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City of Winter Garden presents: Shop, Dine, & Stroll – March 27th

City of Winter Garden presents: Shop, Dine, & Stroll – March 27th

Sidewalk Sale in Celebration of National Mom and Pop Business Owners Day!
All-Day (Open to Close)
Location: Winter Garden Downtown Historic District, 300 W. Plant St.

The Love Local campaign, launched by the City of Winter Garden last fall, continues in 2021 with a line-up of programs and activities to help small businesses recover from financial losses due to the COVID-19 pandemic. The intent of the Love Local campaign is to build awareness of the importance of shopping and dining local to support small businesses and community organizations that are vital to the city.

Winter Garden is well-known for its small town charm – and it’s no surprise with the plethora of mature trees and beautiful flowers to the authentic historic brick buildings that line the city’s downtown area. Winter Garden also features an award-winning farmers market and is home to many one-of-a-kind locally owned restaurants, unique shops, art, and entertainment. Local businesses are the heart and soul of Winter Garden, and they need our support.

Each and every one of us can have an impact. Every time you make a purchase, you are making an impact. Choose to go to a local restaurant over a national chain. Shop at local boutiques instead of big-box retailers. Shopping online and at national chains is convenient, but when you support local businesses, you are strengthening the backbone of a community. According to the organization Independent We Stand, for every $100 spent at local businesses, $68 will stay in the community. Whereas only $43 remains in the community when shopping at a national chain.

From now through the summer, the Love Local campaign will include monthly activities and programs that support local businesses and community organizations and on Saturday,
March 27th, Downtown Winter Garden and Citywide will celebrate “Shop, Dine, & Stroll”.

Shop, Dine, & Stroll – Saturday, March 27th

In celebration of National Mom and Pop Business Owners Day, come out to an outdoor shopping and dining experience to support the independently owned businesses that make Downtown Winter Garden so unique! The nationally observed holiday serves an even greater purpose this year as small businesses strive to recover from the pandemic.

March’s ideal weather makes it the perfect time to stroll the charming streets, shops, and outdoor dining areas. Peruse the outdoor sales racks, fresh spring apparel, accessories and home goods to get ready for the new season. The independently owned shops will also feature in-store and online specials/promotions, as well as curbside delivery.

Take a shopping break to enjoy freshly prepared menu items and beverages at Downtown’s one-of-a-kind eateries, and grab a seat at one of the many outdoor umbrella tables that line the historic streets to enjoy a side of Florida sunshine.

Shop, Dine & Stroll will be held rain or shine. Sales, special offers, delivery methods, and operating hours vary per merchant. For more information, visit

A Preview of Shop, Dine & Stroll special offers and seasonal menus include…


21 S. Main St.

Featuring an assortment of popular Easter cupcakes this year including
carrot cake, Cadbury Easter basket, marshmallow peeps, and carrots and dirt, plus
a few new offerings this year!
– Paint your own sugar cookie egg kits
-“Carrot” Chocolate Dipped Strawberries
-Carrot and Dirt Pudding Cups

121 S. Boyd St.

Special Offers/Seasonal Menu:

“Angels & Demons” combo for $5 on 3/27 from 11am to 4pm
New sandwich and salad as a combo — something very good for you and another just…let’s just say thoughtfully sourced and leave it at that!

“Who’s Your Daddy?”
Shaved all beef bologna sautéed until it has some crisp parts. Topped with American Cheese, Fritos, Yellow Mustard and served on a locally baked ciabatta roll.

“Flower Child”
Locally sourced sprouts tossed with baby arugula in a maple vinaigrette topped with shredded beets, orange/yellow bell peppers, cucumbers, radishes, goat cheese and EDIBLE locally grown nasturtiums and broccoli flowers.

99 W. Plant St.

The Tasting Room and Chefs Table has a spring salad featuring Kalera Farms baby romaine,
heirloom tomatoes, lardons, Parmesan crisp, tarragon croutons and black garlic dressing.

We’ve got comfort food covered with our spring desserts:
Florida peach upside down cake with peach caramel and house vanilla bean ice cream.

Our spring fruit crumble dancing on the palate with macerated Florida berries, oatmeal streusel and vanilla bean ice cream.

28 W. Plant St.

The Attic Door will offer a full afternoon tea experience, reservations required by calling 407-750-7063, and will feature some of the fresh produce in Florida including our very popular Florida cucumber cream cheese sandwiches and a savory Florida spinach & artichoke cup.

Our evening menu features fresh Florida tomatoes on our house bruschetta and other fun snacks, sliders and entrees.


137 W. Plant St.

Join us during the Shop, Dine & Stroll and meet some of our talented members in person! We will also have one of our local artists on hand for individual signings. This event is a great opportunity to see all of our spring arrivals, including brand new spring floral arrangements and larger-than-life special edition Easter Peeps!

32 W. Plant St.

Promotion for Shop, Dine, & Stroll:
Free tote with a $75.00 purchase

Serving the Orlando area since 2014, Writer’s Block Bookstore is Central Florida’s full- service independent bookstore with locations in Winter Park and in Winter Garden. We specialize in new releases, New York Times best-sellers, Indie Next picks, and unique gifts and puzzles. We routinely host virtual and in-store author events with nationally recognized authors and offer discounts for educators and loyalty club members.

With new titles and merchandise hitting our shelves weekly, there is always something new to discover!

Writer’s Block commitment to literacy, reading, and community engagement for life-long learning is showcased through its events, book clubs, virtual book fairs, online Sunshine State and children book lists, and community partnerships.

117 S. Boyd St.

Promotion for Shop, Dine & Stroll:
20% off storewide and additional sale racks of $20 and $30 items.
Shoo Shoo Baby Boutique is a women’s clothing boutique
in downtown Winter Garden, named after the World War II plane
of Natalie, the store owner’s, father-in-law.


The Downtown Winter Garden Curbside Program provides complimentary contact-free delivery of purchases from both shops and restaurants to the comfort and safety of your vehicle parked throughout downtown.

Sponsored by the City of Winter Garden, call Downtown Ambassadors at 407-576-1421, 1422, and 1423 to alert of your arrival and parking zone.

Winter Garden Farmers Market
8:00 am – 1:00 pm
Downtown Pavilion, 104. S. Lakeview Ave.

Expand your support of independent business owners to the farmers and vendors at the
Winter Garden Farmers Market – happening the same time as Shop, Dine & Stroll.

Convenient parking is always free throughout Downtown Winter Garden, including in its three-level parking garage, 160 S. Boyd Street.

For more information about Downtown Winter Garden, please visit

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