At Thomas Jefferson’s grand home, Monticello, visitors can learn about the third president’s inventions and interests. The historic site also celebrates the lives of the enslaved people who worked there. Photo © Marcnorman | Dreamstime.com

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Charlottesville’s lively downtown mall has 120 shops and 30 restaurants to choose from. The area is known for its many historic buildings and Civil War sites. Photo © Littleny | Dreamstime.com

Thomas Jefferson dreamed of producing great American wine at his Virginia plantation, Monticello, just outside Charlottesville.

He never succeeded. But today, winemaking is flourishing in central Virginia, with many vineyards in the Charlottesville area.

Exploring the area’s wineries is only one of many reasons to plan a visit. You can tour U.S. presidents’ haunts and a Civil War hospital; amble around Mr. Jefferson’s university; or walk through a historic tunnel built by one of Napoleon Bonaparte’s engineers.

Located less than three hours from Washington, D.C., the area was home to three U.S. presidents: Thomas Jefferson, James Madison and James Monroe, plus two famous explorers, Meriwether Lewis and William Clark, who Jefferson commissioned to explore the Louisiana Purchase.

Monticello and Montpelier

Monticello, the neoclassical home Jefferson designed and completed in 1809, sits atop Little Mountain, two miles southeast of Charlottesville.

The only presidential and private home on the UNESCO list, the domed, three-floor complex has 43 rooms, some with skylights and unique ventilation features. Jefferson drew on Renaissance designs, especially Italian architect Andrea Palladio’s principles.

The home’s front hall displays replicas of the items Lewis and Clark shipped to Jefferson during their famous expedition: antlers, rocks and Indian beadwork.

Outside, the gardens — which combine English, French and Italian designs — reflect Jefferson’s interest in horticulture.

The restored Mulberry Row outbuildings include a woodworking shop, nailery, smokehouse and quarters for enslaved people who worked in the home. During Jefferson’s lifetime, more than 400 people were enslaved on his 5,000-acre plantation, including Sally Hemings, the mother of six of his children.

Montpelier, home of fourth U.S. President James Madison and his wife, Dolley, is about eight miles from Charlottesville. A visit there today reveals 19^th-century plantation life from both the owners’ and enslaved people’s perspectives.

Highland, near Monticello, is the historic home of U.S. President James Monroe, the nation’s fifth president.

Fast forward to the early 1900s and check out Pine Knot, a modest wooden cottage retreat of Theodore and Edith Roosevelt. The Roosevelts escaped Washington’s hubbub in a rail car attached to the mail train, and then journeyed by carriage or horseback to their hideaway in the Albemarle County woods. Open to visitors by appointment only, it is a plain, peaceful place to explore and recharge.

The University of Virginia

Jefferson founded the University of Virginia in 1819 and designed what he called the “Academical Village,” also a UNESCO site, as the heart of the university.

On each side of a white-columned, 740-foot green expanse called “The Lawn” are residential and academic buildings, bookended on the north end by the Rotunda, completed in 1895 and inspired by Rome’s Parthenon.

Being selected to live in a 19^th-century room with a fireplace today is an honor for UVA undergrads called “lawnies.” Visitors can peek into Edgar Allan Poe’s room, restored to his 1826 student days.

The Memorial to Enslaved Workers, dedicated in 2021, honors those who built and maintained the Academical Village. Names of the 4,000 enslaved people who worked on UVA property are etched in the low granite walls of an incomplete circle, which symbolizes a broken shackle.

Downtown and the Tunnel

Charlottesville’s downtown is a walkable dining, shopping and arts district of more than 120 shops, 30 restaurants and theaters in mostly early 20^th-century buildings. A free shuttle links downtown to the university, and parking garages are available.

Adventuresome types can discover groundbreaking engineering in the Blue Ridge Tunnel, a 20-minute drive from downtown Charlottesville. An easy hiking trail leads to the restored 4,264-foot, former railroad tunnel, now a pedestrian tunnel through Afton Mountain’s hard greenstone.

“Until you go there, you just don’t get the tunnel,” Paul Wagner, who directed a documentary about it, told me.

As in the well-known adage, a tiny, captivating, white orb of light at the end of the tunnel becomes larger and larger as walkers amble toward it.

The engineering genius was Claudius Crozet, who, in pre-dynamite days between 1849 and 1859, supervised its grueling construction by 800 Irish immigrants and 300 enslaved men.

Civil War-related sites

Virginia was a Civil War battleground, with many sites preserved today.

Lesser known is Gordonsville’s Exchange Hotel, built in 1860 at the intersection of two rail lines. Trains transported 70,000 wounded Union and Confederate soldiers here when the hotel became the Gordonsville Receiving Hospital.

Today’s visitors can see Civil War medical tools and a war-era blood stain on a table. The Freedman’s Bureau Room honors the “Yankee school marms” who taught at least 250 emancipated people to read and write here post-war.

Wineries and cideries

Although Jefferson never quite mastered winemaking, today 40 wineries abound within 25 miles of the region’s bucolic countryside.

One is the Trump Winery which, with its 45-room Georgian-style luxury hotel, claims to be the largest on the East Coast. Visitors can spend a few hours indoors or outdoors, enjoying the wine, food and scenery.

Cideries thrive, too, such as the Castle Hill Cidery, whose owners brag that their cider saved Jefferson’s life and “won the Revolutionary War.”

In 1781, as British Gen. Banastre Tarleton marched to Monticello to capture then-Governor Jefferson, the farm’s Walker family plied Tarleton with hard cider.

As a soused Tarleton dallied, the Walkers sent a messenger to warn Jefferson that British troops were headed his way. Thanks to their quick thinking and generous service, Jefferson escaped.

For more information, drop by the visitors’ center at 601 East Main St., Charlottesville, or see visitcharlottesville.org, monticellowinetrail.com or virginiacider.org/explore-cideries. Be sure to avoid UVA graduation weekend, May 18 and 19, 2024.