Enterprise Historical TrailEnterprise Historical Trail


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.

Enterprise Historical Trail

Copyright 2006 by Steve Rajtar

(From Interstate 4, drive east on DeBary Ave., south on Main St., and east on Lakeshore Dr. (which becomes Enterprise-Osteen Rd.) past Providence Blvd. to park at Mariners Cove Park. Walk east on Enterprise-Osteen Rd. 750 feet past Stillbrook Trail.)(0.8 miles so far)

North side of Enterprise-Osteen Rd., between Stillbrook Tr. and Barker Dr.

1....Disciples of Christ Church

An African Methodist Episcopal congregation organized in 1881. A church building was completed here in the late 1880s and was named after St. Paul. Pastor Rev. A.A. Fleming supervised the congregation in the construction of a schoolhouse, completed in about 1890. The church was rebuilt in 1948 while Rev. S.D. Shaw was the pastor. It was later known as the Enterprise A.M.E. Church and, in about 2000, became the home of Iglesia Christiana de Deltona.

(Continue southeast on Enterprise-Osteen Rd., then walk south on Stone Island Rd. to the south end of the median road island, just after crossing Bethel Creek.)(1.5)

Stoen Island Rd., south of Bethel Creek

2....Stone Island

This area was once known as Doctor's Island, and then Rock Island. It was visited by John Bartram in 1766, when he was sent here by King George III to conduct a survey. Another early visitor here was count Louis Francois de Pourtales, who worked with the tidal department of the U.S. Coast Survey. He was a pioneer in deep-sea dredging and found a human jaw and other bones on the island.

(Continue south on Stone Island Rd. to the intersection with Horse Shoe Rd. Continue west on Stone Island Rd. to the intersection with Shellmound Rd. Continue south on Stone Island Rd. to the intersection with Sunset Rd.)(2.3)

Intersection of Stone Island and Sunset Rd.

3....Site of Fort Kingsbury

Located near here for about six weeks was a temporary army post known as Fort Kingsbury. It was named after Lt. Charles K. Kingsbury of the Second Dragoons, who fought in the battle of Camp Monroe in February of 1837, and later died of fever.

The precise location of the fort was a mystery until 1970, when evidence of it was discovered during the development of this community.

(Walk south, west and northwest on Sunset Rd., and west and north on Warrior Tr. to the intersection with Kettledrum Tr. and unmarked Arrowhead Tr. Walk east on Arrowhead Tr., north on Stone Island Rd., west, northwest, and west on Enterprise-Osteen Rd. (which becomes Lakeshore Dr.) to the Deltona Civic Association building.)(5.6)

North side of Lakeshore Dr., between Hanging Moss Ln. and Providence Blvd.

4....Site of Old Enterprise

This area was originally settled by Cornelius Taylor, a former timber agent from St. Pablo, Florida. He moved here in 1841 and the following year filed for homestead on 160 acres, living on the western edge of the settlement. A post office was established in 1845 with Ora Carpenter as its postmaster.

During the 1840s, Enterprise was considered to be a health resort with three sulphur springs. The Lower Salt Sulphur and Green Spring still exist, but the Upper Salt Sulphur Spring probably disappeared during the earthquake of August 31, 1886.

In 1843, Taylor was elected as a state legislator, and introduced the bill which resulted in Enterprise becoming the county seat of Mosquito County. Two years later, this became Orange County and the county seat moved to Mellonville. In 1854, Volusia county was created with Enterprise as the county seat.

Taylor moved away following a typhus epidemic that killed his daughter and nine slaves, and drowned on the way to California by ship in 1849. Later, the property was acquired by Dr. James Starke. It passed to his heir, John W. Starke, by 1867. By that time, Enterprise had a dry goods store, bowling alley, hotel, courthouse and a blacksmith shop.

Starke built a home, called "Bueno Retiro", on a knoll near the lake. In the yard was a marble grave marker for Polly, the 13-year-old daughter of the Taylors. She was the first white person buried south of St. Augustine.

(Continue west on Lakeshore Dr. to the intersection with Broadway St., and look to the north.)(6.2)

Broadway St., from DeBary Ave. to Lake Monroe

5....Storer Subdivision

In January of 1885, F.A. Story subdivided both sides of Broadway into 40 separate lots.

(Continue west on Lakeshore Dr. to the two-story brick and wood siding building.)(6.4)

North side of Lakeshore Dr., between Broadway and Main Sts.

6....Randall/Frantz Hall

This building was erected in 1933 and named the Randall Boys Hall, as it was a gift of Mr. and Mrs. James D. Randall. When it was renovated in 1982, it was renamed to also honor donor E. Harold Frantz. It has recently served as a day care center called "In As Much."

