The Old Florida Side of Orlando: Citrus Roads, Lake Towns, and Historic Corridors

Most visitors know Orlando for its theme parks and sprawling resorts. But beyond the turnstiles and traffic, the region holds an older story—one shaped by citrus groves, freshwater lakes, and towns that predate the modern skyline. Exploring the Old Florida side of Orlando means tracing the backroads, pausing in small communities, and noticing the subtle transitions from pine flatwoods to rolling citrus country. This guide offers a grounded look at the area’s historic corridors, rural byways, and lakefront towns that still reflect Central Florida’s original character.

Understanding Old Florida in the Orlando Region

Orlando sits at the heart of Central Florida, a region once dominated by citrus, cattle, and freshwater lakes. Before the city’s explosive growth in the late twentieth century, the area was a patchwork of groves, small towns, and railroad stops. Many of these places remain, tucked between newer developments or radiating from the city’s original core. Exploring them offers a different pace and a deeper sense of place than the city’s better-known attractions.

Citrus Roads: Remnants of the Orange Belt

The legacy of citrus runs deep in Central Florida. While freezes and development have reduced the number of working groves, you can still find pockets of citrus country west and south of Orlando. Roads like Orange Avenue, Old Winter Garden Road, and Lake Apopka Loop Road trace the old citrus belt, passing remnants of packing houses, roadside stands, and the occasional surviving grove.

Driving the Citrus Corridors

• Lake County’s Ridge: The rolling hills northwest of Orlando, especially around Clermont and Montverde, once held some of the state’s most productive groves. The area’s sandy ridges and scattered lakes made it ideal for citrus. Today, you’ll spot old packing sheds and the occasional fruit stand along County Road 561 and State Road 50.
• State Road 19: North of Howey-in-the-Hills, this route offers glimpses of remaining groves and views across Little Lake Harris. The town of Howey itself was founded as a citrus community in the 1920s.
• Orange Avenue: South of downtown Orlando, Orange Avenue traces a historic route through Pine Castle and Taft, areas that once supplied fruit to the city’s early residents.

Winter and early spring are the best times to catch the scent of citrus blossoms along these byways. While many groves are private property, some farm stands still operate seasonally—call ahead or check local listings for current hours and access.

Lake Towns: From Resort Era to Present

Central Florida’s lakes have always shaped settlement patterns. Before the era of air conditioning, lakeside towns like Winter Park, Mount Dora, and Eustis drew visitors seeking cool breezes and scenic views. Many of these communities retain their historic downtowns, with brick streets, old hotels, and waterfront parks.

Winter Park: Canals, Cottages, and College

Just north of downtown Orlando, Winter Park was founded in the 1880s as a resort community. Its chain of lakes is connected by narrow canals, which you can explore by scenic boat tour or from public parks. The city’s downtown, centered on Park Avenue, features historic storefronts and tree-shaded sidewalks. Rollins College, Florida’s oldest recognized college, anchors the south end of town and adds to the area’s architectural interest.

Mount Dora: High Ground and Historic Charm

Perched on a ridge above Lake Dora, this town grew around a steamboat landing and later became known for its arts festivals and antique shops. Mount Dora’s historic district is walkable, with preserved homes and a waterfront park that offers views across the lake. The old Atlantic Coast Line Railroad depot still stands, a reminder of the area’s role as a transportation hub.

Eustis and Tavares: Lakeside Rail Towns

East of Mount Dora, Eustis and Tavares both developed along the shores of Lake Eustis and Lake Dora. These towns were once stops on the “Orange Blossom Special” rail line, and their downtowns still reflect that era. Tavares has branded itself as “America’s Seaplane City,” with a public seaplane base and a small marina park. Eustis offers a historic lakefront and a walkable core with early twentieth-century architecture.

Historic Corridors: Roads That Reveal the Past

Several old routes cut through the Orlando region, connecting early settlements and agricultural areas. Driving these corridors gives a sense of the area’s changing landscape and the persistence of older communities.

