Harvest Sidewalk Sale & Stroll

Harvest Sidewalk Sale 2022


Saturday, October 22 Daylong

Historic Downtown Winter Garden

Stroll and shop the outdoor sidewalk sale surrounded by the City of Winter Garden Halloween Experience festivities and decorations. Stores will feature outdoor and indoor special sales, promotions, and seasonal merchandise. Dine at the outdoor patios to enjoy the fall weather amidst the spooky- and fall-themed décor.

The unique shops of downtown feature apparel, jewelry, home décor and greenery, cycling/running /sporting equipment and accessories, gourmet foods, health and beauty products, pet supplies, furniture, and much more. For a list of downtown shops, click here and click here for a list of Dining options. 

The diverse selection of eateries, bakeries, and coffee shops are ideal for a shopping break and enjoying the fall ambiance. Enjoy seasonal menu items at many of the locations; and of course, the fall fan favorite: pumpkin spice latte

At the Sidewalk Sale, you will find fun things to do for the whole family including a Hay Maze at City Hall, themed photo stations, Halloween- and fall-themed decorations and light displays, as well as evening events such as a Halloween Light Show, live music, and surprise strolling entertainment. All activities and events are FREE.

Be sure to also stop by the Winter Garden Library Sidewalk Sale, 10:00 am - 2:00 pm, to find discounted books, DVDs, Blu-rays, CDs, and more. 805 E. Plant St.


COME EARLY for the ripe fall harvest at the Winter Garden Farmers Market (8:00 am-1:00 pm).

STAY LATE to enjoy the Halloween Experience festivities including fun, complimentary entertainment: 

  • Live Music, Shows, and Pop-up Street Performers, 6-9 pm
  • Halloween Light Show on City Hall, 7-9 pm

For more information about the annual Halloween Experience (October 21-31), click here


Convenient parking is always free throughout Downtown Winter Garden, including at the City’s three-level parking garage (160 S. Boyd St.) and the new 117-space parking lot (37 N. Boyd St.).

Harvest Sidewalk Sale Stroll Flyer