Discover the Monticello Trail (a 3-hr. adventure near Charlottesville)

The Monticello Trail


The Monticello Trail is a Gateway to Adventure and Culture

Curious about historic Charlottesville but have limited time to explore? History, Wine and Culture await your excursion! The Monticello Trail is Charlottesville’s red carpet of Jeffersonian past and wine-tourism future. Go now and return before anyone has missed you!


1. Close to Town

Just south of downtown on Route 20, motorists can head up the Thomas Jefferson Memorial Parkway, while those seeking exercise can park and take the Saunders-Monticello Trail, which travels uphill roughly 2.5m to Jefferson’s doorstep. On the way, make note of Michie Tavern, ca. 1784, just before Monticello’s entrance, where you can “get a taste of the 18th Century.” Famous for their period ambiance, fried chicken and now their pre-Revolutionary pub (think un-sports bar), Michie’s (pronounced like Mickey Mouse) is an ideal complement to an historic house tour.

Of course, Monticello is the #1 most popular attraction in Charlottesville. The talented staff there, led by Leslie Greene Bowman, has transformed the traditional house tour into a medley of indoor and outdoor experiences, including the July 4th Naturalization Ceremony and the Heritage Harvest Festival in October.


2. More History Awaits

Just 3 miles around the bend from Monticello awaits James Monroe’s Highland. Home to our 5th President — the very one who bought Florida from the Spanish — Highland was home to Madison and his family from 1799 – 1823. Today the house and grounds tours continue to evolve with archeological findings to pepper the experience.


3. Wineries we recommend along this stretch of The Monticello Trail

Only two miles past Monticello you’ll find Jefferson Vineyard, a lovely wine experience hosted by a longtime area wine family in the Simeon area at the top of The James Monroe Parkway. Further along the Parkway heading toward Carter’s Bridge, you’ll pass the sleek, architecturally-modern tasting room of Gabrielle Rausse, one of Virginia’s leading vintners and also chief curator of Monticello’s gardens. Nearby we recommend Blenheim Vineyards, owned in part by Dave Matthews, or Trump Winery, owned in-part by the former POTUS

For yet another extravagant wine and country experience, we recommend a little further on the Tasting Room and Taphouse at Mount Ida Reserve.


4. Michie Tavern for the Ultimate Close

Once you’ve made this grand tour around Albemarle’s Horn of History, you may experience sensory overload. In that case we have only one recommendation: Go All In! You can do that by returning to Monticello Mountain to find Michie Tavern. This throw-back tavern dates to the Jeffersonian era, and the staff that greets you wear period costumes. The hard wood floors and dim interior light set the mood for either a delightful beverage in the 1784 Pub or full-blown meal served downstairs in the dining room. Be sure to find the golden fried chicken. It’s considered the best in town!


See our Complete Guide to Area Wineries here.