Instructions:
1....Print this file.
2....At its end, click on "rules" to see a copy of the trail rules, print it, and then click where indicated at the end of the 3-page rules and patch order form to get back to the list of Florida trails.
3....If you want a hand-drawn map showing the locations of all of the sites, send a self-addressed stamped envelope to Steve Rajtar, 1614 Bimini Dr., Orlando, FL 32806.
4....Hike the trail and order whatever patches you like (optional).
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.
The fort was built near here in 1835 by soldiers commanded by Lt. Col. Alexander C.W. Fanning (1788-1846), along the military road from Ft. Mellon (Sanford) to Ft. Gatlin (Orlando). The fort was named in 1838 in honor of William Seton Maitland (1798-1837) of New York. At the same time, the name of Lake Fumecheliga, Seminole for "muskmelon place", was changed to Lake Maitland.
Andrew Jackson had commissioned William Maitland as Brevet Captain for his gallantry and good conduct at the Battle of Withlacoochee on December 31, 1835, and the Battle of Welika in July of 1836. He was severely wounded at Wahoo Swamp on November 21, 1836, and spent nine months trying to recover from his wounds. Despondent over his condition and humiliated over his having to leave his men and the fighting, he jumped overboard in Savannah Harbor and drowned in November of 1837.
The fort was never used in battle, and was abandoned in 1842. The following year, the first homesteaders arrived.
Architect and carpenter William S. Waterhouse built a home here in about 1885 for Charles H. Hall of Marquette, Michigan, who had bought the land in 1874. The Hall home was sold in the 1930s to Chester Fosgate, who sold it to Ed Owens.
In 1948, Mr. and Mrs. Edgar Smart bought it and lived here until 1959, when they sold it to a developer. It remained vacant for several years, and was torn down. In 1972, the West Cove Condominiums were built.
On March 15, 1935, a group of Seminole Indians unveiled a coquina rock marker with an embedded D.A.R. plaque, on land donated by Edward R. Hall, son of Charles, here at the site of the fort. It is dedicated to Capt. Maitland, "Hero of the Seminole Indian War."
This Frame Vernacular style building was erected in about 1915 as a private residence. It now houses the Enzian Theater, which shows foreign and limited-run movies.
"Frame Vernacular" is the most common style of residential architecture in Florida. It is a common wood frame technique employed by lay or self-taught builders. They are typically one or two stories in height, are usually rectangular, and construction is generally of pine on masonry piers of brick. Horizontal siding or shingles cover the exterior walls, and the original wood shingles or pressed metal roofing is often later replaced by composition shingles.
Built originally as a single-family home, this building has now become a part of the Park-Maitland School. It was constructed as a Bungalow in about 1920.
This Frame Vernacular style home was built in about 1925. Homes of this style generally have front roof peaks, making the height of the front taller than its width. Windows are usually double-hung sash. Decoration is typically limited to ornamental woodwork such as turned porch columns and balustrades, patterned shingles, knee braces, and exposed rafter ends under the eaves.
This Bungalow was built in about 1925.
In 1875, Judge Lewis H. Lawrence, a millionaire boot and shoe manufacturer from Utica, New York, moved to Maitland. On a 10-acre tract of oranges and vegetables on the south shore of Lake Maitland, he had this house built in 1882.
Lawrence sent the first telegraph message from Winter Park on January 1, 1883, to his friend, President Chester A. Arthur. It read, "Happy New Year. First message from office opened here today. No North. No South." In April of that year, Arthur paid him a visit here, and said that "Winter Park is a charming village, the prettiest town of all."
The front has a simple Federal style entrance, with a dual grouping of porch columns. The heart of cypress siding on the front is original.
Henry S. and Annie Chubb bought the property in 1889, when they came to Winter Park to lay out a grove for Col. Franklin Fairbanks. Mr. Chubb was active in Republican politics, helped to found Eatonville, and served as mayor of Winter Park. His purchase of 22 acres from Capt. Josiah Eaton provided the initial land for the Town of Eatonville.
