Oakland Timeline


The first post office was established, and William C. Roper was postmaster.

A two-story inn was built at a midway point on the trail between Sanford (then called Mellonville) and Tampa. James Speer, who was moving back to Texas, sold his holdings in Oakland to Dr. Buford, who then sold them to James Jackson.


The post office closed. Speer returned to Oakland and bought 1,000 acres from Dr. J.D. Starke of Ocoee.


Speer became the largest landowner in Central Florida when Jackson, his wife’s father, died and Speer bought the land from the other heirs.


Speer reopened the post office as postmaster. Other pioneers of the day were Luther Fuller Tilden and George Frank Connell, farmers; and James E Willis, farmer and citrus grower.


A charter was issued for the Orange Belt Railroad, which was to run from Lake Monroe to Lake Apopka. A second railroad, the Tavares, Apopka and Gulf, was started with tracks that began at Ellsworth Junction near Tavares.


The Orange Belt was purchased, and tracks were laid on a path toward Lake Apopka. Speer offered 200 acres on the south shore of Lake Apopka (half interest in 180 acres plus 15 acres for railroad shops and a depot and five acres for a town park) if the owners would swing the railroad line into Oakland. An agreement was reached. The rails reached the town later that year, and the first train arrived in Oakland in great celebration. John Carlson was the engineer of that first train.

Once the depot was built, the business section was established with a hotel, hospital, opera house, grocery, hardware store and offices.

Thomas Jefferson Appleyard started publishing the first newspaper of the area, a weekly called The Southern Sun.


A meeting was called to incorporate the town with 31 qualified voters listed. Peter A. Demens was elected the first mayor. Others elected were J.F. Bedford, A.J. Grant, a.m. Taylor, Henry Kaufmann and G.D. Ackerly as aldermen; F.E. Eastman as city marshal; and WP. Gilkeson as city clerk. The Presbyterian Church was organized.


James Orlando Brock was proprietor of the Oakland grocery. The Town Council created the positions of tax assessor, city marshal and tax collector.


The first black school opened in Oakland. William Bourne was station agent.


A new two-story schoolhouse was built just west of the Presbyterian Church. The Oakland Cemetery Association was formed. A large city park was developed.


The Florida Legislature legalized incorporation of the town of Oakland. The first mayor, Demens, a Russian immigrant, wanted to name it St. Petersburg, after his birthplace, but the residents insisted on keeping the name Oakland because it reflected the town’s beautiful canopy of oak trees. (Demens’ Russian roots were evident in the architectural style of the Orange Belt Railroad Depot.)

There was a confrontation between the two railroads when the TAG rails were laid nearly to Oakland and the Orange Belt threatened TAG with an injunction to keep it out of town. However, the TAG took advantage of a Monday holiday and ran the tracks along what is now Arrington Street. All the track was laid by the time courts opened Tuesday. A month later, a passenger and mixed train was running daily in each direction. The TAG later reorganized as the Tavares and Gulf Railroad.


Judge James G. Speer died. The Orange Belt Railroad reorganized as the Sanford and St. Petersburg Railroad.


The black school closed.


In this year of the “Big Freeze,” the Sanford and St. Petersburg line was sold to the Plant System because of a decline in freight along the line.


The town’s population dropped to about 200.


The Oakland jail was a wooden building behind the hardware store.


An official post office building was built near Grace Park. Prior to this, the post office was temporarily set up in a number of locations, including several postmasters’ homes and the Connell and Brock stores.

An Episcopal Chapel was built near the town’s hotel.


The black school reopened.


The South Lake Citrus Growers Association was organized.


The Angebilt Lodge, also called the Oakland Hotel, was built on what is now Tubb Street. It was attached to a home built in 1890 that was used as the hotel dining room. Rooms were $3 a day.

A Missionary Baptist Church was erected at the west end of town.

The Masonic Lodge, on the corner of Hull and Walker streets, was used as a school for black children.

A few homes had electric lights from power furnished by the South Lake Apopka packinghouse. The lights were turned off at 11 p.m. after a five-minute warning flicker.


