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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; quarterly Cruz ‘N Car Show; to the annual Spring Fever in the Garden, Halloweenfest, Shop Small Business Saturday, and month-long ‘Tis the Season events — there is always something happening Downtown!
April 2020
No events scheduled at this time.
May 2020
June 2020
Winter Garden Farmers Market
Saturday, June 6
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Winter Garden Farmers Market
Saturday, June 13
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Winter Garden Farmers Market
Saturday, June 20
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
July 2020
Winter Garden Farmers Market
Saturday, July 4
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Winter Garden Farmers Market
Saturday, July 11
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Winter Garden Farmers Market
Saturday, July 18
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
August 2020
Winter Garden Farmers Market
Saturday, August 1
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Winter Garden Farmers Market
Saturday, August 8
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Winter Garden Farmers Market
Saturday, August 15
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Fridays on the Plaza
Friday, August 21
7:00 pm - 9:00 pm
Music: Jason Thomas (Folk, Bluegrass)
Downtown Winter Garden
Winter Garden Farmers Market
Saturday, August 22
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Fridays on the Plaza
Friday, August 28
7:00 pm - 9:00 pm
Music: Good Times Jazz Band (Jazz)
Downtown Winter Garden
September 2020
Winter Garden Farmers Market
Wednesday, September 2
3:00 pm - 7:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Fridays on the Plaza
Friday, September 4
7:00 pm - 9:00 pm
Music: Jade Frances (Pop, Acoustic)
Downtown Winter Garden
Winter Garden Farmers Market
Saturday, September 5
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Winter Garden Farmers Market
Wednesday, September 9
3:00 pm - 7:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Fridays on the Plaza
Friday, September 11
7:00 pm - 9:00 pm
Music: Da Capo Jazz Trio (Jazz)
Downtown Winter Garden
Winter Garden Farmers Market
Saturday, September 12
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Winter Garden Farmers Market
Wednesday, September 16
3:00 pm - 7:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Fridays on the Plaza
Friday, September 18
7:00 pm - 9:00 pm
Music: Keith Eaton (Soul)
Downtown Winter Garden
Winter Garden Farmers Market
Saturday, September 19
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Winter Garden Farmers Market
Wednesday, September 23
3:00 pm - 7:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Fridays on the Plaza
Friday, September 25
7:00 pm - 9:00 pm
Cancelled Until Further Notice
Downtown Winter Garden
Winter Garden Farmers Market
Saturday, September 26
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
October 2020
Winter Garden Farmers Market
Saturday, October 3
8:00 pm - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Winter Garden Farmers Market
Wednesday, October 7
3:00 pm - 7:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Winter Garden Farmers Market
Saturday, October 10
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Winter Garden Farmers Market
Wednesday, October 14
3:00 pm - 7:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Winter Garden Farmers Market
Saturday, October 17
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Winter Garden Farmers Market
Wednesday, October 21
3:00 pm - 7:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Winter Garden Farmers Market
Saturday, October 24
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Winter Garden Farmers Market
Wednesday, October 28
3:00 am - 7:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
November 2020
Winter Garden Farmers Market
Saturday, November 7
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Winter Garden Farmers Market
Saturday, November 14
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Winter Garden Farmers Market
Saturday, November 21
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Shop Small Business Saturday
Saturday, November 28
8:00 am - 10:00 pm
Downtown Winter Garden Sidewalk Sale
December 2020
Holiday Horse Drawn Carriage Tours
Friday, December 4
5:30 pm - 9:30 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
A Merry Winter Garden Light Show
Friday, December 4
6:00 pm - 9:00 pm
City Hall, 300 W. Plant St.
Winter Garden Farmers Market
Saturday, December 5
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Holiday Horse Drawn Carriage Tours
Saturday, December 5
5:30 pm - 9:30 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
A Merry Winter Garden Light Show
Saturday, December 5
6:00 pm - 9:00 pm
City Hall, 300 W. Plant St.
