SPONSORED — Thoughts turn to the holidays–and shopping–as soon as Thanksgiving is over, and Downtown Winter Garden’s Small Business Saturday event on Saturday, November 30, 2019 is the ideal place to launch this year’s holiday memories.

Known for its quaint charm, Winter Garden is teeming with unique independently-owned shops that will take the nationally-observed Small Business Saturday to new heights with this all-day event from 10am -7pm. Kick off your holiday shopping with great sales, nearly 60 raffle giveaways and free live music in the festive wonderland of historic Downtown Winter Garden.

Make a day of it by strolling the brick-lined streets for special deals and discounts, stopping at one of the one-of-a-kind restaurants for delicious food and drinks (and special offers!), pulling up a seat at an outdoor patio to enjoy the live music, and checking out the holiday-themed decor throughout downtown.


Top-notch musicians will perform live at the Centennial Plaza Gazebo throughout the day. Teddy Henderson, a Disney Springs crowd favorite, launches the festivities at 11am. The three-member Mud Rooster band will follow to entertain the crowd from 3:30-7 pm.

Live music schedule:

  • Teddy Henderson, 11am – 2:30pm
  • Mud Rooster, 3:30 – 7pm

Mud Rooster


A huge raffle with free giveaways from more than 50 downtown businesses will add to the day’s festivities. Prizes include gift cards, gift baskets, free merchandise and more.

Shoppers can visit any of the raffle participants to obtain raffle tickets (parameters for distribution are set by each individual business). Raffle tickets will be collected at the centrally-located Centennial Plaza for a one-time raffle drawing conducted at 5pm. Winners do not need to be present to win.

Raffle participants include:


Burger Fi | 360 W. Plant St.

  • Free French fry with purchase of a sandwich and a drink

Crooked Can Brewing Company | 426 W. Plant St.

  • Special beer release: Toastmaster Bourbon Barrel Aged, Russian Imperial Stout will be available on Small Business Saturday (Nov. 30)! This unique bottle release of the Crooked Can Cork Series has a very limited availability and makes a great holiday gift for craft beer lovers.

The Deli Downtown | 18 N. Boyd St.

  • One FREE mimosa for every sandwich purchased for the first 50 customers (21 years old or older)

Divine Wellness | 33 S. Main St.

  • 20% off the following brands: Root Nutritionals, CBD, Filthy Farm Girl, Nature’s Sunshine Produsts, Europharma, Barleans Organic Oils, Gemstones & Jewelry

Doxology | 49 S. Main St.

  • Storewide specials and discounts
  • Gift with purchase


Driftwood Market | 46 W Plant St.

  • 70% off select items
  • Sips, snacks, giveaways and gifts with purchase

Garden Theatre 160 W. Plant St.

  • Purchase tickets for 3 shows in Garden Theatre’s 2019-20 season with a 3-Show pack: $84.00 – a 25% discount!

KITLIFE | 100 S. Boyd St.

  • 20% off storewide

Melts on Main | 108 S. Main St.

  • Buy one Melt Sandwich, get one 50% off

Shoo Shoo Baby | 117 S. Boyd St.

  • Free pair of leggings with any $50 purchase
  • $25 door buster deals

Shoo Shoo Baby

Sweet Dee's Cupcakery | 21 S. Main St.

  • 20% OFF All In-Store Purchases (no custom orders)

Urban Flats | 132 W. Plant St.

  • Free $10 bonus gift card for each $50 gift card purchase

Way Chocolate & Coffee | 50 W. Plant St.

  • Buy One, Get One FREE Mini Brigadeiro Cupcakes

Winter Garden Wheel Works | 101 W. Plant St.

  • Everything on sale, including bikes up to 40% off
  • BOGO accessory deals
  • Free kid's helmet with bike purchase

Winter Garden Wheel Works


Winter Garden Small Business Saturday
Saturday, November 30, 2019
Downtown Winter Garden
FREE admission

Free parking is available 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.

Winter Garden Small Business Saturday 2019

All images courtesy of the City of Winter Garden

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