AS OF MAY 2009, SPONSORSHIP OF THIS TRAIL HAS CHANGED. PLEASE DIRECT ANY QUESTIONS OR COMMENTS ABOUT IT TO TROOP 145 BSA, c/o TOM DAVIS, SCOUTMASTER, 3233 AVALON ROAD, WINTER GARDEN, FL 34787, [email protected], http://bsatroop145.com.
WARNING - This trail may pass through one or more neighborhoods which, although full of history, may now be unsafe for individuals on foot, or which may make you feel unsafe there. Hikers have been approached by individuals who have asked for handouts or who have inquired (not always in a friendly manner) why the hikers are in their neighborhood. Drugs and other inappropriate items have been found by hikers in some neighborhoods. It is suggested that you drive the hike routes first to see if you will feel comfortable walking them and, if you don't think it's a good place for you walk, you might want to consider (1) traveling with a large group, (2) doing the route on bicycles, or (3) choosing another hike route. The degree of comfort will vary with the individual and with the time and season of the hike, so you need to make the determination using your best judgment. If you hike the trail, you accept all risks involved.
This is the western end of Phase I of the West Orange Trail, ending about 5.2 miles to the east in Winter Garden. It is part of the national Rails to Trails movement, converting to recreational use land which once was under railroad ties and rails.
In 1880, a few immigrants from County Kerry, Ireland, established a settlement here and named it Killarney. Although most returned to Ireland following the freezes of 1894 and 1895, some remained.
The first Killarney post office opened on October 7, 1899, with Belle Walton Burdett as the postmaster. It was discontinued on May 31, 1902.
At the intersection here of the tracks of the Seaboard Coast Line and the Tavares & Gulf Railroad, a sawmill office was built in about 1908. James William Jones acquired it and operated a general store in it. When the post office was reestablished on May 18, 1926, it was located in the back of Jones' store, and there it remained until 1968.
A portion of the store's foundation is still visisble north of CR 438.
The Killarney post office was located in this small frame building from October 1, 1968, to 2000.
Buried here are Oakland's black citizens, including "Uncle Bob" Pollard, after whom Pollard Ave. is named.
This is reputed to be the oldest remaining house in Oakland. It began as a wayside inn built in the 1860s by an English couple, who later returned to England. Capt. Bluford G. Sims taught grades 1-8 here five months a year.
It was later remodeled as a residence and in 1903 became the home of Ezekiel C. Vick and his family. It later was the home of Mr. Vick's daughter, Dewey, and her husband, E. Lee Mathews.
The first Baptist church building was erected in the 1880s near the Tavares & Gulf railroad track. After it was destroyed, the Baptists held monthly services in the Presbyterian church building.
The present church was organized in 1947 as the Oakland First Baptist Church and acquired a small building two blocks west of the post office and near the railroad tracks, just back of the old ACL railroad depot site. That prior building was used until 1980, when the church became a mission of the College Park Baptist Church.
In 1983, it reorganized as West Orange Baptist Church. The present building was designed by Bob Macchi, Buddy Phillips and Frank Morrow, and was built in late 1983. The church is the home of the Central Florida Christian Bass Club.
As you walk through the cemetery, you will see the burial plots of the white families that figured in the establishment and growth of Oakland. Some of them are:
Sadler (on your left)
James Hardy Sadler (1859-1934) of Abbevile, South Carolina, arrived here as a young boy to live with his grandfather, Judge Speer. He homesteaded 160 acres on Black Lake Rd. and planted oranges and vegetables. He married Matilda Minerva Tilden (1868-1921).
Tilden (on your left)
Luther Fuller Tilden (1834-1929) and his wife, Emily Willis (1840-1925), moved from Illinois and arrived in Florida in 1876. After living in Apopka for a time, they came here and planted tomatoes, helped establish the first schools and the Beulah church. Mr. Tilden was instrumental in helping others rebuild their lives after the devastating freezes of 1894-95.