Holiday Boutique Stroll & Sale
Thursday, December 10
8:00 am - 8:00 pm
Downtown Winter Garden
Dickens Carolers
Thursday, December 10
5:00 pm - 7:00 pm
Downtown Winter Garden
Holiday Horse Drawn Carriage Tours
Friday, December 11
5:30 pm - 9:30 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
A Merry Winter Garden Light Show
Friday, December 11
6:00 pm - 9:00 pm
City Hall, 300 W. Plant St.
Winter Garden Farmers Market
Saturday, December 12
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Holiday Horse Drawn Carriage Tours
Saturday, December 12
5:30 pm - 9:30 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
A Merry Winter Garden Light Show
Saturday, December 12
6:00 pm - 9:00 pm
City Hall, 300 W. Plant St.
A Merry Winter Garden Light Show
Sunday, December 13
6:00 pm - 9:00 pm
City Hall, 300 W. Plant St.
Holiday Horse Drawn Carriage Tours
Friday, December 18
5:30 pm - 9:30 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
A Merry Winter Garden Light Show
Friday, December 18
6:00 pm - 9:00 pm
City Hall, 300 W. Plant St.
Winter Garden Farmers Market
Saturday, December 19
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Holiday Horse Drawn Carriage Tours
Saturday, December 19
5:30 pm - 9:30 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
A Merry Winter Garden Light Show
Saturday, December 19
6:00 pm - 9:00 pm
City Hall, 300 W. Plant St.
Dickens Carolers
Saturday, December 19
6:30 pm - 8:30 pm
Downtown Winter Garden
Winter Garden Farmers Market
Saturday, December 26
8:00 am - 1:00 pm
Market Cancelled due to the Holidays
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Holiday Horse Drawn Carriage Tours
Saturday, December 26
5:30 pm - 9:30 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Holiday Horse Drawn Carriage Tours
Sunday, December 27
5:30 pm - 9:30 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Holiday Horse Drawn Carriage Tours
Monday, December 28
5:30 pm - 9:30 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Holiday Horse Drawn Carriage Tours
Tuesday, December 29
5:30 pm - 9:30 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
January 2021
Winter Garden Farmers Market
Saturday, January 2
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Winter Garden Farmers Market
Saturday, January 9
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Winter Garden Farmers Market
Saturday, January 16
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Celebrate MLK Day and Black History Month in Winter Garden
Monday, January 18
8:00 am - 9:00 pm
Downtown Winter Garden
Winter Garden Farmers Market
Saturday, January 23
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
February 2021
Winter Garden Farmers Market
Saturday, February 6
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Horse Drawn Carriage Tours for your Valentine
Friday, February 12
6:00 pm - 10:00 pm
Downtown Pavilion – 104 S. Lakeview Avenue
Winter Garden Farmers Market
Saturday, February 13
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Horse Drawn Carriage Tours for your Valentine
Saturday, February 13
6:00 pm - 10:00 pm
Downtown Pavilion – 104 S. Lakeview Avenue
Horse Drawn Carriage Tours for your Valentine
Sunday, February 14
6:00 pm - 10:00 pm
Downtown Pavilion – 104 S. Lakeview Avenue
Live Music @ Crooked Can
Friday, February 19
6:00 pm - 9:00 pm
Crooked Can 426 W. Plant Street
Winter Garden Farmers Market
Saturday, February 20
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Live Music @ Crooked Can
Saturday, February 20
1:00 pm
Crooked Can 426 W. Plant Street
Live Music @ Crooked Can
Sunday, February 21
