Arts in April 2023

Arts in April 2022


In celebration of World Art Day, the Winter Garden Art Association and community partners will host a series of events throughout the month of April to raise awareness for local art organizations and artists, while providing opportunities for the community to explore and create art. All of the events are FREE, except for the fundraiser Art Night VIP.


Kids will enjoy the free art activities hosted by the Winter Garden Art Association under the Art Tent at the Winter Garden Farmers Market.

Saturday │ April 8, 15, & 22

9:00 am – 12:00 pm │ Free

Winter Garden Farmers Market/Parking Garage Plaza, 160 S. Boyd Street


Artists’ works will be illuminated on the front façade of City Hall, creating a visually stunning immersive art experience. The public is invited to stroll by, grab a nearby bench, or bring a chair to enjoy the beautiful display powered by projection mapping.

Saturday, April 30 Time TBA

City Hall, 300 W. Plant Street 


The Bloom & Grow Garden Society presents the annual Chalkin’ It Up Sidewalk Art Contest at Spring Fever in the Garden. Contestants of all ages bring the area in front of City Hall to life with nature-related art. The contestants start at daybreak and judging takes place at 4:00 pm. Stroll by and see their creativity in action. The amazing creations will remain for viewing throughout the weekend, weather permitting.

The contest is free to enter and prizes will be awarded. Contestants must bring their own chalk and supplies. Space is limited and registration deadline is March 17,

Saturday, April 1 │ Contest, 6:00 am - 4:00 pm (Judging) / Viewing, All Day

Sunday, April 2 │ Viewing, All Day

City Hall, 300 W. Plant Street


SOBO’s Annual Awards Exhibition showcases the best 2D & 3D works of art. Awards are presented for Best of Show, People’s Choice, Curator’s Choice, and Multiple Medium Category Winners.


April 1 - May 27

Tuesday – Friday │11:00 am – 5:00 pm

Saturday │ 10:00 am – 4:00 pm

SOBO Art Gallery, 127 S. Boyd Street │ Free

Opening Reception 

April 6, 5:30 - 8:00 pm │ Public Invited

 SOBO Art Gallery, 127 S. Boyd Street │ Free

     Call to Artists

          Outside Call to Artists for Top Choice Annual Awards Show -- DEADLINE: March 1-8

          Artists are encouraged to submit their best 2D & 3D works, open to all types of artistic entries. Winning entries will be featured as            part of the Top Choice Annual Awards Show that will be on display April 1 - May 27 at SOBO Art Gallery. 

           Entries are accepted March 1 - 8, 2023.  Submit at

Exhibition: High School Top Choice Awards Show

A selection of 2D and 3D works of art from area high school students. 


April 1 – June 2 

Monday – Friday, 7:30 am – 5:30 pm (City Hall operating hours)

City Hall Art in Public Places Gallery, 300 W. Plant Street

Awards Reception

April 6, 5:00 – 6:00 pm Public Invited

City Hall Art in Public Places Gallery, 300 W. Plant Street


Join artists to paint en plein air at the Winter Garden Farmers Market or anywhere in historic downtown, -- or come witness their creations come to life.

Urban Sketchers: Check in starts at 9:00 am at SOBO Art Gallery. Bring blank paper or canvas to be stamped at check-in. Create art anywhere around Winter Garden Farmers Market or along Plant Street. Submit two photos of completed art (one showing Urban Sketchers stamp) online at by 6:00 pm. Winners announced on April 18.

Saturday, April 15 │ 9:00 am – 2:00 pm │ Check-in starts at 9:00 am 

SOBO Art Gallery, 127 S. Boyd Street │407.347.7996  Free 

Winter Garden Farmers Market, 104 S. Lakeview Avenue / Along West Plant Street


Art Night VIP -- Immersive Art Experience (annual fundraiser)

Immerse yourself in the arts on this special night that includes a variety of art experiences, a silent art auction, beverages, and light appetizers, Projection Art Show on City Hall, and surprise entertainment.