Gulley (on your left)
Richard Lindsay Gulley (1877-1948) of Anderson, South Carolina, came to Oakland in 1895. He came to work with the railroad, but stayed to be a farmer. In 1900, he married Nona Dunnaway (1883-1972).
Connell (on your left)
George Frank Connell (1856-1908) came with his wife Lulu (1864-1950) from Staunton, Virginia, and with his brother owned groves and a farm.
Brock (on your left)
James Orlando Brock (1856-1929) arrived from Toccoa, Georgia, in 1888. He married Sarah Judith Perkins (1859-1951). The Brock family was involved in the grocery business in Oakland for over 25 years.
Speer (on your left)
A Speer cemetery was located on the homesite of James Gamble Speer (1820-1893) on Killarney Rd., which was occupied by his son, Arthur Speer (1852-1940), who had married Alice Roper in 1877. After she died in 1880, Arthur married Martha C. Kincaid (1846-1928) and after they both died, the property was sold. The new owner destroyed the cemetery and piled the tombstones in a corner of a field. Some of the stones were retrieved and relocated here, including the one bearing the names of James Jackson and Sansparilla Dewsinberry, in the row running south of the concrete slab adjacent to the dirt road.
Petris (on your left)
Edmund E. Petris (1848-1931) and his wife, Louise I. Molner (1853-1918), came to Florida from New York City in 1874. Mr. Petris operated a general merchandise store in Sanford, then moved here and upholstered Pullman car seats for the railroad.
Smith (on your right)
Charles Frederic Mather-Smith (1863-1941) and his wife, Grace Smith (1884-1962) were interred in elaborate mauseleums on their estate overlooking Lake Apopka. After vandalism problems there, they were moved here to the cemetery.
Hull (on your right at the end of loop)
Simeon Benjamin Hull (1867-1945) came to Oakland in 1905 and married Marguerite Matilda Winkelman (1876-1968). Mr. Hull helped to plant the Tilden groves, and owned groves of his own.
Charles Frederic Mather-Smith and his wife, Grace Smith, had been members of the Country Club, but desired more golf. They built the West Orange Country Club here near Johns Lake, and surrounded it with an 18-hole golf course. During its existence, the club was a popular place for parties, dinners, masquerades, golf tournaments and buffets. It later closed, and was subsequently reestablished at another location. All that remains is a large block and brick entry arch which used to welcome visitors to the Country Club.
Although the single community of Tildenville grew out of a single 561-acre tract purchased by Luther Fuller Tilden in 1878, its being bisected by SR 50 has caused it to evolve into two separate communities. Notice the differences between this neighborhod and the rest of Tildenville which will be visited shortly.
This portion of Tildenville has as one of its social centers the Tildenville Missionary Baptist Church, organized in 1939 by Rev. I.J. Johnson.
Luther Willis Tilden (1869-1941) and his wife, Virginia May Wise, had nine children. He had come to Oakland at the age of five, and received his early schooling in a shack along this road, just south of SR 50.
Behind the home is Lake Brim, the south shore of which was the site of a sawmill owned and operated by Col. Isaac Huston of Louisiana. When he saw Lake Apopka, he bought a big block of land on the south shore and brought in slaves to clear it.
Luther Fuller Tilden (1834-1929) moved to Apopka in 1875, upon the advice of the doctor treating his bronchitis. He built the first house in Apopka with glass windows. In November of 1877, he relocated to the south shore of Lake Apopka, where he bought 561 acres from the Ropers. The village he founded is now called Tildenville.
Tilden built this large two-story home near the lake with hand-sawed pine lumber. The trees grew on his Apopka farm, and the lumber was rafted across the lake.
His brother-in-law, James Willis, arrived in 1877 and homesteaded on an adjoining 160 acres. He built his two-story home on what is now Tildenville Rd. (CR 438).
Here is located the headquarters of the Association, which in 1909 began using the citrus brand labels "Fellowship" and "South Lake".