This Mediterranean Revival style home was built in about 1926. In Florida, this style is generally more prevalent in 1920s land boom subdivisions. The style utilizes architectural elements associated with Spanish or Mediterranean roots such as flat or hip roofs covered with ceramic tile, stuccoed exteriors, and arched entrance porches supported by square columns.
This Bungalow was built in about 1926. "Bungalow" is derived from a Bengali word meaning a low house with porches, used as a wayside shelter for nineteenth century British travelers in India. Between 1910 and 1930, the bungalow was one of the most popular home designs in Florida.
A bungalow is generally one to one-and-a-half stories with a shallow pitch roof, with at least two rooms along the front of the house. The masonry piers holding up the porch floor often continue above it, topped by short wood columns supporting the roof. The front door was off-center, and the window pattern was usually asymmetrical.
This and the next three homes (1626, 1616 and 1606 Ridgewood Ave.) were built in about 1926, and are classified as Frame Vernacular. The one at 1626 Ridgewood Ave. appears to have a later second story addition which obscures its original design.
Most of this portion of Maitland was developed during the Land Boom, and construction of many of the surviving homes was in about 1926. This is one, a Bungalow, as is the one across the street at 251 Orange Pl.
Built in about 1926, this home is classified as Frame Vernacular. So are the ones at 227 and 170 Orange Pl., built at about the same time.
This Frame Vernacular house is slightly newer than its neighbors, having been built in about 1930. That year's census showed Maitland with a population of 500.
This Bungalow was built in about 1926 as a private residence. It for a time was occupied by a plant store named The Garden Cottage, and then was an annex of Park-Maitland School.
This Frame Vernacular home was built in about 1926 as a private residence.
In 1919, this home was built in the Frame Vernacular style. It is now a private school.
This portion of US 17-92 was formerly named Vanderpool Ave., after Isaac Vanderpool. In 1876 he, along with H.S. Kedney and the Packwood brothers, laid out the town's streets. Vanderpool also opened the town's first citrus packing house.
Rev. Benjamin Henry B. Whipple of Minnesota, the first bishop in Montna, came to Maitland in 1879. In Florida, Rev. Whipple bought land in 1877 on Lawrence Ave. (now Lake Ave.) and built a home in 1885 directly across the street from here (the present site of Maitland Shores Apartments). He called it "Casa Mia", and he lived there until his death in 1901.
He formed the Church of the Good Shepherd in memory of his son, and began to build the sanctuary in 1883 on land given by James Wilcox and Charles Hall.
The original building followed the Gothic Revival style. A larger sanctuary made from Honduras mahogany was erected here in 1967, just to the east of the original chapel, which is still in use.
See the exquisite stained glass windows on the west wall of the chapel. The third from the left, as viewed from the interior, is dedicated to Josiah C. Eaton, one of the creators of Eatonville. The window includes an anchor and flag, as Capt. Eaton had served in the navy.
Christopher Beasley bought 159 acres here in 1874 for $1.25 per acre. A portion was sold to James Wilcox of Philadelphia in 1880, who sold it to the Episcopal Diocese of Florida later that same year. This home was built in 1892 as the parsonage and was owned by the Diocese until 1941. It was bought in 1955 by Mr. and Mrs. James Arch, who remodeled and enlarged it, and made it their home.
This Bungalow was built in about 1916.
The first Catholic church in Maitland was built here, fronting along Lake Eulalia, in 1881. It sat 100 and Fr. Michael McFaul served as pastor. The church closed in October on 1887. The building was sold in 1919 to Anna B. Tract, who reconstructed it into a house, which was later removed.
This home was built in 1885 as the winter home of Minneapolis businessmen Cyrus B. Thurston. In 1913, it was purchased by Anna E. Hirsch, whose husband was the mayor of Glencoe, Illinois. Mrs. Hirsch developed it into a beautiful estate which she named "Glencoe Groves". It was later owned by their daughter, Verna H. Goodwin, who sold it in 1941 to Clarence Cubbedge, mayor of Maitland. By this time, the original 180 acre estate had been reduced to 13 acres.