Individual tickets are $75. Ticket price includes a $35 annual membership to the Winter Garden Art Association, which provides perks throughout the year. Sponsorship packages, which include complimentary tickets, are also available. The event is a fundraiser to benefit the 501c3 non-profit Winter Garden Art Association. Purchase tickets in advance at

Saturday, April 29  6:30 – 10:00 pm

Historic Downtown

Ticketed Event,


A variety of auction items will be available at SOBO Art Gallery throughout April to preview and bid on. The Auction will also  be available during Art Night VIP in addition to a live silent auction. A great way to get unique items while supporting the Winter Garden Art Association.

SOBO Art Gallery, 127 S. Boyd Street, 407.347.7996,

LIVE MUSIC at Fridays on the Plaza

Music is one of the fine arts and April is a great time to enjoy local talent. Enjoy a free outdoor live music performance every Friday night in historic downtown, hosted by the City of Winter Garden.

Live Music Schedule

  • April 7- Sound Traveler Band (Acoustic, Pop)
  • April 14- Bird Dog Bobby (Blues)
  • April 21- Retro Ramblers (Oldies, Pop)
  • April 28- The Lynne Gibson Project (Folk, Bluegrass

7:00 - 9:00 pm

Centennial Plaza Gazebo, Historic Downtown

ART CLASES at SOBO Art Gallery & Studio

Technique Tuesday @ 2pm 

A different instructor each week shares knowledge and technique tips. This weekly "create" event is a great opportunity for all skill levels to learn, grow, and be inspired through the talents of other artists. Visit on Tuesdays throughout the month of April as well as all year long.

Tuesdays | 2:00 - 4:00 pm | Free for Members and First Time Visitors

Registration required at

SOBO Art Gallery, 127 S. Boyd Street, 407.347.7996

Artist Night Studio: Life Drawing

Model is available to draw every Wednesday night.

Wednesdays | 6:30 – 9:00 pm

18 years and older only

$10 member / $15 nonmember (collected at sign in)

SOBO Art Gallery, 127 S. Boyd Street, 407.347.7996,

Open Studio Saturdays

Bring your own supplies and enjoy creating in our studio room -- or on our outdoor front patio with the Farmers Market (open through 1:00 pm) just steps away. Must bring your own drop cloth (and shading if necessary) when painting outside. Reserve your space today at

Saturdays | 10:00 am – 5:00 pm | Members Only

SOBO Art Gallery, 127 S. Boyd Street, 407.347.7996.


World War II and West Orange County at Winter Garden Heritage Museum

Visit the Museum during the month of April to view the exhibit featuring photographs and artifacts honoring the service personnel who served in World War II both at home and abroad.

March 1 – May 31  | Free Admission

Winter Garden Heritage Museum

1 N. Main Street

Tuesday – Saturday | 11:00 am – 3:00 pm


Spring Open House at Central Florida Railroad Museum

Saturday, April 1 │ 9:00 am - 5:00 pm (extended museum hours) │ Special Presentation, 1:00 pm | Free

Pop inside the Central Florida Railroad Museum during the month of April to see the amazing artifacts and memorabilia. On April 1st, the Museum will host an Open House with extended hours and a special presentation at 1:00 pm. 

Central Florida Railroad Museum

101 S. Boyd Street

Tuesday – Saturday │11:00 am – 3:00 pm  │ Free Admission



Something Rotten  at the Garden Theatre

Brothers Nick and Nigel Bottom are writing their way through the Renaissance, but are stuck in the shadow of famed playwright William Shakespeare. Sick and tired of failure, Nick visits a less-than-reputable soothsayer, who predicts that musicals will be the next big thing in theatre! The Bottom Brothers scramble to write the world’s first musical while fighting social norms, family struggles, and “The Bard” himself. Will opening night be an over-easy success or a rotten mess? 

Starts April 21

Buy tickets

Garden Theatre, 160 W. Plant Street, 407.877.4736


Keep an eye out for other “pop-up” art and cultural activities and events in Winter Garden during the month of April.