Tampa Bay Sports and Entertainment is always looking for worthwhile day trips for readers who want to explore beyond the coast. Although Florida is known for its beautiful beaches, the center of the state offers its own appeal in small towns such as Winter Garden. Located on Lake Apopka, about 30 minutes from Orlando and Walt Disney World, Winter Garden blends historic character, boutique shopping, restaurants, and outdoor recreation into an easy Central Florida getaway.
Like many small towns in Central Florida, Winter Garden grew from an agricultural economy, especially the citrus industry that shaped Orange County through much of the 19th and 20th centuries. The arrival of the narrow-gauge Orange Belt Railway in the 1880s accelerated the town’s growth, drawing stores and businesses to Plant Street, which paralleled the tracks and later became the core of today’s historic downtown. When difficult years in the citrus industry weakened the local economy, town officials redirected Winter Garden toward the charming, tree-lined shopping and tourist destination it is today.
Plant Street and its cross streets, from Central Avenue to Dillard Street, form the heart of the historic downtown, with Victorian-era red-brick buildings and vintage tin-tile ceilings. Although car traffic is allowed along brick-paved Plant Street, the area is especially pedestrian-friendly near its center, west of Main Street, where Centennial Plaza offers a grassy gathering space with a clock tower, an ornate tiled fountain, and a gazebo stage for live entertainment. For history buffs, Winter Garden’s historic train station on Plant Street has been converted into the Winter Garden Heritage Museum, while the Central Florida Railroad Museum sits at the corner of South Boyd and Tremaine Streets.
A good visit can be built around Plant Street: start with a walk through the historic downtown, stop at the museums or the farmers market if they fit your schedule, then leave time for lunch, shopping, and a ride or walk along the West Orange Trail.
Shoppers have plenty of opportunities to indulge themselves, including the Plant Street Market, an indoor market featuring handmade items and homemade foods, and the year-round Winter Garden Farmers Market, which brings more than 100 vendors downtown on Saturdays. The historic buildings converted into chic boutiques and restaurants are also not to be missed. Together, the preserved architecture and active storefronts give Winter Garden the feel of a historic town that still has plenty of modern energy.
Winter Garden is also a destination for visitors who enjoy nature and outdoor sports. Beyond the linear park feel of Plant Street, the town has green spaces and athletic fields, including Dr. Bradford Park and Newton Park a few blocks north on the shore of Lake Apopka. Although the immediate downtown area is easy to explore on foot, the best way to take in more of the area is by bicycle. Local communities converted the unused Orange Belt Railroad railbed into a public trail for walking, running, and bicycling. Twenty-two miles of the old rail line have been paved, beginning in nearby Oakland, passing through Winter Garden, and ending in Apopka. A bicycle shop on Plant Street, right off the trail, will rent or sell you a bicycle if you have not brought your own.
Winter Garden is a charming historic town near Orlando with more to offer than a quick stroll through its downtown. As accessible from the Tampa Bay area as Orlando or Walt Disney World, it makes a rewarding day trip for boutique shopping, restaurants, live entertainment, local history, and time outdoors.
For more information: City of Winter Garden website: https://www.cwgdn.com/