A school was built in 1905-06 on this land donated by Confederate veteran James Willis (1835-1916). When it was damaged by a 1928 tornado, a new brick school building was erected across the street and to the right. A later Tildenville Elementary School was built in 1964 on the site of the 1905-06 school.
This house was built in 1919 for the Hall family.
George Frank Connell and Lulu G. Connell built a home here. Mr. Connell's claim to fame was that he was the owner of the first automobile in Oakland, a one-cylinder Cadillac.
It was later the home of Mr. and Mrs. Clarence H. Tilden, which was lush with tropical plants. It was a mecca for horticulturalists and garden lovers. J.S. Reddick bought it, tore it down, and built a large home in its place.
On this land was located the home of James E. Willis (1835-1916) and his wife, Elvira Hobart (1844-1912). The home was removed in the late 1950s and replaced with these two new homes for his grandchildren, Robert Cooley Willis (15200 CR 438) and Helen Willis Bourland (15150 CR 438).
This was the home of James Hardy Sadler, who planted the row of large oak trees dividing the road.
Sadler (1859-1934) was a grandson of Judge Speer. His 1906 home was the showplace of Oakland. Later it was divided into two houses, which are now located behind the present home. Sadler was a promoter of the Bank of Oakland, which opened in 1912, and he served as president until it closed in 1926. The bank reopened in 1927, and was taken over the following year by the First National Bank at Winter Garden.
When the bank closing threatened to cause depositors to lose money, Sadler paid them out of his own pocket.
This was the home built in 1910 by Charles Herbert Tilden, and was later owned by his granddaughter, Margaret McKinnon. The dining room is paneled with pine sheets used by Tilden for the manufacture of orange crates.
Daniel McKinnon IV (1872-1933) and his brother, William, came from Maxton, North Carolina, in 1905. Daniel married Mable Tilden (1884-1963), and Will married Blanche Wise (1883-1952). Daniel's interests included citrus, lumber, and naval stores.
The first Presbyterian church in the area was founded by Judge James Gamble Speer, who secured occasional preaching services by the pastor from Apopka. Early services were held in a log schoolhouse in Beulah at the Reeves settlement, and later in Speer's home and Eliot S. Dann's home.
A new church was organized by seven members in 1887, and a church building had been constructed in anticipation of its founding. A new church building, of cream-colored brick, was built in 1919 on a lot donated by Luther Fuller Tilden, a Methodist.
The 1887 building was given to the Methodist congregation in 1923. After poor attendance closed it, it was demolished. The remaining members of that congregation either joined the Presbyterian church or became affiliated with the Methodist church in Winter Garden.
The education building on the east side of the church was dedicated on March 27, 1950. The present sanctuary was dedicated on May 30, 1971, and it contains the original 1887 pulpit. The stained glass windows were made locally by Nobis Studios. The memorial window at the entrance lobby is dedicated to the memory of Judge Speer. Another window near the church offices honors Luther F. and Emily A. Tilden.
Next door to the 1919 brick Presbyterian church had stood a two-story school, which had been built in 1890-91 on land donated by Judge Speer. It was later bought by Mr. Crenshaw and converted to a house, and later was used as a manse for this church.
Originally, Peter Demens lived at this site. Mr. and Mrs. Robert Fulton Smith (1834-1907) came with Demens to work for the railroad. Mr. Smith was a railroad engineer, and bought Demens' house when the latter moved to North Carolina. Mr. Smith operated a blacksmith shop behind the house.
A granddaughter, Annie Doris Smith, married Dave Starr, who was the Orange County sheriff for 23 years. They tore down Demens' house in about 1971 and replaced it with the present ranch style home.
This was the 1879 home of Edmund E. Petris (1848-1931). He had arrived in Mellonville in 1874, then ran a general merchandise store in Longwood. When the railroad was run to Oakland, he moved here to this spacious company house and worked as an upholsterer of Pullman car seats. He served as the station agent for 35 years and was one of the community's most popular citizens.
