Visit The Charming City With A Juicy Past!

Expert View Column
Visit The Charming City With A Juicy Past!
By ATD’s Florida Experts Simon & Susan Veness
Are you ready for the latest ‘insider’ tip on where to go in the Orlando area for a real locals’ experience? Well follow us to Winter Garden and we’ll show you why this is one of the most up-and-coming places to explore for unique shopping and dining – and explain why it calls itself ‘the charming city with a juicy past!’.

This vast region that we call Orlando is really made up of a whole series of towns and cities that all get lumped together as part of the greater metropolitan area and, if you stick just to the theme parks, you will actually see none of it.


Winter Garden


That’s why we like to encourage visitors to travel a bit further afield and really see some of the Florida they have just flown 4,000 miles to visit. Places like Winter Garden, which is just 15 miles north of Walt Disney World, 18 miles north-west of Universal Orlando, and easy to find just off the (toll) Western Beltway (Highway 429). From the Kissimmee area, take Highway 192 to the 429 and just go straight north; from Disney, take State Road 535 (Winter Garden-Vineland Rd); or from International Drive and Universal, go via the Florida Turnpike.

If you go via the 429, you can come off at exit 19 for Winter Garden Village, which is a huge area of modern shopping and restaurants in an open-air plaza grouped around the big-box stores of Target, Marshalls, Best Buy, World Market and Sports Authority. There is also some good dining choice, such as Uno Pizzeria & Grill, Bonefish Grill, Longhorn Steakhouse and (Simon’s favourite), the great burgers of Red Robin.


Winter Garden


But, despite the name, this is not actually the city of Winter Garden. You either need to get back on the 429 or follow Daniels Road another three miles north, which will bring you to the village-style ‘city,’ which sits almost on the shore of Lake Apopka (which is the biggest lake you see if you fly in from the north of Orlando).

The ‘downtown historic district’ consists of just seven blocks stretched along Plant Street, but it is packed with interest and is a wonderfully pretty location that evokes the traditional feel of small-town America. The ‘historic’ part dates back to the early 1900s and it is listed on the US Register of Historic Places.

The main street is bisected by the West Orange Trail and features brick-paved roads, pleasant walkways, swing-seats and fountains, as well as the Downtown Pavilion, with its inviting pop-jets for kids to play in.

Winter garden


It all starts at the quaint Visitor Center and Heritage Museum (1-5pm daily), which was originally the 1918 train station on the Atlantic Coast Railroad. It is free to enter (although they do ask for a small donation to the Winter Garden Heritage Foundation) to look through their collection of exhibits, Native American artefacts and memorabilia, which sets the period scene for the story of Winter Garden as part of the thriving citrus industry in Central Florida, which was actually the world’s largest citrus shipping center in the 1940s, sending out huge quantities of oranges and orange juice (hence the ‘juicy city’ tagline!).

Also here is the Central Florida Railroad Museum (also part of the Heritage Foundation), which features a look back at the huge role the railroads had in the development of the region.


Winter Garden


Another highlight is the thoroughly cute Garden Theater, which dates back to 1935 and has been restored and hosts the performing arts – including the Orlando Ballet Company – as well as films and other special events.

The real draw here, though, is the array of shops, cafes, bars and restaurants which line both sides of Plant Street, providing a great amenity for locals and visitors alike. And Winter Garden is fast developing a real cult status with the locals as it comes back to life following a period in the 1980s and 90s when it was all but extinct.

Here you will find a tempting array of boutique shops and galleries that are about a million miles from the usual tourist fare and which reward the casual browser. Take your pick from Mr Bee’s Popcorn & Candy Shop, Anne’s Art & Design, Grace’s Gifts, The Sacred Olive, Kaebisch Chocolate, Wildflower Beauty and the wonderful cakes of Sweet Ashley Rae’s, plus several salons and a music store.


Winter Garden


Then, for a quick drink or snack, there are Axum Coffee, Sweet Traditions Bakery & Café, JoJo Smoothies and Scoops Old Fashioned Ice Cream Parlor, as well as 10 fully-fledged restaurants, that run the choice from Winter Garden Pizza Co and Harry & Larry’s Bar-B-Que, to high quality oriental choice at Thai Blossom Café, fine Mediterranean dining at Al Fresco and the upmarket The Chef’s Table & Tasting Room, which brings foodies from all over town.

It makes for a lively and bustling scene in the evening and weekends, while the newest element of the Winter Garden scene is arguably the most enticing, especially for an afternoon’s shopping followed by a few drinks.



The Plant Street Market opened in May this year and is a fabulous mix of 18 food and lifestyle vendors in a market-style setting, all inside a mock Victorian brick building that is as good on the inside as it is eye-catching outside. Here you will find fine teas and coffees, a local butcher, several arts and crafts stalls, a baker’s, a chocolatier and more, including the excellent Crooked Can Brewery, which brings in beer fans from far and wide.



The variety is terrific and, if you like the beer choice, there are 32 and 64oz ‘growlers’ to take home with you afterwards! It is all hugely imaginative and adds a real bohemian touch to the Main Street scenario, a 21st century feel for the small-town America style. The Market is open 9am-7pm Mon-Sat (11am-6pm Sun), while the Crooked Can is open 11am-11pm Sun-Thur and 11am-2am Fri and Sat.

And that’s not all. Winter Garden is also home to a Saturday Farmers Market(9am-2pm each week), with live music, arts and crafts, as well as a series of festivals through the year, notably the Corn Harvest Festival (early November), Spring Fever (April), MusicFest (October), a Christmas Parade and a huge 4th of July Party in the Park.



If you enjoy cycling, the city is right on the 22-mile West Orange Trail, and you can rent bikes here to cruise along the Trail from either West Orange Bike or Wheelworks.

Stop in at the Visitor Center and you can also pick up maps for the West Orange Trail, the North Shore Restoration Area (a lovely lakeside walk from Magnolia Park, varying from 4 to 14.6 miles in length), and the Green Mountain Scenic Byway, a gentle car drive around much of Lake Apopka.

It all adds up to authentic slice of Florida that is close to the theme parks yet light years from the hustle and bustle. Just tell them Simon and Susan sent you!

Do you have questions on this story or anything to do with Orlando or Florida? Be sure to join Susan and Simon on the fabulous ATD discussion forum here.

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