Gillespie County can be explored through several distinct themes: history in Fredericksburg, a route to 17 historic rural schools, wineries between the highway and downtown, and scenic back roads. For planning, it helps to choose your focus early: Would you like to explore buildings and local history, follow a driving or cycling route, or take in the road scenery and wineries?

Museums and Historic Trails

The Historic Jail in Fredericksburg is Gillespie County’s fourth jail and was built in 1885. The Pioneer Museum in Fredericksburg offers another way to explore history: its ten historic buildings illustrate various aspects of the county’s history. The jail is a single building with a specific construction date and place in the sequence of county jails; the museum complex presents several historical themes through different buildings. Audio and virtual experiences connect visitors to the Pioneer Museum with descendants of the first German settlers.

On the Gillespie County Country Schools Driving and Cycling Trail, visitors can tour 17 historic rural schools by car or bicycle. Many of the schools along the trail are listed on the National Register of Historic Places and are recognized by the Country School Association of America. Free trail maps are available at the Fredericksburg Visitor Information Center. Since route details and map distribution can change, it is advisable to check for current information before your visit.

Another historical connection is the Pinta Trail: it ran north from the south along the Grape Creek watershed into Gillespie County. Unlike the rural school route, this trail focuses on a historic route.

Wineries, Roads, and Geographic Orientation

The range of wineries extends from operating wineries along Highway 290 to urban tasting rooms in downtown Fredericksburg. For trip planning, this creates a practical distinction: highway locations on one hand and a downtown setting on the other. If you would like to include wine in your trip, you can decide which setting better suits your plans.

Gillespie County’s back roads offer miles of scenic routes for road cycling. If you plan to ride a road bike, you can include this scenic option in your plans. Since road and cycling conditions can change, check current conditions before setting out.

Peach stands line many of the roads leading into Fredericksburg. They are especially plentiful on Highway 290 between Fredericksburg and Stonewall, as well as on Highway 87 South.

The location of Enchanted Rock State Natural Area also helps put the region on the map: it lies on the boundary between Gillespie County and Llano County.

Discover more destinations: Castro County, Mcculloch County, Ector County, Dickens County, Comanche, Mitchell County, Eastland County, Bastrop

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