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

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

Visit the Monticello Wine Trail

Over two hundred years ago Thomas Jefferson imagined that local wines could rival the best of the Old World. Today that vision has become a reality. Charlottesville Guide’s Winery Guide lists many of the area’s leading vineyards that comprise the Monticello Wine Trail. In particular, we like a loop near Monticello itself, where old Virginia history and numerous, new Virginia vineyards await the curious and the thirsty. Here are four recommendations for adventure and discovery in a three hour excursion just south or town.

Up along the Saunders-Monticello Trail to Michie Tavern & Monticello

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.

Around the Bend to Visit the Last of the Founding Fathers

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.

Reward yourself at the Tasting Room & Taphouse of Mount Ida Reserve

An excellent option to relax after touring is the extravagant Mount Ida Reserve, at once both a brewery and a winery with an elegant tasting area and grounds that sweep into the countryside as famous to early Virginians as it is to us today. Wind down here or if you’re itching to get back to town, check out these recommendations for restaurants near Monticello.