When Simeon Benjamin Hull and his wife, Marguerite Matilda Winkelman, moved to Oakland about 1905, they lived for a while in this house. Mrs. Hull taught school at Glenn Ethel (near Sanford) and Conway, then became a nurse and served abroad during the Spanish-American War. The Hulls met while she was working as a nurse at the Church and Home Hospital in Orlando.
The Tavares, Apopka and Gulf Railroad (T,A&G or T&G) desired to extend its line from the northwest through Oakland around 1890. The Orange Belt Railroad threatened to obtain an injunction preventing it from doing so, if T&G came too close. In response, the T&G workmen built the line in a more easterly direction, apparently missing Oakland.
When a Sunday and holiday occurred consecutively, so that the courthouse would not be open, they switched the tracks south and reached Oakland before Orange Belt representatives could get their injunction. T&G built their depot at this location. The line was eventually taken over by Seaboard, then discontinued, and most of its tracks in Oakland were removed.
Peter Demens from St. Petersburg, Russia, purchased a railroad franchise originally issued to Arnold, Miller & Hall to construct a railroad line from Lake Monroe to Lake Apopka. He also acquired one to continue the line to the Tampa Bay area. His original route was planned to pass two miles south of present-day Oakland, but Judge Speer persuaded Demens to bend his route to include this community.
In exchange for the rerouting, Speer contributed to Demens' company Speer's half interest in 180 acres for a townsite, 15 acres for a depot and railroad shops (to be moved from Longwood), and five acres for a public park.
On December 1, 1886, Hamilton Disston, then the largest individual landowner in the United States, visited Demens' office and offered the railroad one-fourth of all his land within six miles of the proposed route to Pinellas Point. Demens received about 60,000 acres, enabling him to make the completion of his dream possible.
However, Demens was heavily in debt, a large portion of which resulted from the purchase of steel rails on credit from the George W. Stetson Company. The business was saved by a loan from the New York meat business H.O. Armour & Company. In 1887, the railroad pushed toward the southwest but was stopped when the money ran out and the engines were chained to the tracks.
A $10,000 temporary loan removed the chains, but an angry mob of 100 men on October 1, 1887, brought a new threat. They demanded their wages and threatened to lynch Demens, but were pacified when Demens' Oakland friends pitched in enough money to meet the payroll.
In April of 1888, the last section of roadbed was graded into Pinellas Point. Demens was able to convince the local residents to change the community's name, something he couldn't do in Oakland, and the village of St. Petersburg was born.
In October of 1860, Judge Speer obtained a post office for the community, with William Roper as the postmaster operating out of a cabin which he built. Mail left Orlando by mule at noon on Monday, reaching Starke Lake, Oakland and Montverde, where the postman spent the night. On Tuesday, he reached West Apopka, Yalaha, Bloomfield and Okahumpka. The return trip was made on Thursday and Friday.
The post office was discontinued on March 29, 1867. After the horseback carrier stoped, Speer brought the mail by boat from Apopka. The post office was reestablished on July 22, 1877, with Speer as postmaster.
A small post office building was erected shortly after 1900 just south of the railroad track, facing Grace Park and the depot.
Charles Federic Mather-Smith (1863-1941), a retired Chicago paper manufacturer, and his wife, Grace Smith (1884-1962), sponsored a landscaped park here, between the railroad depot and the post office, and named it Grace Park. They paid the cost of installing a fountain, benches, trellises, flowering vines and shrubbery. The park was fenced to keep animals out.
They also built a 22-room house overlooking Lake Apopka, which became the social center of the area. The house was torn down for its lumber shortly after Mr. Smith's death in 1941.
Mrs. Smith lived for a while in a guest house on the estate, and moved away to marry a Mr. McAlpine. She returned to the guest house after the marriage was dissolved.
Oakland was incorporated as a town on November 1, 1887. Oakland's greatest era was from 1885 to 1890, but in 1890, a major fire completely destroyed the business district. Oakland settled back to its agricultural resources, which were severly damaged by the 1894 and 1895 freezes. By 1900, the population had dropped to about 200.
