By Saundra Amrhein

On a quiet summer morning, a soft breeze stirs the Spanish moss draping vast live oaks surrounding the old mansions in downtown Brooksville near Florida’s west-central coast.

“This is one of the original neighborhoods,” says Kenneth Badgley of the Historic Hernando Preservation Society, driving slowly along Irene Street and other streets lined with brick dating back to the early 1900s.

Many of the houses pre-date the bricks. The estate of late Florida Gov. William Jennings was built in 1891 as a Victorian mansion with a two-story wrap-around veranda and later converted to a Colonial Revival house. Badgley points out the stately mansion’s Queen Anne-style western tower and gingerbread trim.

As one of west-central Florida’s oldest towns formed by white settlers, Brooksville has a large concentration of structures from the 1870s and 1880s, Badgley says.

Remnants of the city’s pre-Civil War origins remain, including a Confederate monument that stands before the county courthouse. The city is named for U.S. Rep. Preston Brooks, who bludgeoned an abolitionist senator in Congress with a cane in 1856, the same year Brooksville became the seat of Hernando County.

The city’s founding families settled here in the 1840s, establishing plantations dependent on slave labor. Some of the buildings from that era – and many more from the late-1800s and early 1900s – are still standing.

Through grass-roots efforts, volunteers at the preservation society have created walking tours to help bring attention to Brooksville's architectural history and awareness for more restoration. Down the block from the Jennings estate, Badgley – the group’s architectural specialist – notes a carriage house or livery stable likely dating to 1887. It’s a white clapboard structure now converted to a two-sided garage.

He passes the Cook-Coogler House, dating from before 1917, originally a one-story Florida Cracker house converted to a two-story bungalow in the 1920s or 1930s, and a completely original Victorian house dating to 1887 — the Burnell-Barnett House — with a two-story veranda wrapping around three sides.

Other historical structures on the walking tour include Classical Revival homes with porch columns and balustrades, the old city hall, the 1885 brick Grimsley country store, a “shanty” possibly dating to the 1840s, service stations from the 1930s, and many others dotting a dozen streets and avenues around historic downtown Brooksville.

To schedule a walking tour of Brooksville or get more information, call Mary Moses at 813-470-0074, Jan Knowles at 352-279-5182 or Jon Yeager 352-608-4221. Tours are free, but donations are welcome.

Nearby Historic Sites

The May-Stringer House is home to the Hernando Heritage Museum at 601 Museum Court in Brooksville. This four-story, 12-gable Victorian house from the mid-1800s is on the National Register of Historic Places. Admission is $5 for adults, $2 for children ages 6 to 12, free for children 5 and younger. Call 352-777-0129.

The Brooksville 1885 Railroad Depot Museum at 70 Russell Street includes a restored 1800s dining car, a 1925 fire truck and displays of items used in early Florida Cracker life. Admission is $3 for adults, free for children. Call 352-799-4766.

Fort Dade Avenue is one of Florida’s scenic canopy roads, rolling under interlacing grand live oaks and stately pine trees. It runs north of and parallel to U.S. 41 or Jefferson Street through downtown Brooksville. Go west and drive toward Old Spring Hill and the original antebellum homestead of the Lykes family, which became one of the nation’s largest landowners and had business interests that ranged from cattle to citrus juice. Also along this road where it bends toward State Road 50 are three cemeteries, including the Spring Hill African-American Cemetery, where slaves and prominent black residents were buried dating back to the Civil War.

Chinsegut Hill Manor House has undergone massive restoration following a $1.5 million state grant in 2013. Listed on the National Register of Historic Places, it sits on 114 acres on one of the highest elevation points in the state, about six miles north of Brooksville on land originally developed in the mid-1850s as part of a sugar plantation using slave labor. Later estate owners hosted such notables as Thomas Edison, Helen Keller and Marjorie Kinnan Rawlings. The nonprofit Friends of Chinsegut Hill has worked to restore the property and unearth its history through archeological exploration encompassing ruins of field houses and slave quarters. Call 352-799-5400 or visit


Places to Remember