1:00 pm - 4:00 pm
Crooked Can 426 W. Plant Street
Live Music @ Crooked Can
Friday, February 26
6:00 pm - 9:00 pm
Crooked Can 426 W. Plant Street
Winter Garden Farmers Market
Saturday, February 27
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Live Music @ Crooked Can
Saturday, February 27
1:00 pm
Crooked Can 426 W. Plant Street
Live Music @ Crooked Can
Sunday, February 28
1:00 pm - 4:00 pm
Crooked Can 426 W. Plant Street
March 2021
Garden Theatre Play: A Raisin in the Sun
Wednesday, March 3
7:30 pm
Garden Theatre 160 West Plant Street
Winter Garden Farmers Market
Saturday, March 6
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Live Music @ Crooked Can
Friday, March 12
6:00 pm - 9:00 pm
Dan Harshbarger & Tony Mickle- Beemo
Crooked Can 426 W. Plant Street
Winter Garden Farmers Market
Saturday, March 13
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Live Music @ Crooked Can
Saturday, March 13
12:00 pm - 3:00 pm
Scotty Long
Crooked Can 426 W. Plant Street
Live Music @ Crooked Can
Saturday, March 13
6:00 pm - 9:00 pm
Lisa McIntyre & Sharon Hartmann
Crooked Can 426 W. Plant Street
Live Music @ Crooked Can
Sunday, March 14
1:00 pm - 4:00 pm
Ennis Pruitt
Crooked Can 426 W. Plant Street
Live Music @ Crooked Can
Friday, March 19
6:00 pm - 9:00 pm
Dan Harshbarger & Tony Mickle- Beemo
Crooked Can 426 W. Plant Street
Winter Garden Farmers Market
Saturday, March 20
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Live Music @ Crooked Can
Saturday, March 20
1:00 pm - 4:00 pm
Ennis Pruitt
Crooked Can 426 W. Plant Street
Live Music @ Crooked Can
Saturday, March 20
6:00 pm - 9:00 pm
Scotty Long
Crooked Can 426 W. Plant Street
Live Music @ Crooked Can
Sunday, March 21
1:00 pm - 4:00 pm
Dan Harshbarger & Tony Mickle- Beemo
Crooked Can 426 W. Plant Street
Virtual Event- Conversation with award-winning author Adam Levin & Nathan Englander
Tuesday, March 23
7:00 pm
Free event
Writer's Block Bookstore- Virtual Event
Virtual Event- Book Launch with Heather Graham
Tuesday, March 23
7:00 pm
Tickets $32
Writer's Block Bookstore- Virtual Event
When Winter Garden Was Oakland
Thursday, March 25
6:30 pm
Author Richard Cronin will tell the story of the settlement and founding of the Oakland - Winter Garden region
Winter Garden Heritage Foundation Facebook Live Event
Winter Garden Farmers Market
Saturday, March 27
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
April 2021
Art Exhibition “The World Outside” Opening Reception
Thursday, April 1
5:30 pm - 8:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio 127 S. Boyd Street
Pilars- Thursday’s Singers Open Mic
Thursday, April 1
7:00 pm - 10:00 pm
Weekly Billy Flanigan, Host & Kelly DeWayne Richards on Piano
146 W Plant St STE 120
Music in Pilars Loft
Friday, April 2
CD Release- Thoughts on the Matter. Ryan Devlin (Sax), Per Danielsson (Piano), Ulysses Owens Jr. (D) & Thomas Milovac (B)
146 W Plant St.
Music in Pilars Loft
Saturday, April 3
Scott Dickinson & Bobby Koelble
146 W Plant St.
Winter Garden Farmers Market
Saturday, April 3
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Pilars- Thursday’s Singers Open Mic
Thursday, April 8
7:00 pm - 10:00 pm
Weekly Billy Flanigan, Host & Kelly DeWayne Richards on Piano
146 W Plant St STE 120
Music in Pilars Loft
Friday, April 9
Tamara & Per Danielsson
146 W Plant St.
Music in Pilars Loft
Saturday, April 10
Joe Breidenstine Trio
146 W Plant St.
Winter Garden Farmers Market
Saturday, April 10
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Virtual Event- Conversation with author Marina Khidekel and Arianna Huffington