The center of Oakland's government sits here, in what originally was the Bank of Oakland building. It was built in 1912, and J.H. Sadler served as the bank's first president. It closed in 1926, reopened briefly in1928, and closed permanently that same year. The town bought the building in 1928 for $2,250. From 1930 to 1964 the front portion served as the post office. The police department remained here until 1984.
Oakland was granted a charter as a city on June 1, 1959.
Peter Demens' roots showed through at the depot, built with a Russian architectural style, to the west of where the small white building presently sits on the north side of the West Orange Trail.
After the arrival of the railroad, the town began to boom. Buildings went up for a hotel, an opera house, stores, a hospital, many small workmen's homes, a telegraph office, a newspaper, and substantial homes for company officials.
In 1889, Oakland became the junction of the Orange Belt and the Florida Midland Railroads. Not long after that, Peter Demens moved to Asheville, North Carolina. In 1892, he went to Los Angeles and acquired a steam laundry.
Demens also grew citrus, wrote for the Los Angeles Times, worked as an Associated Press reporter, and took charge of the Russian government purchasing bureau until that country was overthrown by the Bolshevists. Demens died on January 21, 1919.
Severe freezes on December 26, 1894, and February 7, 1895, nearly eliminated the freight traffic on the Orange Belt. On March 31, 1895, the line was leased to Henry B. Plant and was operated as a part of the Plant System. In July of 1902, the Plant System was merged into the Atlantic Coast Line Railroad Company, which merged with the Seaboard Air Line in July of 1967 to become the Seaboard Coast Line Railroad Company.
A two-story wooden building housing the stores of Michael (east half) and Brock (west half) was built here by J.O. Robinson after the fire of 1912. It was torn down in about 2001.
J.O. Brock owned an old cow that was allowed to roam the neighborhood, and which ignored boundaries and barricades. It was especially fond of the prize grapefruit tree behind the white picket fence in Mr. Michael's yard. During the last of many episodes in chich the cow jumped the fence to eat the tender grapefruit leaves, Michael fired his shotgun to scare the animal out of his yard.
The animal bolted as intended, but ran headfirst into a barn door and died from the impact. Michael approached Brock and asked him how much he would charge to sell his cow. Brock thought about it and set the price at $20. Michael pulled $20 bill out of his wallet, handed it to Brock, and said "Here's your money - I just killed your cow.)
The jail located here housed an occasional drunk, often George Bowen. He lived in a small cottage near Tildenville, and sometimes received a bottle of a potent beverage from callous youths just so they could see him put on a roaring drunk.
In the early railroad days, this was the action center of Oakland. A wooden frame grocery store stood where the later Michael/Brock building now is. Next on the west were office buildings, then a hotel. On the west end of this area was the Union Club. Also known as the Opera House, it was built in 1886, and was destroyed in the 1890 fire along with most of this business district.
James Orlando Brock (1856-1929) had a grocery business in Oakland for over 25 years. This home was built as a boarding house by the railroad in 1886, and was owned by the Brock family from 1905 until 1977.
The hotel was completed in 1910, and rooms let at $3.00 per day. It was attached to a home built in 1890, and used by the hotel as a dining room. The hotel was condemned and torn down in the 1920s, and the dining room was converted back to a residence. This home is the old dining room, and the vacant lot north of the house is where the hotel was. It was also known as the Wingate House, and originally was a Tilden property.
St. Andrews Episcopal Church was organized by 1895, with services first held in a home and later in the Presbyterian Church building. In 1904, a house was acquired and moved across the street from here, and was converted into a quaint chapel building.
By 1922, the church no longer existed. Charles F. Mather-Smith acquired the site and had the chapel torn down. Some of the chapel's windows were moved to a house on Fourth St.
The house of John Charles Michael (1864-1954), because of its visible location, was an aid to fishermen on the lake. In a cupola, lanterns were hung to guide them at night. Across the street was the home of his brother, Stephen Michael.