Mount Zion African Methodist Episcopal Church was built in west Oakland.


Highway 438 (Oakland Avenue) was paved west to the Orange County line and north to the Oakland Bank (now the old Town Hall building).


The town hired two black police officers, R.S. Simmons and R.L. Pollard, to assist officers T. Smallbone and R.L. Smith.

The town ordered 10 lights from Winter Garden Water and Light Company to be placed on posts. The automobile speed limit was set at 10 mph.


The Town Council set the millage at five mills for streets, parks, public areas and lighting on Henschen Avenue and Tubb Street; and five mills for salaries, building and incidentals.

The council voted to build sidewalks in certain areas of town.

A clay road was put down in front of stores leading to the train depot at a cost of .506 cents per cubic yard.


The town added more sidewalks and streetlights.


Oakland had its first motorized school bus, a Model T Ford that replaced the previously used one-mule wagon. Driver Tilly Rosell hauled children from Killarney.


The town dock was built on Lake Apopka at the end of Tubb Street.


A new concrete jail was built.


Florida Telephone Corporation granted the town a 20-year franchise. A rest house was built at the town dock, complete with two flushing toilets.


The town entered into a contract for street paving. Residents petitioned the council to put a stop to camping in the big city park. Later in the year, the town took over Erskine Sadler’s lease on Block 35 to use as a tourist camp. The town annexed all property from Tildenville to Killarney with 41 of the 43 voters in favor of the move. The Oakland Bank closed with all of the town funds. Money was borrowed from First National Bank of Winter Garden to operate on until the next tax collection. In October, the bank reopened, but only 60% of any given account was available.


C. W Olsen, who was given a franchise for furnishing water in 1925, entered an agreement with the town to supply water to the dock, parks, jail, pound and campground for $60 a year.


First National Bank of Winter Garden took over the Oakland Bank, purchasing the building and land for $2,250. The tables and chairs cost an additional $12. Grover C. Tubb was appointed deputy clerk, and later clerk, of the town.


The council voted to spend $1,500 for an American LaFrance Co. fire truck with three chemical tanks mounted in a Model T truck chassis.

The Oakland Chamber of Commerce was allowed to build shuffleboard courts in the big park.

The council cut Clerk Tubb’s salary from $75 to $5; the town had $21.20 in its treasury. The next month, he was rehired at $75 a month. The town opened an account with Bank of Ocoee.


The town leased the Town Hall lobby to Mrs. Rhodes to use as a post office at $100 annually. Eight days later, Winter Garden was paid $25 for responding to an interior fire at Town Hall.


A boys school was opened in the old hotel.

* From 1931-41, the town held few council meetings because, in part, there was no money in the treasury. In some years, the town spent no money, even cutting off the lights in Town Hall and the post office. In 1936 and ’38, the town held one meeting in the spring and one in the fall. In other years, there were only three meetings.


Tubb’s wages were cut to $5 again, and all street work was discontinued.


C.M. “Pete” Tucker was appointed constable.


The town’s property tax ended, perhaps because times were hard and few people could afford to pay, according to records. A volunteer fire force was formed with Tubb as chief, Lundeen as assistant chief and seven council members as firefighters.


Two Army camps were set up on Lake Johns and on the old Oakland golf course, and the troops practiced drilling on Oakland’s main street. Dewey Vick and R.L. Smith were running for the mayor’s seat. Each received 10 votes, the council ruled “no mayor elected” and so the town operated without a mayor.


The town dock was rebuilt.


The town passed a utility tax ordinance.


Dave Starr was appointed city marshal. The big park finally received a name: Speer Park.


Children could roller skate in the new rink built in Speer Park. A flashing stoplight was installed on Highway 438.

Pete Tucker was elected justice of the peace.


The town bought the water works from Olsen. The Tavares and Gulf depot was closed.


Tubb was sworn in as marshal at $25 a month.


The flashing stoplight was sold to the Winter Garden Lions Club for 2/3 its original cost. Albert Walker became mayor.


The T&G depot was torn down.


The town contracted with Florida Power for streetlights. Boney Subdivision was annexed into the town.


