
CDPA Performing Ensemble Dance: In His Name…We Dance
Thursday, December 23
7:00 pm
Garden Theatre, 160 West Plant Street
Horse Drawn Holiday Carriage Tours
Friday, December 24
5:30 pm - 9:30 pm
Downtown Pavilion, 104 S. Lakeview Avenue
Horse Drawn Holiday Carriage Tours
Sunday, December 26
5:30 pm - 9:30 pm
Downtown Pavilion, 104 S. Lakeview Avenue
Art Exhibition: There’s a Map for That! Find Your Way Home: A Cartographic Survey of West Orange County
Monday, December 27
7:30 am - 5:30 pm
Curated by the Winter Garden Heritage Foundation
Art in Public Places Gallery in City Hall, 300 W. Plant Street
Horse Drawn Holiday Carriage Tours
Monday, December 27
5:30 pm - 9:30 pm
Downtown Pavilion, 104 S. Lakeview Avenue
Art Exhibition: There’s a Map for That! Find Your Way Home: A Cartographic Survey of West Orange County
Tuesday, December 28
7:30 am - 5:30 pm
Curated by the Winter Garden Heritage Foundation
Art in Public Places Gallery in City Hall, 300 W. Plant Street
Art Exhibition: “Fun and/or Functional”
Tuesday, December 28
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street
SOBO Art Gallery: Technique Tuesdays at 2pm
Tuesday, December 28
2:00 pm
"Pastel" Nicora Gangi
Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street
Horse Drawn Holiday Carriage Tours
Tuesday, December 28
5:30 pm - 9:30 pm
Downtown Pavilion, 104 S. Lakeview Avenue
Art Exhibition: There’s a Map for That! Find Your Way Home: A Cartographic Survey of West Orange County
Wednesday, December 29
7:30 am - 5:30 pm
Curated by the Winter Garden Heritage Foundation
Art in Public Places Gallery in City Hall, 300 W. Plant Street
Art Exhibition: “Fun and/or Functional”
Wednesday, December 29
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street
Horse Drawn Holiday Carriage Tours
Wednesday, December 29
5:30 pm - 9:30 pm
Downtown Pavilion, 104 S. Lakeview Avenue
Art Exhibition: There’s a Map for That! Find Your Way Home: A Cartographic Survey of West Orange County
Thursday, December 30
7:30 am - 5:30 pm
Curated by the Winter Garden Heritage Foundation
Art in Public Places Gallery in City Hall, 300 W. Plant Street
Art Exhibition: “Fun and/or Functional”
Thursday, December 30
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street
Horse Drawn Holiday Carriage Tours
Thursday, December 30
5:30 pm - 9:30 pm
Downtown Pavilion, 104 S. Lakeview Avenue
January 2022
Art Exhibition: There’s a Map for That! Find Your Way Home: A Cartographic Survey of West Orange County
Monday, January 3
7:30 am - 5:30 pm
Curated by the Winter Garden Heritage Foundation
Art in Public Places Gallery in City Hall, 300 W. Plant Street
Art Exhibition: There’s a Map for That! Find Your Way Home: A Cartographic Survey of West Orange County
Tuesday, January 4
7:30 am - 5:30 pm
Curated by the Winter Garden Heritage Foundation
Art in Public Places Gallery in City Hall, 300 W. Plant Street
Art Exhibition: “Fun and/or Functional”
Tuesday, January 4
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street
SOBO Art Gallery: Technique Tuesdays at 2pm
Tuesday, January 4
2:00 pm
"Colored Pencil" Meg Lung
Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street
Art Exhibition: There’s a Map for That! Find Your Way Home: A Cartographic Survey of West Orange County
Wednesday, January 5
7:30 am - 5:30 pm
Curated by the Winter Garden Heritage Foundation
Art in Public Places Gallery in City Hall, 300 W. Plant Street
Art Exhibition: “Fun and/or Functional”
Wednesday, January 5
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street
Art Exhibition: There’s a Map for That! Find Your Way Home: A Cartographic Survey of West Orange County
Thursday, January 6
7:30 am - 5:30 pm
Curated by the Winter Garden Heritage Foundation
Art in Public Places Gallery in City Hall, 300 W. Plant Street
Art Exhibition: “Fun and/or Functional”
Thursday, January 6
10:00 am - 6:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street
Art Exhibition: There’s a Map for That! Find Your Way Home: A Cartographic Survey of West Orange County
Friday, January 7
7:30 am - 5:30 pm
Curated by the Winter Garden Heritage Foundation
Art in Public Places Gallery in City Hall, 300 W. Plant Street