In 1949, it was purchased by Arthur O'Heir. Some of the furniture used by the O'Heirs can now be found on display in the parlor of the Waterhouse Residence Museum on Lake Lily.
It is built in the Queen Anne style, and has a fireplace in every one of the eleven rooms. It is now operated as a bed and breakfast establishment.
A group of Union army veterans established a colony at the site of the fort, and desired to incorporate a town. Lacking the minimum of 30 adult men required to conduct such an election, they encouraged blacks to register. The blacks did, and voted in favor of incorporation, making Lake Maitland a city on July 17, 1885. "Lake" was dropped from its name on May 9, 1901, but the charter officially making that change was not adopted until 1959.
However, there was another result of the soldiers' encouraging the blacks to vote. They elected Mayor Tony Taylor and Town Marshall Joe Clark, both black, to the dismay of the white minority. They found this unacceptable, and helped the blacks acquire their own land west of this spot and incorporated their own town, known as Eatonville.
The Florida Audubon Society was founded on March 2, 1900, by Mr. and Mrs. Louis F. Dommerich, and was incorporated on June 27, 1902. Its first president was Bishop Henry B. Whipple, called "Straight Tongue" by the Sioux, a result of his successful treaty negotiations which helped open Montana to white settlement in 1876.
Meetings of the Society in its early years were held at "Hiawatha", the Dommerich home on Lake Minnehaha.
The Audubon Center, which opened in October of 1979, is dedicated to the rescue, treatment and rehabilitation of injured raptors. Hundreds of eagles, owls, hawks and other raptors are returned to the wild each year.
Looking to the southwest, you can see a broad open area on the southern shore of the lake. In 1930, Roy Kyle had an airplane landing strip here.
This home follows the Neoclassical style, and was built in 1936. Homes built in this style generally feature a symmetrical front, hip roof, end porch, a simple frieze band and Doric columns.
A home was built here in about 1910, and was classified as Frame Vernacular in style. It was torn down and the home which replaced it in 2003 appears to follow its prior design.
This Tudor Revival house was built in 1925. Typical features of the Tudor Revival style are steeply-pitched roofs, side gables, interesecting extensions, half-timbering with stucco, and massive end-exterior chimneys.
This land was bought in 1886 by sisters Caroline Chadburne, Mary Chadburne Boynton, and Elizabeth Chadburne Webb, from Medford, Massachusetts. Mary's husband, Eleazer Boynton, built this Frame Vernacular home in 1890.
Eleazer died in 1901, and the home was occupied for a time by his son, E.P. Boynton. The three sisters sold the property in 1920 to Dr. Kenneth E. Kilbourne and his wife, Maud, from Detroit. Beginning in 1933, Kilbourne leased the house to novelists Winston Churchill and Robert Herrick. Churchill was frequently visited by the ladies of Winter Park and Maitland, and kept a ladder outside his second-story bedroom window to escape meeting with uninvited visitors.
The home was bought in 1936 by Mrs. Anna H. Stevens of Chicago, who made considerable alterations and renamed it "High Oaks". She spent her winters here until 1942, when the home was sold to Ralph and Earnestine Day of Bridgeport, Connecticut.
This home with the name of "Glen Coe" on the entry gate was built in about 1935, and follows the Neoclassical style. The Maitland population during that year rose to 600, and then began to decline during the second half of the decade.
This is another view of the Thurston House visited earlier, providing a good look at the front porch and Queen Anne style woodwork detailing. It also shows the steeply pitched roof and tall chimneys typical of this style.
This Frame Vernacular residence was built in about 1920, when the city's population was 172.
This private home was built in about 1895. Its intricate woodwork exemplifies the Queen Anne style.
A part of the Maitland Art Center, the Research Studio Art Galery was established through Mary Curtis Bok (later known as Mrs. Efram Zimbalist Sr.), a benefactor of Rollins College and other worthy causes.
This facility is a popular location for weddings and quiet breaks from the noise of the city. When established in 1937, it was one of only three art galleries in the state. Andre Smith was the director of the Research Studio from its opening until his death in 1959.
This Frame Vernacular building was constructed in about 1925 as apartments, and remains so today.