(Continue west 250 feet on Lakeshore Dr.)(6.5)

North side of Lakeshore Dr., between Broadway and Main Sts.

7....Site of Brock House

In 1852, Capt. Jacob Brock, the "Father of the steamboat lines on the St. Johns River", bought 140 acres and a frame store building. In 1856 he built one of the earliest inns in Central Florida, modeling it after hotels he had seen in New England. Named the Brock House, it accommodated the passengers on his steamboats, the Darlington and the Emma Brock.

The hotel was situated on a slight rise near Lake Monroe, overlooking an orange grove to the west which was mature by 1867. The hotel was 110 feet long, two and a half stories tall, with an open porch facing the lake.

Brock sold his property in 1876 to Luther Caldwell, who sold it the same year to the firm of Bodine & McCarthy. They renovated the hotel, added a 1,000-volume library and new furnishings. In was a winter resort and a sportsman's paradise. In 1910, it operated as the Epworth Inn.

Brock had built a steamboat wharf for $300 in front fo the hotel. Remnants of old wooden pilings from it may still be found in the water in front of the present administration building of the Florida Methodist Children's Home.

A later owner of the hotel changed its name to the Benson Springs Inn, and petitioned guests and employees to change the town's name to match it. As a result, the town was named Benson Springs from 1927 until 1937. The Children's Home bought the Brock House in 1937 and demolished it. During that same year, a petition was circulated among school children to get sufficient signatures to again change the name of the town, which returned to Enterprise.

(Continue west on Lakeshore Dr., then walk north on Main St. to the brick and iron entrance gate.)(6.7)

East side of Main St., between Lakeshore Dr. and DeBary Ave.

8....Florida Methodist Children's Home

This home for children was organized in 1908-09 as the Florida Methodist Orphanage, and now encompasses 100 acres including the site of the Brock House and the homestead of William Thayer.

The Smith Hardin Hall was built here in 1927.

(Continue north on Main St. to the intersection with DeBary Ave.)(6.8)

Southeast corner of DeBary Ave. and Main St.

9....Site of General Store

During the 1880s, a two-story general store and post office was located here. It was bought and torn down by the Florida Methodist Children's Home.

Also at this intersection was the Thayer and Sauls Store. William S. Thayer moved to Enterprise with his family in 1865 and opened a store here with John Sauls in 1872.

Thayer bought the property of Elijah Wilson in 1878. He was elected to the state legislature in 1895 and was reelected in 1897. Thayer rented a 15-person cottage to guests for $12-15 per week. His property is now a part of the FMCH complex.

In 1883, Sauls and Mr. Quackenboss operated a stage or hack to the east coast.

(Walk west on DeBary Ave. 350 feet past Enterprise St. and look to the southwest.)(7.0)

South side of DeBary Ave., between Enterprise and Maple Sts.

10....George E. Turner Power Plant

The power plant here was built in 1924 by the Florida Public Service Co., which later became Florida Power Corporation.

(Walk easton DeBary Ave. to the intersection with Clark St.)(7.2)

Northeast corner of DeBary Ave. and Clark St. (155 Clark St.)

11....All Saints' Episcopal Church

Rev. Samuel B. Carpenter from the Holy Cross Episcopal Church in Sanford assisted in the formation of the All Saints' Mission in 1881. A church was built near the lake in 1883, using donations from Frederick deBary and Arthur K. Benson of Montauk Point. The stained glass windows date to 1884.

The one-story church has a Gothic Revival style. It is one of the oldest of the original Episcopal mission churches in Central Florida. It was placed on the National Register of Historic Places on May 3, 1974.

(Walk north on Clark St. and east on 3rd St. to the northeast corner of the intersection with Main St.)(7.4)

East side of Main St., near 3rd St.

12....Site of Courthouse

In 1870, Jacob Brock donated a 361 foot square lot to the county as a site for the second courthouse. Its construction cost $2,650. The courthouse was converted into the Enterprise Elementary School after the county seat moved to DeLand in 1888.

The building was sold to the Board of Public Instruction in 1891 for $3,975, and was used as a school. In about 1916, the student population was too low to justify a class, so additional children were brought in from Fort Florida.

The first courthouse was torn down in 1917 and the lumber was salvaged to be used in its two-story replacement on the same site.

(Walk north 100 feet on Main St. and look to the east.)(7.4)

East side of DeBary Ave. north of 3rd St.

