Downtown Winter Garden Summer Sidewalk Sale

SPONSORED – Support local businesses and enjoy free live music while strolling the streets of Winter Garden’s picturesque downtown during the upcoming Summer Sidewalk Sale on Saturday, June 8, 2019.

From 11am-7pm, Downtown Winter Garden will be transformed into a lively market featuring special deals and raffles from dozens of unique local retailers, restaurants, bars and more. Browsing the shops, outdoor sales racks and tables, you’ll find deals on everything from dog treats to theatre tickets and even a scavenger hunt through downtown to win Winter Garden Food Tours tickets.

Continue your date day by popping over to the Winter Garden Farmer’s Market (9am-2pm) for more local goodies. SOBO Art Gallery will also host a free children’s art project from 11am-5pm.


Besides the lineup of 25+ local retailers, the Summer Sidewalk Sale will feature continuous live music at the Centennial Plaza Gazebo.

The live music lineup will feature:

  • Mud Rooster: 11am-2:30pm
  • SPAYED KOOLIE: 3:30-7pm


Adjectives Market | 137 W. Plant St.

  • Market-style sidewalk sale – patrons can negotiate prices for great deals
  • Sale racks outside of store with special-priced merchandise
  • Inside store sales and complimentary food sample
  • Raffle to win an Annie Sloan Chalk Paint Start-Up Kit Basket

The Boutique on Plant | 111 W. Plant St.

  • Specially priced sidewalk sale items
  • 15% discount with a purchase of $100 or more on regularly priced merchandise, excluding Brighton

Burger Fi | 360 W. Plant St.

  • FREE small custard with purchase of a burger and fries

Cambridge Home IDEAs | 27 N. Dillard St.

  • Various sales and discounts throughout the store
  • FREE 3 oz. Florida Salt Scrub with purchase

Divine Wellness | 33 S. Main St.

  • 20% discount on entire product lines of the following: Root Nutritionals CBD, Nature’s Sunshine Products, Barlean’s Organic Oils, Europharma, Filthy Farm Girl, Gemstones & Jewelry collections
  • FREE product or service giveaways with purchase

Doxology | 49 S. Main St.

  • Free Bracelet with $50 minimum purchase
  • In-store raffle
  • Select merchandise up to 50% off

Driftwood Market | 46 W Plant St.

  • Sale tables outside with special priced merchandise
  • Select merchandise up to 60% off inside store

4 Locos Tacos | 360 W. Plant St.

  • Free chips and salsa with purchase of a “4 Locos Tacos Special”

Garden Music School | 40 S. Main St.

  • 20% off all retail and lesson packages
  • 25% off Fender Guitars

Garden Theatre | 160 W. Plant St.

  • 24% off tickets to the Theatre season with a 3-Pack Subscription. Choose the three theatre shows you want to see and when you want to see them. Only $84. 

Kitlife | 100 S. Boyd St.

  • 20% off storewide

Melts on Main | 108 S. Main St.

  • Buy ONE Melt Sandwich, GET ONE 50% OFF
  • Buy ONE hand-crafted Sangria, GET ONE 50% OFF

Ms. Bee’s Gourmet Popcorn and Candy Shop | 2 E. Plant St.

  • 15% OFF any size of these popular popcorn flavors: Cheesy Cheddar, Spicy Buffalo, Cornfetti, Caramel & Cheddar, and Caramel Chocolate Drizzle (in-store special)

One Utopia | Pop-up location at 162 W. Plant St.

  • 20% discount on health and beauty items
  • A special-priced $10 section on fair trade clothing such as tank tops, harem pants, and more

Pilars Martini | 146 W. Plant St.

  • Mimosa & Champagne specials for shoppers showing a receipt from a downtown merchant dated June 8, 2019

winter garden
Image credit: Pilars Martini Bar

Sacred Olive | 125 W. Plant St.

  • 25% off Violet Balsamic
  • Sale on select floral collections of Balsamic & Olive Oil

Silver Shekel Shop | 146 W. Plant St.

  • 20% off specially-marked items including inspirational home décor and imported glassware
  • Outside display tables with specially-priced inspirational gifts and locally produced resources

SOBO Art Gallery / Winter Garden Art Association | 127 S. Boyd St.

  • Visit nearly a dozen artists under tents outside of the SOBO Art Gallery showcasing their artwork for sale
  • FREE Children’s Art Project from 11am-5pm: Children (must be accompanied by adult) invited to produce their own masterpiece to take home under the guidance of Lenore Eastham, a certified art educator

Tack Boutique | 21 S. Main St.

  • 20% off all home decor and jewelry items
  • Sale merchandise displayed outside

Tri & Run | 56 W. Plant St.

  • Sale table shoe closeouts 30-50% off
  • Select Spenco sandals $10 off

Victor Russell Etc. | 115 W. Plant St.

  • Special sale on select clothing, plants and “Christmas in June” sidewalk sale items!

Wildflower Beauty by Jessica | 100 W. Plant St.

  • Free gift with $50 purchase, while supplies last
  • Face care 15% off
  • Hair care 10% off
  • Sugar scrubs buy 1 get 1 50% off
  • Additional items on sale throughout the store, up to 30% off

Winter Garden Food Tours | Pop-up location at 162 W. Plant St.

  • Scavenger Hunt through the downtown area to win prizes. Prizes will include:
    • Passes for two to Summertime Classic Tour (featured in June and July) Value of $90.00
    • Passes for two to Date Night Cooking Classes (featured in June and July) Value of $130.00

Winter Garden Wheel Works | 101 W. Plant St.

  • 50% OFF selected items
  • Select bicycles 25% OFF
  • Gift cards — Get $50 for $40, $100 for $75
  • Each purchase will be entered into a drawing for a free $100 gift card

Woodstone Jewelry | 46 W Plant St. (at Driftwood Market)

  • ALL earrings BOGO
  • Raffle for a Couch Cuddle blanket (retail $95); get a ticket with each purchase of WoodStone Jewelry, or buy tickets: 1 – $1 and 6 – $5

Woof Gang Bakery | 18 E. Plant St.

  • Buy 2, Get 1 Free – Woof Gang treat bags
  • $5 Dog nail trim or grind – WALK-IN during Sidewalk Sale (reg. value: $12-$15)
  • $5 Off coupon for a full groom on a future visit (appointment required)
  • Spinning wheel for a chance to win an assortment of prizes


Summer Sidewalk Sale
Saturday, June 8, 2019
Downtown Winter Garden
FREE admission

Free parking is available throughout downtown as well as in the city’s three-level parking garage located at 160 S. Boyd St..

Visit the Facebook event page for full details.

All images courtesy of the City of Winter Garden

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