This Bungalow was built as a private residence in about 1925. It is now the city's historical museum, acquired by the historical society in 1976, housing artifacts, textiles, and historic photographs from the early days of Maitland. Pioneer settlement, the citrus and lumber industries, churches, schools, and civic organizations are featured.
The Early Telephone Museum, constructed in 1981, commemorates the beginning of the Winter Park Telephone Company by Carl H. Galloway in 1910. The displays include a working switch station and telephones and equipment from the earliest to those in use today.
The Center, with an Aztec-Mayan motif, was built in 1937. It was the winter home of Andre Smith, who was a painter, architect, etcher, author, and outspoken advocate of modern art.
The 22 stucco buildings evolved into an artist's colony, housing studios and living quarters for emerging artists Milton Avery, David Burliuk, Ernest Roth, Arnold Blanch, Harold McIntosh, Ralston Crawford, Doris Lee, and others. The property remained idle from Smith's death in 1959 until 1969, when it was purchased by the city. In January of 1971, the Maitland Art Association formed, leased the property from the city, and opened it as the Maitland Art Center.
A beach on the east shore of the lake was first placed here in 1925 by the Gould Bros. dredge. By 20090, not much snad was left to be called a beach.
This Frame Vernacular home was built in about 1910.
This congregation first gathered in 1958, founded a church with 78 charter members, and built this church complex in 1972. It was designed by architect Hill Stiggins and cost $450,000. They named it after Francis Asbury, known as the "Father of American Methodism".
A Frame Vernacular home was built here in about 1910. It was removed in 2002.
This was the site of the Galloway store, owned an operated by Braxton Allison Galloway. His son, Carl Hill Galloway, started the first Maitland telephone exchange in the back of the store in 1910 with 10 telephones and one switchboard. This eliminated his having to visit his customers' homes to secure orders for goods. He soon moved across the street, next to the post office.
After it burned across the street, a new post office was created on this corner in the 1920s. Directly to the south was J.H. Bennett's Maitland Electric Shop.
This building was constructed in 1925 by A.H. Shadix and housed the Bank of Maitland. In the 1930s, it was Benson's Pharmacy, then a bicycle shop, and real estate office, and again a bank.
Prior to this building, the portion of the site closest to the intersection was the post office. Next to it, now the back half of the bank, was the telephone exchange. The post office and exchange burned in 1923.
The first post office was established for Lake Maitland in 1872, with Christopher Columbus Beasley as postmaster. Beasley built his home next to the Fort Maitland site in 1875. It was bought in 1929 by Mr. and Mrs. E.S. Fournes, who developed it into the winter estate known as "Casa Jaed".
The Chamber was formed in 1924, with J.H. Hill as president. After a period of dormancy, it was revived in 1956. The Chamber's goal is to foster growth among the area's established businesses and lend assistance to new firms and individuals relocating here. Its remodeled building was moved to this site in 1974.
The Pilgrim Packing Co. packing house was built here along the railroad tracks in 1915. It was sold to American Fruit Growers, and burned in 1926. It was rebuilt, and in late 1958 was sold to Square Deal Fruit Company. It burned down again on April 17, 1969.
This building, now housing professional offices, was built in 1925 in the Mediterranean Revival style. A little to the north of this site, facing Maitland Ave., was once the second school in Maitland, a two-room frame building erected in 1884 for 20 pupils in 8 grades taught by Miss Emma Dart. It replaced the first school, a log building on Sandspur Rd.
In the days of Fort Maitland and before, the thoroughfare now known as Maitland Ave. was Black Bear Trail, part of a trail system that stretched from Canada to Tampa Bay.
S.B. Hill Sr. donated land for a school, and in 1923 one was built and named in his honor. By 1926, 75 pupils in eight grades were taught by four teachers in three rooms. It was torn down in 1975.
The Center was built in 1973, and includes facilties for youth, seniors, and the Hebrew Day School. Also included on this site is the Holocaust Memorial Resource & Education Center of Central Florida, built in 1986. This is a source of factual information about the Nazi era, including multimedia displays. Permanent exhibits include The Life Before, In The Camps, Resistance, Final Solution, Liberation, Witness Histories and Local Survivors and Liberators.