13....Site of Enterprise Grade School

The Enterprise grade school had one teacher who taught grades 1-8 until about 1909, when it was increased to two. The school was renamed Benson Springs in 1927 and had students in grades 1-10. At the time, the school consisted of the old 1917 courthouse, and what later became the Physical Education Hut. The front part of the latter was used for a lunchroom and the back was the boys' shop. It was still in use as a school when it burned in the 1960s.

(Look to the north.)(7.4)

Between Watson and Sauls Sts., including Lexington, Lincoln, and Livingston Aves.

14....Site of Watson Homestead

Elijah Watson in 1867 bought one of the town lots developed by Brock for $2,600, and built a dry goods store. He had a successful business, dealing with the 486 residents of the time. Watson also operated a steam-powered cotton gin, sawmill and grist mill. In 1854, he had been appointed the first sheriff of Volusia County.

The railroad ran diagonally through this property. It was subdivided by Watson's heirs after his death in December of 1886.

(Walk south on Main St. and east on 3rd St. to the intersection with Court St. and look to the northeast.)(7.5)

East of the courthouse site

15....Bodine & McCarty Subdivision

This firm purchased the Brock House in 1876 and acquired ten additional acres. They developed and subdivided the area from Court St. and Elizabeth St. east of the courthouse, and between 3rd St. and Lexington Ave.

(Walk south on Court St. to the intersection with DeBary Ave.)(7.6)

Northeast corner of DeBary Ave. and Court St. (710 DeBary Ave.)

16....Post Office

Enterprise obtained a post office in July of 1866. Samuel F. Calhoun served as the first postmaster. Enterprise incorporated on February 1, 1877, with William Thayer serving as its first mayor.

(Look south across the street.)(7.6)

South side of DeBary Ave., between Main and Court Sts.

17....Site of Arcade Building

Located near here was a two-story arcade which housed the Wakefield Preserving Co., producing homemade marmalades, jellies and canned fruit. It was built in 1884 and was given to the Barnett Memorial Church in 1933 upon the condition that it be removed by the end of that year. It was torn down and used for lumber, some of which was used in the construction of the Methodist Church's educational annex.

(Walk east 75 feet on DeBary Ave. and look across the street to the south.)(7.6)

South side of DeBary Ave., between Court St. and Madison Pl.

18....Barnett Memorial United Methodist Church

Enterprise's first formal Methodist church service was held in 1908. Later services were conducted in members' homes, on the Brock House lawn, dock and hotel, in the orphanage's chapel and social hall, in the old arcade, and in the Community Building. In 1923, the orphanage donated a lot for a church.

In 1929, money was raised to erect a church building, but the $900 was lost when the bank closed. More money was obtained by Rev. R.H. Barnett, and the church dedicated in 1931 was named after him. When the Brock House was torn down in 1937, its main staircase was added to this church. The benches came from a Presbyterian church, which disbanded after a fire.

(Continue east on DeBary Ave., then walk south on Providence Blvd. and east on Lakeshore Dr. (becomes Enterprise-Osteen Rd.) to the point of beginning.)(9.8)


A Guide to National Register Sites in Florida, (Florida Department of State 1984)

A Pictorial History of West Volusia County 1870-1970, by William J. Dreggors, Jr. and John Stephen Hess (E.O. Painter Printing Co. 1989)

Discover Florida: A Guide to Unique Sites and Sights, by Robert Tolf (Manatee Books 1982)

Florida Historic Markers & Sites, by Floyd E. Boone (Gulf Publishing Company 1988)

Florida Historic Stained Glass Survey: Sites of Historic Windows in Public Facilities in the State of Florida, by Robert O. Jones (Florida Members of the Stained Glass Association of America 1995)

Florida's History Through Its Places: Properties in the National Register of Historic Places, by Morton D. Winsberg (Florida State University 1988)

Florida's Past: People and Events That Shaped the State, by Gene M. Burnett (Pineapple Press 1988)

Guide to Florida's Historic Architecture, (University of Florida Press 1989)

History of Volusia County, Florida, by Pleasant Daniel Gold (The E.O. Painter Printing Co. 1927)

History of Winter Park United Methodist Church, by W. Breathitt Gray, Jr. (1970)

Hopes, Dreams, & Promises: A History of Volusia County, Florida, by Michael G. Schene (News-Journal Corporation 1976)

Reflections: West Volusia County, by M.E. Ross et al. (1976)

Volusia: The West Side, by Arthur E. Francke, Jr., Alyce Hockaday Gillingham, and Maxine Carey Turner (West Volusia Historical Society (1986)

Click here for a copy of the trail rules.