While enjoying the special sales during the Sidewalk Sale, take in these cultural and recreational entertainment bargains that are located amongst the shops and are always free! Click here to download to a full map and list of the Merchants and Entertainment that will be featured.

  1. SOBO Art Gallery (Winter Garden Art Association)

    127 S. Boyd Street
    Tuesday - Saturday: 10:00 am – 6:00pm.
    Closed Sunday, Monday, and Major Holidays
    Free Children’s Art Project during the Sidewalk Sale on Sat., Sept. 28th, 11:00 am – 5:00 pm. Children invited to produce their own fall masterpiece to take home under the guidance of Lenore Eastham, a certified art educator. There is no cost, so come, relax and let your children experience the joy of art. (Parents must accompany their children)
  2. Winter Garden Heritage Museum

    One N. Main Street
    Open Every Day: 1:00 pm – 5:00 pm
    Take a free tour at one the heritage museums while you are at the Sidewalk Sale.
  3. History Research & Education Center and Visitors’ Center

    21 E. Plant Street
    Monday – Friday: 11:00 am – 5:00 pm
    Saturday: 9:00 am – 5:00 pm
    Sunday: 11:00 am – 5:00 pm
  4. Central Florida Railroad Museum

    101 S. Boyd Street
    Open Every Day: 1:00 pm – 5:00 pm
  5. Downtown Interactive Fountain/Splash Pad

    230 W. Plant Street
    When your children in tow need a break from shopping, they can splash and cool off right in the heart of downtown, with plenty of ample seating for parents to watch and enjoy!
  6. Centennial Plaza - Winter Garden’s Outdoor Living Room

    101 W. Plant Street
    Rest your shopping legs by grabbing a seat on the bench swings that surround the picturesque mosaic-tiled, renaissance fountain. Besides, these are prime seats for the live musical acts during the Sidewalk Sale!
  7. Winter Garden Farmers Market

    104 S. Lakeview Avenue
    Saturday, Sept. 29th, 9:00 am – 2:00 pm
    If you come to the Sidewalk Sale on Saturday, be sure to experience the national award-winning Farmers Market which boasts great prices on fresh, local produce and unique items.
  8. Woodstone Jewelry

    31 S. Main Street / 426 W. Plant St./ 27 N Dillard St.
    Make & Take Classes – Reveal your creative side and have some fun as you select what you want, make it on the spot, and take your personally hand-made jewelry with you. These individual classes will run continuously during the Sidewalk Sale (11:00 am-5:00 pm, Sept. 27-29). Most jewelry can be made in 10 minutes! Cost: $5.00-$10.00.
  9. Winter Garden Wheel Works

    101 W. Plant St.
    Free Bike Raffle at Winter Garden Wheel Works, 101 W. Plant St. To enter to win, stop in Winter Garden Wheel Works starting Thurs, Sept. 27, through 5 pm on Sat., Sept. 29. The drawing for the FREE BIKE will be held at the Centennial Plaza Gazebo at 5 pm on Sat., Sept. 29. 
  10. Nancy's Quilt Shop

    121 W. Plant St.
    Free Portable Sewing Machine Raffle at Nancy’s Quilt Shop, 121 W. Plant St. To enter to win, stop in Nancy’s Quilt Shop starting Thurs, Sept. 27, through 5 pm on Sat., Sept. 29.

Live Music Performances

Please see music schedule for line-up up free live musical performances throughout the Shop Local September Sidewalk Sale!

Thursday, September 27
2pm - 5pm Nicole Equerme
Friday, September 28
11am - 2pm Spayed Koolie
3pm - 6pm Jonnie Morgan
7pm - 9pm Good Times Jazz Band
Saturday, September 29
10am - 1pm Abby Baird (at the Farmers Market)
11pm - 2pm Sean Holcomb
3pm - 6pm Mud Rooster