The Best of Charlottesville, Virginia

In Charlottesville, the influence of Thomas Jefferson looms large. The University of Virginia, which he founded, and Monticello, the fascinating house he built and rebuilt over many years, are the city’s two must-see sites. It’s a sophisticated, intellectual city that appreciates the best of everything—food, music, art, design, and sport—and revels in its beautiful setting. The gorgeous surrounding countryside offers scenic drives and destination restaurants, wineries, farms, and inns.

Charlottesville, VA, VA, USA
A work in progress throughout his adult life, Monticello truly reflects Thomas Jefferson’s many passions: architecture, philosophy, science, music, literature, art, and food. Check out the excellent visitors’ center first and take a shuttle to the mountaintop mansion with its expansive views. A guide takes you through the main-floor rooms, including Jefferson’s bedroom/study/library. Then explore the cellars, terrace walks, kitchen, thousand-foot vegetable garden, and Mulberry Row, where ongoing reconstruction illuminates the important roles slaves played at this complex and innovative plantation. Order timed tickets online for your desired date. Hours vary by season.
Charlottesville, VA, USA
Stretching for seven blocks along University Avenue and West Main Street, The Corner is home to Mincer’s, selling UVA sportswear and accessories, Paul Victorius, selling historic prints, and dozens of restaurants and nightspots including Bodo’s Bagels, The College Inn, Littlejohn’s New York Deli, the venerable Virginian, and the classic greasy spoon diner White Spot. The stylish Graduate hotel is conveniently close to campus.
1435 Carters Mountain Trail
Head five miles out of town for great scenery and a fun family outing. Pick your own seasonal fruits and vegetables (or buy them at the farm stand) and enjoy casual farm-to-table dining, Prince Michel, wines and Bold Rock hard cider—all with an impressive view. Thursday evenings until 9 p.m. from May through September feature dinner, live music, hayrides, and memorable sunsets. The Apple Harvest Celebration starts in September.
515 Water St E, Charlottesville, VA 22902, USA
The C&O has been a mainstay of Charlottesville fine dining for decades. The vegetable soup and Steak Chinoise are justifiably beloved, but you really can’t go wrong with anything on the French- and Southern-influenced menu. The historic building has exposed brick walls, creaky floorboards, and six dining areas, including a patio, to accommodate both special occasions and casual dinners.
200 Ednam Dr, Charlottesville, VA 22903, USA
A bucolic resort in the Virginia Piedmont, the Boar’s Head Resort is as deeply rooted in Virginia as its owner and neighbor, the University of Virginia. The land has hosted travelers since 1759, with the original Birdwood mansion dating to 1830. A short drive from downtown Charlottesville, Boar’s Head has plenty to keep a visitor occupied without even leaving the property, including an 18-hole golf course, a full-service spa, a fitness center with squash and tennis courts, and three swimming pools. The resort has 175 rooms spread over 573 acres; suites feature a seating area and balcony or patio, and some have fireplaces. Dining options range from healthy café fare (necessary fuel for all those tennis matches), to a grill overlooking the golf green, to an elegant meal in the restored Old Mill Room. The Blue Ridge mountains are renowned for their fall foliage, but visit in summer for fewer crowds (and UVA students) and the English-inspired grounds and gardens in full bloom. Be sure to ask for details on arranging a hot-air balloon ride over the countryside to appreciate all of historic Virginia.
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