On a wooded slope on the south shore of this lake, wealthy settlers from South Carolina established Oakland Park in 1844. They and about 100 slaves cleared land for cotton, corn and sugar cane, and by 1860 it was a busy industrial center with noisy sawmills, a grist mill, sugar mills and cotton gins. The rich mucklands were good for farming.
Not long after the Civil War, Oakland was dominated by seven main families - the Speers, Sadlers, Tildens, Wises, Willises, Petrises and Hulls.
In November of 1877, Judge Speer and others living near the lake petitioned the Internal Improvement Fund for ownership of the swamps and overflowed lands north of the lake. Their request was granted in 1879, contingent on their draining the lake and digging a canal to connect it to Lake Dora.
The Apopka Canal Company began immediately and completed the canal in 1887. That project allowed oranges to be loaded on a boat at the Oakland dock and be shipped solely by water through lakes and the St. Johns River to Jacksonville and Savannah.
Zellwood Florida Farms applied for and obtained permission to lower the level of Lake Apopka to develop the Zellwood mucklands. In May of 1915, 135 truck farmers met at Tildenville to try to halt the project. Orlando attorney Leroy B. Giles worked with L.W. Tilden in getting legislation adopted which prohibited a private party from lowering the level of any body of water of more than 2 square miles, without the written consent of all property owners abutting it. However, it was determined not to affect the Lake Apopka project, since the proposed lowering would not bring the level below the "low water mark" of 62 feet.
Judge James Gamble Speer, born in 1820, moved from South Carolina to Fort Reid and Fort Gatlin in 1854, and was appointed a member of the Indian Removal Commission. He moved to this area that same year and began a farm. At the time, there were six Indian villages nearby.
Following the Civil War, Speer sold his Oakland property to Dr. Buford, who in turn sold to James Jackson. Years later, Speer bought his land back from the Jackson estate. He added to his holdings during the late 1860s, and owned from Lake Apopka to John's Lake, including most of present-day Oakland. He built a small home and a boat, and ferried vegetables across the lake to trade in Apopka.
Later, he built a larger home on a hill overlooking John's Lake, subsequently destroyed by fire. Judge Speer died in 1893. This park was named in his honor. Shortly after the turn of the century, the town installed two tennis courts here.
This home was built in about 1922, facing Speer Park. It is also known as The Draper House.
This congregation is one of the oldest in Orange County, having been established in about 1844. The sanctuary here was rebuilt and dedicated on April 21, 1991.
The original church building was erected in 1911 under the supervision of Rev. J.R. Bronson, and rebuilt and rededicated on November 30, 1919, while Rev. R.D. Nimmons was the pastor. It was substantially renovated in 1944, and rebuilt in 1990.
The present sanctuary for this congregation was dedicated on June 8, 1969, with Rev. H.P. James as pastor.
This granite marker commemorates the family of S.B. Hull, who arrived in this area in about 1905. This is one of the oldest orange groves in the state, known as the Burdette Island Grove before the Hulls bought it in 1912. Simeon Benjamin Hull served as a trustee of the Oakland-Winter Garden School District, second vice president of the Orange County Chamber of Commerce, and was appointed by the Orange County Board of Commissioners to make the 1927 Agricultural and Industrial Survey for Orange County for the State Department of Agriculture.
Early Settlers of Orange County, Florida, by C.E. Howard (1915)
Flashbacks: The Story of Central Florida's Past, by Jim Robison and Mark Andrews (The Orlando Sentinel 1995)
Full Steam Ahead!, by Albert Parry (Great Outdoors Publishing Company 1987)
History of Apopka and Northwest Orange County, Florida, by Jerrell H. Shofner (Rose Printing Company, Inc. 1982)
The History of Public Education in Orange County, Florida, by Diane Taylor (Orange County Retired Educators Association 1990)
Oakland: The Early Years, by Eve Bacon (The Mickler House 1974)
Pictorial History of Florida, by Richard J. Bowe (1970)
Click here for a copy of the trail rules.