Tuesday, April 13
6:30 pm
Tickets $28 - $31
Writer's Block Bookstore- Virtual Event
Pilars- Thursday’s Singers Open Mic
Thursday, April 15
7:00 pm - 10:00 pm
Weekly Billy Flanigan, Host & Kelly DeWayne Richards on Piano
146 W Plant St STE 120
Music in Pilars Loft
Friday, April 16
Michelle Amato & Ed Krout
146 W Plant St.
Music in Pilars Loft
Saturday, April 17
Pilars Loft Showcase- Pilars Trio Per Danielson, Charlie Silva & Walt Hubbard
146 W Plant St.
Winter Garden Farmers Market
Saturday, April 17
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Pilars- Thursday’s Singers Open Mic
Thursday, April 22
7:00 pm - 10:00 pm
Weekly Billy Flanigan, Host & Kelly DeWayne Richards on Piano
146 W Plant St STE 120
Garden Theater Play: Godspell
Thursday, April 22
7:30 pm
Garden Theater 160 West Plant Street
Music in Pilars Loft
Friday, April 23
Suzy Park & Ed Krout
146 W Plant St.
Garden Theater Play: Godspell
Friday, April 23
7:30 pm
Garden Theater 160 West Plant Street
Music in Pilars Loft
Saturday, April 24
Ella & the Bossa Beat
146 W Plant St.
Winter Garden Farmers Market
Saturday, April 24
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Independent Bookstore Day
Saturday, April 24
10:00 am - 8:00 pm
Free event with coupon scavenger hunt, prize wheel, and more!
Writer's Block Bookstore 32 W Plant St, Winter Garden, FL 34787
Garden Theater Play: Godspell
Saturday, April 24
2:00 pm
Garden Theater 160 West Plant Street
Garden Theater Play: Godspell
Saturday, April 24
7:30 pm
Garden Theater 160 West Plant Street
Garden Theater Play: Godspell
Sunday, April 25
2:00 pm
Garden Theater 160 West Plant Street
Pilars- Thursday’s Singers Open Mic
Thursday, April 29
7:00 pm - 10:00 pm
Weekly Billy Flanigan, Host & Kelly DeWayne Richards on Piano
146 W Plant St STE 120
Garden Theater Play: Godspell
Thursday, April 29
7:30 pm
Garden Theater 160 West Plant Street
Garden Theater Play: Godspell
Friday, April 30
7:30 pm
Garden Theater 160 West Plant Street
Music in Pilars Loft
Friday, April 30
8:00 pm - 11:00 pm
Tamara & Per Danielsson
146 W Plant St.
May 2021
Winter Garden Farmers Market
Saturday, May 1
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Garden Theater Play: Godspell
Saturday, May 1
2:00 pm
Garden Theater 160 West Plant Street
Garden Theater Play: Godspell
Saturday, May 1
7:30 pm
Garden Theater 160 West Plant Street
Garden Theater Play: Godspell
Sunday, May 2
2:00 pm
Garden Theater 160 West Plant Street
Garden Theater Play: Godspell
Thursday, May 6
2:00 pm
Garden Theater 160 West Plant Street
Pilars- Thursday’s Singers Open Mic
Thursday, May 6
7:00 pm - 10:00 pm
Weekly Billy Flanigan, Host & Kelly DeWayne Richards on Piano
146 W Plant St STE 120
Garden Theater Play: Godspell
Thursday, May 6
7:30 pm
Garden Theater 160 West Plant Street
Garden Theater Play: Godspell
Friday, May 7
7:30 pm
Garden Theater 160 West Plant Street
Winter Garden Farmers Market
Saturday, May 8
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Garden Theater Play: Godspell
Saturday, May 8
2:00 pm
Garden Theater 160 West Plant Street
Garden Theater Play: Godspell
Saturday, May 8
7:30 pm
Garden Theater 160 West Plant Street
Garden Theater Play: Godspell
Sunday, May 9
2:00 pm
Garden Theater 160 West Plant Street
Garden Theater Play: Godspell
Thursday, May 13
2:00 pm
Garden Theater 160 West Plant Street
Pilars- Thursday’s Singers Open Mic
Thursday, May 13
7:00 pm - 10:00 pm
Weekly Billy Flanigan, Host & Kelly DeWayne Richards on Piano
146 W Plant St STE 120
Garden Theater Play: Godspell
Thursday, May 13
7:30 pm
Garden Theater 160 West Plant Street
Garden Theater Play: Godspell
Friday, May 14
7:30 pm
Garden Theater 160 West Plant Street
Winter Garden Farmers Market
Saturday, May 15
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
Garden Theater Play: Godspell
Saturday, May 15
2:00 pm
Garden Theater 160 West Plant Street
Garden Theater Play: Godspell
Saturday, May 15
7:30 pm
Garden Theater 160 West Plant Street