Hiking Through History

Traverse a collection of the best trails through the scenic estates of our Founding Fathers.

Charlottesville, Va., has a vibrant past that dates back to the various tribes who once called the land home, from its first inhabitants (the forefathers of the Sioux and Cherokee peoples) to the Monocans, upon arrival of Europeans in the 1500s. While the settlers established homesteads, the mid-sized Virginia city gained its outsized historic stature as the United States was claiming its independence, with several of the Founding Fathers residing in Charlottesville. Today, you can visit the homes of three of our first Presidents. And while you can experience what life was like in their preserved homes, the real boon to active hikers and runners are the palatial estates of these properties. Featuring expansive grounds with well-established trails, these landmarks layer another reason to explore the area’s terrain, get a little exercise, and learn more about this pivotal time in American history. Here are three of the best hikes traversing the estates of our Founding Fathers. 


Thomas Jefferson certainly left his fingerprint on the U.S., penning its Declaration of Independence before becoming the country’s third president. He also founded the University of Virginia, which helps define downtown Charlottesville today. He spent 40 years designing and overseeing the completion of his estate, Monticello, a 43-room, 11,000-square-foot, neoclassical-style architectural wonder that’s surrounded by botanical, fruit, and vegetable gardens. It’s the only home in America that’s designated by the United Nations as a World Heritage Site. There’s also more than 200 acres of forest and farmland to explore via 7 miles of developed trail

The Saunders-Monticello Trail is the main thoroughfare, running for 2 miles adjacent to the Thomas Jefferson Parkway, connecting Kemper Park with the entrance gate to Monticello. The path is a mix of gravel, boardwalks and more primitive paths, passing by a 2-acre pond before gently climbing the side of Carter Mountain. Hiking the trails is free, but visiting the house and gardens requires a ticket ($32, adult). You can also tack on tours of the house ranging from family-friendly romps that explore the nuances of the architecture and Jefferson’s accomplishments to more in-depth looks at the role of slavery on the property. More info: monticello.org


James Monroe might not be as famous as his contemporary, Thomas Jefferson, but he had a distinguished political career that included negotiating the Louisiana Purchase and becoming America’s fifth president. His home, Highland, was a working plantation that was eventually purchased and restored by The College of William & Mary. It’s still a working farm, and the college has worked to uncover the true history of the home and its grounds with a special focus on detailing the lives of enslaved men and women who were responsible for its success. 

The Highland Rustic Trails are a collection of 6 miles of trail meandering through the forest adjacent to the plantation. The Mountain Trail is a 2.5-mile loop that takes in much of the forest. There are no dramatic views along the trek, but it’s less crowded and manicured than the trails you find at Monticello, plus you’ll have the opportunity to see local fauna; wildlife cameras have captured black bear, turkey and fox recently. Hiking the trails is free, but you’ll need tickets ($16, adult) to visit the house. More info: highland.org


James Madison was the fourth president of the U.S. and considered the father of the Constitution and author of the Bill of Rights. Montpelier was his lifelong home and centerpiece of the 2,650-acre property. The trails are arguably even more stunning than any of the historic structures, as more than 8 miles of paths traverse horse pastures, meadows and an old-growth forest. You’ll need a property pass to hike the trails ($12, adult). The 3.5-mile Montpelier Loop Trail gives you the full scope of the property, starting at the M. Rubenstein Visitor Center and running past the Annie duPont Formal Garden before entering the old-growth Landmark Forest, where you’ll see 150-year-old tulip poplars and white oaks. You’ll also hike past the Montpelier slave cemetery and Madison family cemetery. More info: montpelier.org

Post-History Refreshments 

Michie Tavern is a colonial-era tavern established in 1784 in what was a relatively wild portion of Albemarle County, surrounded by the Blue Ridge Mountains. It was the social center for the countryside, and served as a post office and occasional schoolhouse. The building was moved from its original home to its current spot near Monticello in the 1920s. Now, it’s the centerpiece of a group of reassembled historic buildings that includes a restaurant, pub and set of stores. Grab an authentic lunch of fried chicken, mashed potatoes and green beans after your hike, or a frothy pint of local ale in the 18th century-style pub—one that’s decked out in period-appropriate decor, including antiques, games, and even the garments of ye olde servers. More info: michietavern.com

All articles are for general informational purposes.  Each individual’s needs, preferences, goals and abilities may vary.  Be sure to obtain all appropriate training, expert supervision and/or medical advice before engaging in strenuous or potentially hazardous activity.