A zoning ordinance was passed. The new Town Charter was approved by State Legislature, moving the town limits back to those of 1886.


Town Council meetings were set for the first Tuesday of each month.


The new post office was dedicated.


A contract for $5,048 was signed to pave Tubb Street from Henschen Avenue to the railroad crossing.


A new 1,000-gallon pressure tank was installed in the water system.


Oakland bought the black elementary school property from the Orange County School Board for $5,000.


A full-time police officer was hired for the town. Trinity Baptist Church was dedicated. T&G train service was discontinued. Due to WS. Arrington’s failing health, a new city clerk was hired.


Agnes Smith was made postmaster.


T&G railroad ties and tracks were taken up.


All town streets were given names honoring longtime residents. Streets and avenues were designated by numbers prior to this time. Avenues No. 1-8 became, respectively, Speer, Vick, Briley, Petris, Gulley, Henschen, Oakland, Hull and Sadler. Two previously unnamed avenues on the west side became Postell and Herriott. Streets No. 1-10 became, respectively, Starr, Brock, Arrington, Tubb, Cross, Daniels, Walker, Nixon, Pollard and Jefferson. Two streets in Boney Subdivision were named Smith and Winters, while two avenues bounding the subdivision on the north and south became extensions of Gulley and Henschen.


The Oakland Volunteer Fire Department was authorized. No one qualified to run for mayor, so H.S. Hull Jr., Town Council president, became the acting mayor.


Curtis Massey was elected mayor.

The council voted 3-2 to allow Gallman’s Oakland Inn tavern on the west side of town to sell beer on Sundays.


Was a quiet year in Oakland, Bicentennial of the Country.


The town dedicated the original Grover Tubb Fountain.


Oakland forgot to include the name change from “city” to “town” when it approved a proposed charter revision, so it didn’t appear on the ballot that year. Mayor Sam Hovsepian was quoted as saying he prefers “village.” Oakland was considered a city after a charter revision in 1959.

Head Start center was opened at 525 W Tubb St. with funding from Orange County.

Carol’s Country Store was reopened, once again giving residents a place to buy groceries.

Massive fish kills were recorded in Lake Apopka.


The new town charter was passed that established the makeup of the commission that is used today. Until that time, the mayor served only as a figurehead and could only vote if there was a tie. The commissioners chose a president who had voting power and acted as the head.

The Town Council voted to drop plans for funding a dock and a bike trail in favor of a new fire station.

The council also voted to charge residents $3 monthly for street lighting.


The state threatened to pull Oakland’s charter and resolve the township back into Orange County. There were no taxes at the time, and the annual report to the state showed a deficit in spending. The town did have money, however; it just wasn’t structured properly in the budget.

The town won a county contest for the “biggest, best and most beautiful tree,” which was an 87.5-foot-tall, 400-year-old live oak called the “spider tree” by the residents because of its shape. The tree at Bob Willis’ house won second place in the contest.

The remaining fish camps ceased operation on Lake Apopka.


Oakland had three full-time employees (Town Manager Bernese Fleming and two police officers) and three part-time workers (a clerk and two maintenance workers).

An entire truckload of trash was buried on the corner of Arrington Street and the West Orange Trail because the truck wouldn’t start, it was the middle of summer and the garbage was smoking and smelling.


The last Atlantic Coast Line train went through town.


Fire Chief Jim Briggs resigned, stating a lack of professionalism and leadership as the reason.

The town budget was $216,000 (in the General Fund) and $65,000 (for the Water Department).

The Oakleaf was published by the town as a monthly paper.


The Friends of Lake Apopka organized in an effort to save the polluted lake.


Oakland, with Jake Voss as mayor, enacted the town’s first property tax in 60 years. The millage rate was set at 4 mills, which was expected to generate approximately $100,000.


Orange County Chairman Linda Chapin cut the ribbon to signify the opening of the West Orange Trail through Oakland.


The Oakland Gazette newsletter was started, and 22 issues were published at a subscription rate of $10 per year. Volunteer town residents did all the work.

