Fincastle, a town with approximately 750 residents, commands attention not because of size but because of history etched into its streets. Founded in the 1770s and named for Lord Fincastle, the eldest son of Virginia’s last colonial governor, it served as a launching point for pioneers heading west. Standing in front of the Botetourt County Courthouse, rebuilt after a 1970 fire but preserving the Jeffersonian ideal of classical order, one senses that this town was not constructed for fleeting moments, but to last.
From the courthouse, the historic district unfolds with nearly eighty-five acres of preserved 18th and 19th-century buildings. Structures like the Ammen House and St. Mark’s Episcopal Church, built in the early 1800s, stand in testament to architectural diversity ranging from Gothic to Federal to Victorian. The Peck House and Selander House provide additional examples, their foundations laid when Virginia’s frontier extended to the Mississippi. Fincastle’s old sidewalks and brick chimneys are not restorations of a time gone by—they are continuations of it.
One of Fincastle’s most unusual cultural contributions lies in its furniture. Jake Cress, a nationally recognized furniture maker, operates a studio here where he crafts historically informed but playfully irreverent pieces. His chairs may sprout wooden fingers or leap with animal legs; drawers sometimes slide open with surprised expressions carved into their faces. His work appears in collections far from Virginia, yet his tools rest quietly in a Fincastle workshop, where visitors can sometimes catch him shaping maple and walnut into grinning curiosities.
Business in Fincastle favors the distinctive over the generic. Cahoon’s Florist & Gifts, a locally owned floral studio, has been providing arrangements and keepsakes to the community for decades, emphasizing in-season blooms and personal delivery. Not far from the town center, Heritage Family Market offers bulk dry goods, homemade jams, freshly baked bread, and hand-sliced deli meats. Operated by Mennonite proprietors, the store also features whoopie pies, hard-to-find spices, and local cheeses from nearby farms, serving both as a market and a gathering place.
When it comes to dining, Fincastle manages to surprise with originality. 1772 Rooftop on Main is a rooftop restaurant and cocktail bar that features a V-tail Bonanza airplane incorporated into its structure. Diners can order blackened shrimp and grits, bourbon-brushed pork tenderloin, and signature cocktails while looking out over the Blue Ridge and courthouse lawn. Around the corner, The Pie Shoppe, also referred to as Fincastle Café, is best known for its savory Chicken Cordon Bleu Pie, Dutch caramel apple pie, and hearty soups served in bread bowls. The spot’s low-key environment and daily-baked pastries have made it a local favorite for more than just tourists.
Outdoor life plays a large role in Fincastle’s rhythm. The Springwood Bike Loop is a 30-mile route that winds through farmland, wooded lanes, and stream crossings, offering cyclists a challenging but scenic route. The surrounding countryside of Botetourt County features multiple entry points to the Appalachian Trail, while shorter hikes like the Button Trail or the segments near Tinker Creek provide more accessible alternatives. Horseback riding and guided canoe trips are also available in nearby stretches of the James River.
Historical walking tours offered through the town include lesser-known landmarks like original wells, cisterns, and family graveyards. On New Year’s Eve, locals gather to ring the courthouse bell—a tradition stretching back more than 150 years. The bell is rung in a set sequence that marks the coming year, and the practice was once recorded by folklorists from the Library of Congress as a notable regional tradition.
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