Before this home was built, this was the site of the Greenwood Lodge and Home School, a Spanish style house built around a patio in the late 1870s.
In 1906, this home was begun for Sumter Brock Hill, and it was completed in 1908. It included a tower room with 20 windows. That portion of the house burned in 1931 and was not replaced. The estate included a tennis court and bridle paths which wound through its 40 acres.
Under the direction of Rev. W.F. Wallace, ten settlers organized this church on May 16, 1882. They first met in the Methodist church building at the corner of Orlando and Horatio Aves. The first building was erected here in 1883, and showed characteristics typical of the pioneer ecclesiastical architecture of the 1880s. It was built by cabinetmaker David Morrison, and William H. Waterhouse made the pews and donated the bell.
The old sanctuary was torn down in 1967, and the new one was completed in 1968.
The earliest Methodist services were held in Packwood Hall. In 1880, circuit rider Rev. Robert Howren Barnett organized a Methodist congregation, which erected a frame building with a wood shingle roof on this corner. By 1886, Maitland had grown into its own circuit, with four societies. That same year, a parsonage was built. A new sanctuary was built in 1928, but the church disbanded and closed in 1929.
It was known as the Stone House after Forrest B. Stone bought it in the early 1930s and turned it into a citrus packing house. After his death, it stood vacant for years, until it was torn down in 1971.
This Bungalow was built in about 1925.
This building was erected in 1968 and sits near the shore of Lake Minnehaha. Along its eastern shore once was located the Dommerich Estate.
Louis F. Dommerich, a wealthy New York silk merchant, purchased a large estate from Maj. Bolling Robertson Swoope, a Virginia Confederate veteran. Swoope had acquired it in 1874, and had planted the groves and gardens. Swoope was also superintendent of the South Florida Railroad.
Dommerich named his estate "Hiawatha", and of the 210 acres, 138 were landscaped gardens, with the rest planted with oranges. Eight miles of wooden walks passed through azaleas and palms. The Florida Audubon Society was organized here by Louis and his wife, Clara, and had its early meetings at Hiawatha. Their thirty-room frame house was built east of Lake Minnehaha in the early 1890s, and was rebuilt in 1928. It was sold in 1954 for $420,000 to make way for the Dommerich Estates Subdivision.
This Bungalow was built in about 1925.
One of the area's early automobile service stations was located here in the 1920s, owned and operated by Forrest B. Stone.
The present City Hall was built in 1975, replacing the previous one erected in 1925.
The railroad, being laid from Sanford on its way to St. Petersburg, reached Maitland by July 1, 1880. The depot was built here in 1881, taking over railroad station duties temporarily handled by Packwood Hall. The depot was moved from its foundation by a tornado in 1969, and was torn down in May of that year.
Adjacent to the depot to the east was the general store built by G.T. Stith, which housed the first library. Across Horatio Ave. to the north was a boarding house.
Located here along the railroad tracks were the Vanderpool (erected 1892) and Standard Growers packing houses. Behind that was located the Adams packing house. Across Maitland Ave. on the west side stood the Maitland House Hotel.
Built in 1873 by George Horatio Packwood on the first land (40 acres) deeded within the city, this was the center of social life in early Maitland. The first floor was used as a dance floor and skating rink, and from 1880 to 1882 also served as the railroad station. On the second floor were held stage shows, dances and other social events. The third floor served as the town hall, with meeting and office rooms.
In 1879, Edward Turner started a general store in the hall. Methodist and Catholic church services were held here until individual church buildings were completed. Packwood Hall burned down in 1926.
Diagonally across the intersection was located the Maitland Garage, built about 1923 by Joseph Bennett. It was later sold to Roy Kyle.
The library began in 1896, when Clara Dommerich donated about 360 volumes for a library in the home of schoolteacher Emma Dart, the first Maitland librarian. Later, it moved to a room in W.B. Jackson's store next to the railroad depot.
