By Kate Cohen
Updated June 3, 2026
The idea of Orlando may conjure images of castles, coasters, and characters.
While all of those are indeed Orlando icons, The City Beautiful is also home to a variety of diverse, historic, and colorful neighborhoods well worth exploring.
Take, for example, Winter Garden, a charming small town on the west side of Orlando with a bustling main street lined in shops, cafes, and restaurants.
Beautiful fountains and landscaping divide Downtown Winter Garden’s Plant Street into two one-way lanes, adding lush tranquility and lively greenery.
This quaint Central Florida neighborhood is the perfect place to enjoy a day of shopping, dining, and other family-friendly activities that aren’t theme parks.
Here are our recommendations for six family-friendly things to do in Winter Garden.
Key Takeaways
- Spend Time in the Splash Pad
- Dine at a Family-Owned Restaurant
- Check out the Farmer's Market
- Attend a Seasonal Event
- Visit Plant St. Market
- Catch a Movie at Garden Theatre on Plant
- Stay Close to the Best of Winter Garden When You Stay at Rosen Inn Lake Buena Vista
Spend Time in the Splash Pad
In the heart of Downtown Winter Garden, you’ll find a cobblestone splash pad with a variety of jets perfect for cooling off on a hot day.
Pack your bathing suits and towels and let yourselves enjoy some refreshing playtime.
There are stone benches around the splash pad area for grown-ups who’d like to stay dry, although it’s hard to resist the temptation of cool, playful water.
Down a few steps from the splash pad is a large green area perfect for drying off, burning off some extra energy, or enjoying a post-water play picnic.
Dine at a Family-Owned Restaurant
Winter Garden is home to a variety of unique family-owned restaurants and cafes perfect for satiating any appetite.
Rosallie Le French Cafe serves delicious European-inspired pastries, salads, and artisan sandwiches in a beautiful and insta-worthy decorative setting.
Founded by two local brothers, The Whole Enchilada offers a new twist on Mexican classics. It’s also home to a fabulous rooftop area with a bar that’s perfect for dining al fresco.
The award-winning Thai Blossom Restaurant offers a menu of authentic Thai food made with fresh ingredients and served in a warm and welcoming environment.
The Deli Downtown is a sandwich shop inspired by the small-town feel of Winter Garden. It’s a great spot to pick up delicious sandwiches made with locally sourced ingredients.
In the mood for something sweet? Pick out your favorite flavor at the locally loved Scoops Old Fashioned Ice Cream Store or Kelly’s Homemade Ice Cream.
Southern Home Bakery is known for their stylish sugar cookies and Sweetland Bakery and Tea House is the perfect place for pastries and sweet milk tea.
Check out the Farmer’s Market
The Winter Garden Farmer’s Market is an award-winning community event held every Saturday from 8 a.m. to 1 p.m.
Held year-round, over 100 vendors come together to sell goods like locally sourced produce, artwork, baked goods, seasonal items, artisan crafts, apparel, and so much more.
Every week, the farmer’s market hosts live music and on select dates, you’ll find free special event programming like kid's crafts, lawn games, and other entertainment.
Whether you’re shopping with a list or just looking to peruse local treasures, the Winter Park Farmer’s Market is the perfect place to spend a Saturday morning.
Attend a Seasonal Event
Throughout the year, Downtown Winter Garden hosts a variety of seasonal events and celebrations that are open to the public.
From mid to late October, Winter Garden transforms for Halloween with a spooky light show projected on City Hall, live shows and pop-up street performers, trunk or treat events, street sales, and other autumnal activities.
During the winter holidays, festive vibes take over the town with millions of twinkling lights, horse-drawn carriage tours, decorative displays, and plenty of holiday entertainment.
Celebrate Independence Day with their annual All American Kids Parade and Pancake Breakfast followed by a patriotic party complete with concerts, crafts, and of course, fireworks.
You’ll also find community events celebrating holidays like Juneteenth, Martin Luther King Jr. Day, and the first day of spring.
Check Downtown Winter Garden’s event calendar prior to your visit to see what’s happening while you’re in town.
Visit Plant St. Market
At the far end of Plant Street in Downtown Winter Garden is Plant St. Market, an indoor marketplace with a variety of vendors selling food and artisan specialty goods.
It’s also home to Crooked Can Brewing Company, giving grown-ups the perfect opportunity to enjoy a refreshing beer brewed onsite.
Treat yourself to something delicious and enjoy spending quality time on the pet-friendly patio, which often hosts live music and entertainment.
This bustling venue is a popular spot for spending quality time while supporting local businesses within the Winter Garden community.
Catch a Movie at Garden Theatre on Plant
In the center of Downtown Winter Garden is Garden Theatre on Plant, an intimate and historic theatre that has been a beacon of the small town since 1935.
The refurbished theatre hosts theatrical performances, concerts, and other events.
It’s also a great spot to catch a featured showing of a family-friendly movie for only $5 per ticket.
In summer 2026, you can look forward to movies like Zootopia 2, Spaceballs, The Sandlot, How to Train Your Dragon, Ferris Bueller’s Day Off, Boss Baby, and other entertaining titles.
In the fall, you’ll find a lineup of scary movies and family-friendly frights, while the holidays usher in classic Christmas films perfect for creating a new family tradition.
Check the theatre’s schedule online to see what’s showing soon and purchase your tickets in advance.
Stay Close to the Best of Winter Garden When You Stay at Rosen Inn Lake Buena Vista
Coming to Orlando for a visit? Let Rosen Inn Lake Buena Vista be your home away from home.
Centrally located in Orlando’s entertainment district, our hotel is minutes away from the world’s most famous theme parks as well as a variety of Central Florida’s hidden gems like Winter Garden.
Spend your spare time lounging by the pool (did we mention we have two?) or playing in our colorful onsite splash pad with the kids.
At the end of every night, enjoy a good night’s rest in your spacious and comfortable hotel room, equipped with all the amenities you need for an incredible family vacation.
We look forward to hosting you for your next Orlando adventure.