The town gave approval for Oakland Pointe, the first of several subdivisions to be built in the town. (Future subdivisions would include Trailside, John’s Cove, John’s Landing, Winter’s Landing and Oakland Estates.)

The Florida Legislature passed the Lake Apopka Restoration Act and allocated funding to begin the buyout of the north-shore muck farms.


The police department started a K-9 program. In what would later be considered the first round of shakeups in the town, the commission fired Town Manager Bernese Fleming for “numerous instances of improper acts and insufficient management” and terminated Town Auditor Kevin Munroe for preparing the town audit with a suspended license and having another licensed accountant sign the audit without the commission’s prior knowledge. A day after Fleming’s suspension, town bookkeeper Joyce Williford resigned. Later that year, in an effort to operate in the black again, the town closed its building department and terminated Police Capt. Robert Cockcroft and Code Enforcement Officer Jack Jordan.

Harold Emrich was hired as Town Manager.


The Oak Tubb Bed and Breakfast opened.

The Town Commission enacted the Gateway Corridor Ordinance that would strictly control the types of businesses and their architectural styles, landscaping, signage and lighting along Highway 50 and Oakland Avenue.

The Oakland Nature Preserve was purchased with funds from the Florida Communities Trust, and an agreement was made with the town and the ONP board of directors that the board would develop and manage the preserve.

A massive bird kill was recorded near the Lake Apopka muck farms.

Oakland’s controversial old “blue building” - B.N. Gulley’s hardware store until 1948 and in recent years a real eyesore - was torn down.


Oakland hired its first female police officers, Nicole Torres and Dawn Beninato.

A committee unveiled plans for a possible town center. Homes In Partnership and the town dedicated five homes.

The Amon Pavilion was constructed at the Oakland Nature Preserve.

Jay Evans was hired as Town Manager.


There was an outcry from residents when the Town Commission discussed placing paving options on the election ballot.


A town center design was unveiled.

Oakland received Tree City USA designation.

Police Chief Tim Driscoll disbanded the K-9 program, saying that although it’s a great program, it wasn’t working for Oakland.

ONP dedicated its boardwalk that leads to Lake Apopka.

Friends of Lake Apopka (FOLA) completed its development of design guidelines for future development in the Lake Apopka Basin.


After years of planning, the town dedicated West Orange Charter Elementary School (now called Oakland Avenue Charter School) and the police and fire facility.

FOLA completed its design of the Greenways and Trails project, which includes a loop trail around the lake.


The town held a dedication ceremony for the new Oakland Town Hall and adjacent meeting hall, the round-about and the fountain on Tubb Street.

The Honor Forest was dedicated at the Oakland Nature Preserve.

The town and ONP joined resources to organize the Oakland Heritage Festival to celebrate their “natural and cultural heritage.”

Oakland survives the year of four hurricanes hitting Central Florida.


Oakland Avenue (CR 438) was designated as part of the Green Mountain Scenic Byway.

Town Manager Maureen Rischitelli is hired in January. The Town has 24 employees.

The renovations to the Historic Town Hall are complete.

The Management and Discussion Analysis is completed as part of the financial requirements of GASB 34. Town budget for FY05-FY-06 is adopted and contains $2,463,461 for general government and $784,780 for utility. Millage rate remains at 4.9245, which has been constant since 2001.

K.C. Cunningham retired from our post office and Dean Monsold appointed postmaster.

Winter’s Landing subdivision breaks ground.

Town Commission approves the Town’s first Planned Unit Development in Oakland Park.

Town works on its elements of the Wichita Study and is continuing to develop its Water Conservation Program.

Oakland receives no damage from the late October Hurricane Wilma, which this storm season saw more Category 5 hurricanes and broke the record for most named storms.


Oakland Avenue Charter School Operations are resumed by the Town and the School receives an “A” grade.

Winter’s Landing completes its build out.

The Town addresses concerns with development in Lake County Plaza Colina and the impacts of road traffic.

The Town meets with Department of Transportation and the Turnpike Authority to raise concerns about the impacts of the State Road 50 widening and Turnpike expansion.


Healthy West Orange Arts and Heritage Center constructed.