Charlottesville: History in the Hills

Charlottesville is a city with a rich past and a dynamic present.

From its involvement in the Revolutionary and Civil wars, to Jim Crow Law hardships, to the “Unite the Right” white supremacist rally in August of last year, Charlottesville is a hotspot for events that, for better or worse, have long held a mirror up to the nation’s political and social conflicts. But, for visitors and residents, what’s good about the area decidedly outweighs the bad.

Nestled in the foothills of the Blue Ridge Mountains, Charlottesville is surrounded by rolling hills brimming with vineyards and wineries, orchards and hiking trails including the nearby Shenandoah National Park. It’s a dream destination for foodies, history buffs and nature lovers.   

Rural attractions complement a vibrant urban center. Restaurants, bars, shops and cultural activities flourish within the Downtown Mall, a brick-lined pedestrian area in historic downtown Charlottesville. The mall hosts eclectic music and arts events throughout the year, making it a perpetually popular hangout spot.

Charlottesville’s diverse cultural scene is the product of a storied history, one you can learn about at any of its many museums, on walking tours and at historic sites. Perhaps the most noteworthy of these is Monticello, the home of Thomas Jefferson, a founding father, author of the Declaration of Independence and the nation’s third president.

Old world meets new in Charlottesville’s top-notch public college, the University of Virginia, founded in 1819 by Jefferson himself. The university proffers its own air of youthful spirit, as well as graduates who make a difference in many fields. 

Get to know the history of a charming, picturesque city with prominence in political and cultural spheres while sampling some of the state’s best food and wine. You’ll find that Charlottesville’s brimming with adventure.

EAT

Commonwealth Restaurant and Skybar

With a menu comprised of local, seasonal ingredients in dishes curated by a team of talented chefs, Commonwealth offers a modern space for customers to enjoy lunch, dinner and brunch. Dine at the Library Bar, in the dining room, or on the rooftop Skybar, with views of the Downtown Mall. Top dishes include Cider Braised Littleneck Clams, Heirloom Tomato Carpaccio, Pimento Cheese Pork Rinds, and Chicken and Waffles served with Sausage Gravy and Fried Potatoes. commonwealthskybar.com

Sultan Kebab

For authentic Turkish cuisine, Sultan Kebab’s menu takes inspiration from the historic kitchens of the Topkapi Palace in Istanbul. Traditional fare includes Grilled Halloumi Cheese, grilled and served with seasonal greens; the Adana Kebab Sandwich, filled with skewered, grilled, Turkish-spiced ground beef on Lavash bread with lettuce, tomato and onion, and Kuzu Pirzola, which consists of grilled lamb chops over a bulgur wheat pilaf. Don’t forget to pair your meal with a Turkish wine. sultankebabcville.com

Splendora’s Gelato

For dessert, stop into Splendora’s Gelato, a popular cafe on the Downtown Mall that offers
artisanal Italian gelato and espresso drinks and other dessert specialties. Splendora’s Gelato combines milk and cream from a Virginia dairy with ingredients such as ground nuts, cocoa powder, pure vanilla and fresh fruit purees, omitting any artificial flavors or food colorings. Rotating popular flavors include Milk and Cherry, Dulce de Leche, Cookies & Cream and Stracciatella, a traditional Italian flavor made made of a milk-based gelato and chocolate shavings. splendoras.com

DRINK

Barboursville Vineyards

Located a half hour outside of Charlottesville, the Barboursville Vineyards and estate date back to the 18th century. Owned by the Zonin family from Veneto, Italy, the vineyards feature Old World wines as well as historic ruins on picturesque grounds. Wine connoisseurs celebrate the vineyard’s renowned blends, including the flagship Octagon Red Bordeaux and the Paxxito, reflecting centuries of the Virginia Piedmont’s climate. bbvwine.com

Castle Hill Cider

Castle Hill Cider is home to award-winning ciders crafted from apple trees on 600 acres in the Charlottesville countryside. The cidery combines new and old techniques, including pressing apples on an American-made press, to produce a variety of seasonal offerings, including Terrestrial 2016, a crisp blend of Winesap and Albemarle Pippin apples, and the Library Selection Celestial, which combines Pippin, Winesap, Grimes Golden, Ashmead’s Kernel and English Bittersweet apples for a spicy, citrusy cider. castlehillcider.com

Lost Saint

Lost Saint is a basement speakeasy known for its creative, humorously named cocktails. The intimate bar is renowned for special drinks created for holidays and events and it maintains an ever-changing drinks menu. Try the Filibutter Old Fashioned, concocted with peanut butter and raspberry-infused bourbon; The Underwood Solution, a smoked whiskey cocktail reminiscent of a Manhattan, and The Undaunted, a combination of Ketel One vodka, Plymouth gin, Bacardi Ocho, demerara syrup, lemon juice and Averna soda. lostsaintbar.com

DO

Carter Mountain Orchard

October is peak apple-picking season, and Carter Mountain Orchard is a favorite destination. You’re free to pick your own apples from the seemingly endless acres of fruit trees, amid awe-inspiring views. The Bold Rock Cellar onsite offers hard cider, crafted using Carter Mountain apples, to sample and purchase. chilesfamilyorchards.com/orchards/carter-mountain-orchard

Monticello

Thomas Jefferson’s estate gives a glimpse into the former president’s home life, with tours of the house and its surrounding gardens available several times a day. Visitors can learn about the nation’s history of slavery on a tour focused on the experiences of the enslaved people who lived and worked on Monticello’s plantation home. monticello.org

Skyline Drive

The 150-mile Skyline Drive, a National Scenic Byway, traverses Shenandoah National Park, with astounding views of the surrounding Blue Ridge Mountains—especially during fall, when the leaves change from golden yellows to burnt oranges and vibrant reds. Take in the Virginia mountains’ beauty at 75 scenic overlooks located along the route. visitskylinedrive.org

STAY

Oakhurst Inn

A boutique hotel in the heart of historic Charlottesville, the Oakhurst is quaint and elegant, with 27 modern guest rooms, five furnished apartments and a gourmet cafe only steps from where the town and university meet. The inn provides a complimentary trolley ride to transport guests to the historic Downtown Mall. oakhurstinn.com

Boar’s Head Resort

Southern elegance and modern luxury combine in this award-winning retreat, with 175 rooms and suites, a restaurant, luxury spa, swimming pool, golf course, trail system, and sports club. The resort sits atop the Blue Ridge Mountains, with gorgeous views to wake up to. boarsheadresort.com

The Inn at 400 West High

This cozy bed and breakfast, just a short walk from downtown Charlottesville, offers unique, individually-decorated rooms with welcoming, whimsical bedspreads and plush pillows. The inn provides a freshly prepared breakfast daily, served with a local Shenandoah Joe Coffee Roasters blend. 400westhigh.com