The Maitland Library Association was formed in February of 1907, and completed a 25' x 50' building here in 1909 on land donated by the city. The brick and iron fence was constructed in 1910. Major additions were constructed in 1959 and 1973, and a multipurpose room was added in 1989.
The Center was built in 1965. The community-owned facility offers the use of rooms for luncheons, seminars, business meetings, receptions, and other business and recreational functions.
The building housing the Garden Club was built in about 1925 as a private residence. Stylistically, it is a Bungalow.
William H. Waterhouse came to Central Florida from New York in 1881. During the Civil War, he had been a prisoner of war in Andersonville, Georgia, and thereafter sought a milder climate for his health. It is thought that the lake across the street was named for his wife, Lily.
An architect, carpenter and building contractor, he took a traditional Northeast architectural style and adapted it for the Florida climate. In addition to his own, he also built homes for Charles H. Hall, Randall Bronson, W.H. Johnston, Dr. Haskell, and others. He located his home here very close to the railroad tracks because he frequently received large shipments of lumber and other building materials.
This Victorian style home was built by Waterhouse in late 1883 and early 1884. It has been restored through grants from the State of Florida, Division of Historical Resources, and funding from the City of Maitland and the Maitland Historical Society.
The carpentry shop was built in about 1883, and houses woodworking tools and materials commonly used at the turn of the century, including some owned by Waterhouse himself. Tour guides demonstrate their use.
When built in about 1925, this Bungalow was a private residence. It is now owned by the City of Maitland and is used as offices.
After the Civil War, this body of water was known as St. John's Hole. It was the location of hastily-built shacks housing newly freed slaves. Later, they relocated to more permanent homes to the west, and then to Eatonville.
Anna Hirsch, who wintered with her husband Cyrus in their Lake Ave. home on Lake Eulalia (the Thurston House), directed the Florida Federation of Music Clubs. She also was largely responsible for the beautification of the park surrounding Lake Lily, and upon her death in 1935 it was named the Anna M. Hirsch Memorial Park.
The asphalt covering the old path circling the lake has been stripped off the underlying bricks. They were laid in 1916 as part of the Black Bear Trail/Dixie Highway, which was the first graded brick road in the state.
A History of the First United Methodist Church of Winter Park, by W. Breathitt Gray, Jr. (Ferris Printing Co. 1972)
Boone's Florida Historical Markers & Sites, by Floyd Edward Boone (Rainbow Books 1988)
Chronological History of Winter Park, by Clair Leavitt MacDowell (Orange Press 1950)
Early Houses of Maitland, (Maitland Historical Society 1972)
Eatonville: A Cultural Enigma, by Jessica M. Allen (1994)
Flashbacks: The Story of Central Florida's Past, by Jim Robinson and Mark Andrews (The Orlando Sentinel 1995)
The Florida Audubon Society: 1900-1935, by Lucy Worthington Blackman (Florida Audubon Soceity 1935)
Florida History Through Its Places, by Morton D. Winsburg (Florida State University 1987)
Florida Jewish Heritage Trail, by Rachel B. Heimovics and Marcia Zerivitz (Florida Department of State 2000)
Fort Maitland: Its Origin and History, by Alfred Jackson Hanna (The Rollins Press 1936)
History of Orange County, Florida, by William Fremont Blackman (The E.O. Painter Printing Co. 1927)
The History of Public Education in Orange County, Florida, by Diane Taylor (Orange County Retired Educators Assocation 1990)
Maitland Remembers, by 'Toria Hubbard (Parkland Printing 1978)
Old Tales and Trails of Florida, by Myrtle Hilliard Crow (Byron Kennedy and Company 1987)
Orlando: The City Beautiful, by Jerrell H. Shofner (Continental Heritage Press 1984)
The Pioneer Churches of Florida, by Elizabeth Chase (The Mickler House 1976)
Winter Park Portrait: The Story of Winter Park and Rollins College, by Richard N. Campen (West Summit Press 1987)
Wish You Were Here: A Grand Tour of Early Florida Via Old Post Cards, by Hampton Dunn (Byron Kennedy and Company 1981)
Click here for a copy of the trail rules.