Old Winter Garden Road

This east-west route traces the path of early settlers moving between Orlando and the agricultural town of Winter Garden. While much of the road is now suburban, the western stretches still pass older neighborhoods, historic churches, and citrus-era landmarks. Winter Garden’s downtown, with its brick streets and restored railroad depot, is a focal point for local history.

State Road 50: The Cross-Florida Highway

Running from the Atlantic coast to the Gulf, State Road 50 has long served as a main artery through Central Florida. West of Orlando, it passes through Ocoee, Winter Garden, and Clermont—each with their own historic districts and reminders of earlier eras. The road’s alignment often follows old rail lines and stagecoach routes, especially in the rural stretches west of the city.

U.S. Highway 441: The Orange Blossom Trail

Known locally as Orange Blossom Trail, this north-south route was once the primary highway through the region. While much of it is now commercial, sections north of Orlando pass through older communities like Apopka and Zellwood, where traces of the area’s agricultural past remain. In the early twentieth century, this corridor connected citrus groves, truck farms, and small towns to the markets of Orlando and beyond.

Planning a Trip: Practical Tips for Exploring Old Florida Orlando

• Transportation: A car is essential for exploring most of these areas. Many of the best drives follow secondary roads and require some navigation. Some towns, like Winter Park and Mount Dora, are walkable once you arrive.
• Seasonal Considerations: Citrus groves are most active from late fall through early spring. Festivals and farmers markets in lake towns often take place in the winter and spring months. Summers can be hot and humid, with frequent afternoon storms.
• Historic Sites and Museums: Many towns have small local museums or historical societies. Hours and access can vary, so it’s best to check ahead before planning a visit.
• Dining and Local Produce: Farm stands, local diners, and small-town cafes are part of the experience. In season, look for fresh citrus, local honey, and other regional specialties.
• Events: Annual festivals—such as the Mount Dora Arts Festival or Winter Garden’s spring events—offer a window into the community spirit and history of these towns.

Always verify current hours, access, and conditions before visiting, as some historic sites and businesses may have limited or seasonal operations.

Connecting the Past and Present: Why Old Florida Matters

Orlando’s rapid growth has transformed much of Central Florida, but the region’s older layers are still visible for those who look. The citrus roads, lake towns, and historic corridors described here offer a way to experience the area’s original character—one shaped by geography, agriculture, and small-town life. Whether you’re a local or a visitor, taking the time to explore these places adds depth and context to any trip through Central Florida.

Suggested Itineraries and Routes

• Half-Day Lake Town Loop: Start in Winter Park, explore Park Avenue and the lakes, then drive north to Mount Dora via U.S. Highway 441. Stroll Mount Dora’s downtown and lakefront, then return via Eustis and Tavares.
• Citrus Country Drive: Begin in Clermont, follow County Road 561 north through Montverde and Howey-in-the-Hills, then loop back via State Road 19. Stop at roadside fruit stands if open.
• Historic Corridor Tour: Trace Old Winter Garden Road from Orlando to Winter Garden, pausing in Ocoee for a look at its historic core. Continue west on State Road 50 toward Clermont for rolling views and reminders of the old citrus belt.

Each route offers a different perspective on the Old Florida side of Orlando—one that rewards curiosity and a slower pace. Bring a map, check local resources for current information, and allow time to stop in small towns along the way.

Resources for Further Exploration

• Local historical societies and museums in Winter Garden, Mount Dora, and Winter Park
• Seasonal farmers markets and citrus stands (availability varies—verify before visiting)
• Scenic boat tours in Winter Park and Mount Dora
• Regional visitor centers for updated maps and event information

Exploring the Old Florida side of Orlando takes you beyond the usual itinerary. With a bit of planning and a willingness to follow the backroads, you’ll find a region where the past is still present—waiting to be discovered, one citrus road or lake town at a time.