Oakland History

Nearly 130 years ago, Oakland was the industrial and social hub of Orange County. Now, only remnants of that heydey remain in this serene, unspoiled hamlet that was a booming railroad town in the late 1800s. Some of the houses built for railroad officials and workmen still dot its oak-lined clay roads. Old railroad tracks (now the West Orange Trail) and a few buildings constructed after a fire that virtually destroyed the flourishing business district reveal a glimpse of an Oakland that used to be. An inn, later converted to a house, was the site of the first schoolhouse. The 121 year old structure still stands.

This quaint town of nearly 3,000 residents lies about 2 miles west of Winter Garden on the southern shores of Lake Apopka. “Oakland became the center of Orange County’s social and economic life with people of wealth and fashion coming to the hotel and neighboring homes for the winter social season,” wrote author Eve Bacon in a book entitled Oakland, the Early Years, which traces the town’s history. “If it had not been for the failure of the railroad, Oakland may well have become the population center of Orange County.”


By 1860, the unincorporated community, named for the native oaks that grew so profusely in the area, already had a post office, a sugar mill, gristmill and sawmill. “It was a busy industrial center for that early date,” Bacon said. However, Oakland’s ready access to faster transportation routes sparked the town’s rapid growth and catapulted it into a prominent position in Central Florida. “Transportation was the great problem of the early pioneer growers. How to get their products to market became the major consideration of the growers,” Bacon said. The completion in 1887 of a canal provided a direct water route to Sanford where produce was loaded on boats for shipment to Northern markets. It eliminated the need for the slower ox cart for wagon for overland shipping.


In 1886, Oakland’s founder, Orange County Judge James Speer, opened the way for the railroad, which bought Oakland its biggest boom. He persuaded officials of the Orange Belt Line Railroad to swing the tracks through the community when he heard that lines would be laid to the south side of Lake Apopka. Peter Demens, the railroad’s largest investor, and the man who later became Oakland’s first mayor, agreed to run the tracks in exchange for Speer’s offer to donate 200 acres of land along the lake’s southern shores.

In 1891, the area officially became the Town of Oakland. Speer designated 180 acres for a townsite, 15 acres for a depot and railroad shops and 5 acres for a park. Demens, a Russian immigrant, had wanted to name the newly incorporated town St. Petersburg after his birthplace in Russia. But the people preferred the name Oakland as the community always had been called. With the arrival of the railroad, “Oakland became the headquarters of the Orange Belt Investment Co. and the town began to boom. The boom years between 1880 and 1890 were Oakland’s greatest years,” Bacon wrote. During that period, hotels, stores, offices, a telegraph office, a hospital, a newspaper and opera house sprouted in town. Around 1890, Oakland for another railroad, the Tavares and Gulf, tagged the “Tug and Grunt” because of its performance. “The railroad was a major influence. They built most everything in Oakland. The people from the railroad were the officials of the town,” recalled Louise Battin whose maternal grandparents were early settlers.

The Union Club

The town’s social life revolved around the Union Club. “Known as the Opera House, plays and theatricals featuring well-known actors and actresses were held in the upper floor of the building. The lower floor was reserved for parties, banquets, the famed masquerade balls and dancing,” Bacon said. Oakland’s prosperity came to a grinding halt when a fire destroyed its downtown and the railroad pulled out because of a sharp slump in business.

Close-Knit Town

A severe freeze in 1894-95 killed most of the citrus groves, leaving the Orange Belt Line with almost no freight to ship. Shortly afterwards, the firm leased its lines to another railroad company. When stores and shops built by the railroad closed, Oakland settled back into life as a quiet agricultural community. But a fire that swept through the town in the late 1890s broke the community’s economic back. By choice, the bustle of that earlier time never was recaptured. So Oakland remains a quiet, unpretentious, close-knit town, many of whose residents are descendants of the original settlers. With their strong spirit of volunteerism that has helped hold the town together, residents ardently cling to the small-town way of life. Residents enjoy rural living, few paved roads, and the absence of noisy apartment complexes. Residents like the down-home atmosphere their town offers and the camaraderie that exists among them.

Valerie Anderson
Orlando Sentinel
11 October 1982