Quiet Spots Along the West Orange Trail, by Jim Crescitelli

When I arrived in Central Florida in mid-1978, there wasn't much to say about West Orange County in the Howell Farms neighborhood I settled in. That's how I referred to the area in the vicinity of Semoran-436 and Howell Branch Road, which was still a location for farms, cows, and roosters crowing at sunrise. I could ride my bike ten minutes away from home and be invited into a house by a woman who wanted to show off her wood-burning stove, and walk through a grove that stretched for a block behind her barn.

Mrs. Kasik's Kitchen

Mrs. Kasik's Barn

About two weeks after I photographed her property, the barn burned down.

I bought a 1976 Plymouth Volare and ventured west after buying an Orange County road atlas at Eckerd Drugs. Always curious about my surroundings, the locales noted on the map below a rather large lake called Apopka intrigued me: Winter Garden? Oakland? Tildenville... Harlem Heights... Beulah... ? The names alone drew me out of the rapidly-expanding Orlando-Winter Park conglomerate that I called home. I began keeping newspaper clippings about the vast, grove-blanketed region that I drove to, often on bumpy two-lane roads with no dividers, and eventually started writing a Wordpress blog detailing my amateur tours; those blog posts led to the Winter Garden Heritage Foundation position I was hired for in 2012 and which I am still happily enjoying.

Today, a beautiful Sunday with temperatures in the 80s, I walked along the West Orange Trail from my office in Winter Garden three miles west to the heart of Oakland. It's still a rural adventure, though many of the secret lanes and dirt roads I used to walk along have been supplanted by blacktop streets bedecked with stop signs.

I pass by many scenes and spots which have become familiar to me, and I share them with you here. You see so much when walking the Trail, which you're apt to miss as you speed by on your bike or your skates.

Known as the Cappleman Building, thanks to the family that restored it in the late 20th. century, the 103-year-old building features these unusual tile inserts. The structure is filled with unique shops and offices that have been an important part of Plant Street's growth.

The Hugh T. Gregory American Legion Post 63 on West Plant Street was named for a World War I soldier. (His photograph graces the interior.) The exterior's "logs" that you see in the photo were installed as donors pledged funds for them to be placed during construction.

Now we're past Winter Garden's Downtown Historic District in a neighborhood known as Brayton. Its eponymous road stretches from Bay Street south to West Plant Street, and was once the site of a thriving citrus and fertilizer products stop along the Atlantic Coast Line and Tavares & Gulf railroads. Before it became the location of Maker's Hollow, the building you see here was operated by the Roper family; it housed their former Diamond R fertilizer plant, now located on Hennis Road in Winter Garden. The marquee you see in the photo once stood at the Star-Lite Drive-In Theatre, the site of today's 7/11 on West Crown Point Road and Plant Street.

Imagine what this region once looked like when citrus groves filled every available space...

The McMillan grove, a shadow of its former self, stands on the southeast corner of the West Orange Trail where it intersects with Lakeview Road. During the 20th century, the family grew and shipped citrus along with many others in the region. The site brings to mind the role that fruits and vegetables played in shaping the destiny of West Orange County.

On the McMillan property

Railroads contributed mightily to West Orange County's growth. During the middle of the 20th. century, it is said that we were the busiest region in the country regarding the shipment of perishable fruit and vegetables.

Trees growing through the rails of the Tavares & Gulf railroad tell us that a long time ago has passed since the line traveled between Tavaes and Ocoee in its mission to deliver fruit to railroads that would take it all further north. These are seen just west of the former packinghouse on Tildenville School Road; this was a spur Lin that led directly along a packinghouse owned by Clarence Tilden; the Tilden and Hurley families were major citrus growers in this area.

On the north side of the Trail, as you approach Oakland, is this mile marker denoting that this spot lies 801 railroad miles from Richmond, Virginia. Long ago it was decided that the city would serve as a central point for the rail lines passing through the eastern United States.

A former railroad section house that stands on the north side of the Trail (along the former Atlantic Coast Line tracks; it ran parallel to the Tavares & Gulf through eastern Oakland and Winter Garden). The railroad section boss lived here.

Now I'm in Oakland, three miles west of Winter Garden. The town and neighboring Tildenville were originally what drew me and my Volare and bicycle to explore and remember what I saw. How could anyone resist those beautiful old mansions?

The little shop attached to the Healthy West Orange Arts and Heritage Center at the Town of Oakland is a great spot to rest and enjoy raspberry sorbet and a bottle of water. Within your view is the 1912 Bank of Oakland, now Historic Town Hall, and I can envision what the square looked like when it was ringed by shops and offices and a hotel and an opera house. (We have hundreds of photographs at the History center that were taken over a century ago.)

This unassuming cement post is all that remains of the many that fenced off the two empty blocks west of Oakland's Town Hall. The tract was beautified as a green space by the Mather-Smith family c. 1913, and named Grace Park in the wife's honor; the fence was installed to deter wild animals from tearing up the greenery. A twelve-column pergola stretched across the center of the park- today, four columns remain.

Much of the region has changed in the 47 years that I've lived in Florida. Lush groves succumbed to 1980s freezes that changed the landscape forever; families sold properties, and homes for the vast numbers of people arriving here sprouted where orange blossoms once perfumed the air.

It's easy to step into your walking shoes and take a slow trip through history. Or, if so inclined, stop by our office and do some research about what came before today. In the Winter Garden Heritage Foundation Archive and at our two museums we pride ourselves in preserving a past that will be studied by future generations.