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BROOKSVILLE
(Hernando County)

OLD TIME CITY ON A HILL


For more information about Brooksville and Hernando County, visit: HERNANDO COUNTY CHAMBER OF COMMERCE; CITY OF BROOKSVILLE;HERNANDO TODAY; and HERNANANDO PRESERVATION SOCIETY

BROOKSVILLE, originally known as Melendez and then Benton, is a wonderful city of hills, ranging in elevation from 175 to 274 feet. Coupled with its condensed area (2.77 square miles) and its long history of successful planters, growers, and cattlemen, Brooksville is more a reflection of "the Old South" than other West Coast towns. Brooksville grew from two communities: Fort DeSoto and Pierceville. Its Southern background is reflected in its name, honoring South Carolina Congressman Preston Brooks who is best noted for hitting abolitionist Senator Charles Sumner on the head with his cane.

WHERE TO START: Enter Brooksville from the south on US41 (BROAD STREET), reaching downtown from the east.

Just past Lemon Street, you'll notice on FIRST METHODIST CHURCH, 105 West Broad.

CROSS ORANGE, unless you wish to take a short detour north on Orange to the JOHN J. HALE HOUSE (A), a 3-story 1888 frame house owned by a merchant and railroad trustee. Note how the breezeway that once separated the kitchen is enclosed.

 

At 31 Broad is the PRESBYTERIAN CHURCH BUILDING, converted in 1947 by Henry Carlton Sr. into new location for his grocery founded in 1910.  Up the road at 120 Broad is the DIXIE THEATER (1926), where the only talkies are businessmen doing commerce.

The next intersection is the center of Brooksville. At 1 Main Street is the FIRST NATIONAL BANK (1910), a two-story brick structure with its original cast iron columns.  On the south-side of Broad you should see the massive wall mural of “The Brooksville Raid” by Antonio Caparello.  Brooksville has several neat historic murals in the downtown area.

In the northeast corner stands the HERNANDO COUNTY COURTHOUSE (1913), a rectangular Classical Revival brick edifice designed by William A. Edwards, complete with Ionic columns.

TURN LEFT (north) ON MAIN STREET (later called Howell). At 115 North Main is R.R. DINGLE DEPARTMENT STORE (1912), one of the early large firms. CROSS JEFFERSON STREET. On your left is BACON'S DRUGS (1926) and on your right the notable HERNANDO STATE BANK (1905), where J. A. Jennings was first President prior to its purchase in 1907 by William McKethan.

At 115 North Main is WEEKS HARDWARE (1913), a two-story brick owned by John Weeks, first President of the First Federal Bank. Across the street is the J. M. ROGERS DEPARTMENT STORE (1912), 120 North Main.

 

Downtown Brooksville is very compact but it is quite hilly terrain.

 

Once St ANth Catholic Church * * Lovely Chinsegut Hill Plantation

CROSS FORT DADE. On the right you can stop and get more local information at the CHAMBER OF COMMERCE . 101 Ft. Dade Avenue, or at the nearby  1950  FREDERICK EUGENE LYKES JR LIBRARY.

 

As you go north the road curves and becomes Howell.  At 201 Howell is the 1970 CITY HALL.  At 253 North Main (Howell) is the W. A. FULTON HOUSE (1880), a lovely 2-story double verandah home of the organizer of the Florida Citrus Exchange. Lawyer E. S. MacKenzie was a long owner.  Look carefully to see where the dog trot design once existed.  At 307 Howell is the TANGERINE PLACE (1925), a mission style hotel where in 1931 City Attorney Herbert Smithson was gunned down by rum-runners.

Brooksville's residential streets are lined with interesting buildings, but  SKIP tree-lined IRENE (you see it later) and TURN RIGHT ON OLIVE STREET. At 61Olive is the ST ANTH CATHOLIC CHURCH (1908). nicely converted into a private dwelling. At 48 Olive is the most noted home of GOVERNOR WILLIAM SHERMAN JENNINGS  (1880), originally the Roer House. The three-story frame house has a wonderful octagonal bay tower and is in fine condition.

GO DOWN BROADWAY and turn into IRENE where you’ll love the old road and the W.E. LAW HOUSE (1890) a Colonial Revival at 58 Irene.  The backside of the larger Olive Street houses shows some old barns.

 RETURN TO MAIN STREET, heading south past the Courthouse. At the southeast corner at 2 Broad Street is the J. A. JENNINGS BUILDING (1915), a two-story brick vernacular started by the city's first clerk (1880).

CROSS LIBERTY STREET. At 140 South Main is DOGWOOD STATION (1919), a popular place to shop. At 210 South Main is MONTAINEER ANTIQUES (1925) in a classic Sears & Roebuck catalog house.

TURN RIGHT ON EARLY and drive to BROOKSVILLE/MAGNOLIA. TURN RIGHT to see the fine OWEN WHITEHURST HOUSE (1896), 321 South Brooksville, a two-story double veranda house. TURN AROUND GOING ORTH ON BROOKSVILLE to 133 South Brooksville and the COOGLER HOUSE (1910). Theodore Coogler came from South Carolina as an early settler. Colonel F. B. Coogler was the town's first treasurer (1880).

YOU’LL NEED YOUR CAR TO DRIVE EAST ON LIBERTY:  At Liberty and Saxon Avenue is the famous: ROGER'S CHRISTMAS HOUSE, 103 Saxon Avenue. Mary Roger's Christmas gift shop has grown into an amazing complex of houses filled with decorations, displays, and attractions.

The main house was the 1905 Book Shop  until it started in the Christmas business in 1972.  More historical is the nearby 1864 FRANK SAXON HOMESTEAD, a Queen Anne Revival restored by Margaret Rogers of the store.

VISIT the HERITAGE MUSEUM, 600 West Jefferson, located in the 1850 Stringer House, a Queen Anne masterpiece with a four-story tower. F. L. Stringer was a State Senator and judge. There's exhibits and historic artifacts.

 CHINSEGUT HILL, located five miles north off US41 by Lake Lindsey. Colonel Byrd Pearson of Columbia, South Carolina, founded the plantation. His daughter wed Governor Francis P. Fleming. Colonel Raymond Robins, social economist and Progressive Party leader, owned the estate for years and donated 2,000 acres to the Department of Agriculture. The University of South Florida uses the mansion for private retreats, but the exterior of the house is worth the trip.