Arrival! My First Driving Tours of West Orange County- Part Two

First of all, thank you for reading the blog and for the comments. We're always please to see how interested our Winter Garden Heritage Foundation friends are in local history! There's so much to discover and appreciate.

My series of drives from the late 70s through the early 90s brought me up and down so many of the "dotted lines" in my atlas that signaled unimproved roads. Of course I thought my Volare was up to any task, but the car did become mired once in a sandy orange grove near a location on my map called Skytop; I had to get the service station down the road to come rescue me, to the tune of fifteen dollars.

Oakland and points nearby turned out to be an amateur photographer's paradise. Here are some shots preserved for forty years...

At that time, Oakland's eastern limits ended at Tildenville School Road; the border has since shifted west.

Only one of these three structures still stands:

Gone: Bill's Oakland Inn, once located at the NW corner of Oakland Avenue and Nixon Street.

Gone: This row of three shops stood at the SE corner of Oakland Avenue and Tubb Street. When I first knew it, it housed Jake Voss' antiques and collectibles collection; a small convenience store; and a hardware store operated by a Mr. Gulley after he moved here from Oakland's "downtown." At one time in the past, a filling station stood closer to the corner.

Dees Grocery stood here at the NE corner of Oakland Avenue and Tubb Street for many years. It was named the Oakland General Store when I first encountered it. The building still stands, though it is not currently occupied.

This "blue building," as people came to call it, was constructed in 1912 by J.O. Robinson after a fire destroyed the wooden buildings ranged around Oakland's Square: Grace Park. In the beginning, a hardware store operated by a Mr. Michael (later by a Mr. Gulley) shared the first floor with the Brock Grocery store; a butcher shop run by a Mr. Berry was in the rear- near the jail. Apartments occupied the second floor.

Probably the most intriguing and mysterious part of town to me was located on North Tubb Street. When I first saw this in 1978, the property was practically impenetrable, so I stayed out. This 1980s photo shows all that remained of the c.1912 Mather-Smith estate- the front gates. Compare this with the image below, made decades earlier by the Mather-Smiths:

The gate is barely seen in the foliage to the far right of the color photo above. The present owner of the property

Located on the west side is a traditionally African American community. There are at least four churches in the neighborhood, including the Trinity Missionary Baptist Church at the SE corner of Henschen Avenue and Jefferson Street.

This large house almost at the very north end of Tubb Street has had many monikers over the years, including the Williams home, the Rutherford home, the Oaktubb Inn... It began its life as a one-story structure. When it was for sale some years ago, it was referred to as the Oakhurst Estate. Currently it operates as the Oakland Manor House.

Today's Oakland Manor House

South of Oakland, I passed this group of structures at a point on the map labeled "Harlem Heights." The only Harlem I was familiar with existed in Manhattan; this turned out to be migrant housing for folks who came here from the Caribbean to harvest citrus and produce. Harlem Heights had amenities such as a post office and company store, and Harlem Heights musicians actually recorded an album of marimba tunes. Yes- we have a copy in our Heritage Museum.

Harlem Heights

This building on Oakland's West Side was originally the Oakland Elementary School for African American students. Built by the philanthropic Rosenwald family in the 1920s, who constructed thousands of similar schools mainly in the segregated South, it became a Head Start Center about sixty years later, we believe. It no longer exists.

These days, it can be a challenge to take a leisurely drive through West Orange County. The changes in the landscape due to severe citrus freezes in the 1980s has heralded a new era of growth and a markedly different landscape. It's easier to ride my bicycle, or to walk: a West Orange Trail amble from Winter Garden's Downtown Historic District to Oakland's town square is just over three miles, and well worth it. An exploration up and down the offsides streets reveals historical details and places that you might have missed while driving.

Take a break and come along with me as we discover our past!

The Winter Garden Heritage Foundation conducts walking and leisurely bicycle tours of the area by appointment. Call us at 407-656-3244 or eMail Jim at jcrescitelli@wghf.org.