Set among the Blue Ridge Mountains in Virginia, Charlottesville is a must-visit destination. While best known as home to the University of Virginia (UVA) and Thomas Jefferson’s estate, Monticello, the charming city is a treasure trove of wonders—from exceptional antique shops to an ever-growing food scene.
And I would know—I recently had the pleasure of exploring the city on a tour with the Institute of Classical Architecture and Art and Classical Excursions, alongside a star-studded roster of interior designers, all of whom flocked to Charlottesville for its shops, hotels, and historic architecture. Naturally, I gathered tons of recs from designers, architects, and locals (and even had the opportunity to tour historic, private estates with them!) for where to shop, eat, drink, explore, and stay in the city. With their favorite spots on your radar, you’re sure to make the most of your trip.
Where to Stay
Built upon two adjacent 19th-century homes, the Quirk Hotel is located in Charlottesville’s historic downtown—meaning plenty of restaurants, shops, and tourist attractions are only a short walk away. The property boasts a minimalist design and is packed with art, from its gallery featuring rotating exhibitions to its rooms with hand-painted headboards by local artist Kiki Slaughter. “It has fantastic concierge service, a super cool bar, and marvelous rooms,” says Madison Spencer, a Charlottesville-based architect. “You can recuperate, meet clients and friends, and exercise in as fashionable an atmosphere as you will find anywhere in Washington D.C. or Richmond.”
Keswick Hall Hotel
Look no further than Keswick Hall Hotel for a luxury retreat. The resort has it all: elegant rooms with homey touches, a golf course called Full Cry that was designed by renowned architect Pete Dye, a tennis center, restaurants, and a horizon pool with a T-shaped infinity edge for laps or lounging in a poolside cabana.
Boar’s Head Resort
Historic decor, simple furnishings, and modern amenities fill the 168 pristine guest rooms and suites at Boar’s Head Resort. During your stay, you’ll have access to the resort’s spa, tennis and pickleball facilities, restaurants, community events, and more. Not to mention, the property—owned by the University of Virginia Foundation—offers the perfect setting for morning or evening walks.
“The Boar’s Head is well situated to both downtown Charlottesville and UVA as well as outlining glorious countryside with its historic houses, vineyards, and other attractions,” designers Robert Lindgren and Thomas Gibb of Lindgren Gibb Studio share. They add: “It is a large resort-style campus with varied amenities. It lacks a sense of intimacy and the interiors are more modern as opposed to atmospheric and charming. It is very comfortable, though, and for certain purposes a perfect hotel.”
Where to Eat & Drink
Septenary Winery at Seven Oaks Farm
There’s no shortage of wineries in Virginia, and Septenary Winery at Seven Oaks Farm is worth the 15-minute drive outside of Charlottesville to Greenwood. Open to the public between Thursdays and Sundays, the family-owned, adult-only destination is situated on 109 acres of rolling hills. Go for a tasting flight, buy a picnic pack with a selection of wine and snacks, or schedule a private tour.
“All seating is full-service, whether you choose to sit on the porch, around the pool, or in the shaded grove of Magnolias (no waiting in line at a crowded bar!),” says Sarah Zimmerman, co-owner of the establishment. She also notes that the owners and staff love to share the history of the farm—which is on the National Register of Historic Places and is a registered Virginia landmark—and stories of its past owners with visitors. “We also love to educate our visitors about wine in general and specific vinification and tasting notes of our wines,” she adds.
Orzo Kitchen & Wine Bar
“I have known Ken Wooten and Charles Roumeliotes for over 20 years,” Spencer says of the c0-owners of Orzo Kitchen & Wine Bar. He continues: “Orzo is their vision of northern Italian cuisine predicated upon extensive research done in Italy over the past 20 odd years. An exceptional dining experience and very professional and knowledgeable staff–hard to come by these days–and boy do they take care of you. I often eat at the bar solo and end up meeting characters always. Full view of the kitchen and all of the action.”
Cou Cou Rachou
At bakery Cou Cou Rachou, you’ll find a fine selection of French bread and pastries that nearly look too good to eat. Among the strawberry galettes and flaky croissants, the shop also sells coffee, drinks, and merch.
Greenwood Gourmet Grocery
If you’re in need of picnic supplies, head to Greenwood Gourmet Grocery. The family-run establishment offers tons of prepared foods, ciders, wines, beers, and more. “It’s like a French village market,” Spencer gushes. “Navigate their website to order sandwiches ahead as it’s often crowded and with good reason.”
Where to Shop
Kenny Ball Antiques
Ask anyone with a bit of Charlottesville exploration expertise, and they’ll recommend going to Kenny Ball Antiques for all sorts of European treasures from art and mirrors to lighting and furniture. And if you see something you love but can’t fit in your suitcase, good news: You can get it shipped straight to your home! The shop also has a full-service design department, should you be in the market for a design consultation.
“I follow Kenny Ball on Instagram, and he does videos every day of the furniture,” says designer Linda Weisberg, who’s had the pleasure of browsing the European antiques shop. She adds: “They have beautiful traditional furniture, a lot of artwork, and accessories. The prices vary—some things are more, some things are less, so there’s something for everybody.”
Blue Whale Books
Located in Charlottesville’s Downtown Mall, Blue Whale Books offers books in practically every genre along with maps and art prints. You could spend a good hour in there, at the very least. “Unlike many musty [vintage bookshops] with random piles of books everywhere, the Blue Whale is clean and perfectly ordered—the books easy to find and archivally wrapped,” Lindgren and Gibb explain. “As to be expected, there is a strong section on Virginia, and there is no end of enjoyment in discovering titles otherwise unknown!”
The Shade Shop
The Shade Shop is truly a lampshade shade lover’s playground. From colorful, bespoke lampshades to neutral ones, this shop is sure to meet anyone’s lighting needs. Its expansive inventory also encompasses floor and table lamps, ceiling and wall lights, art, furniture, books, candles, and pillows.
“It’s very hard to get interesting lampshades, and they have a really good selection of lamps and all kinds of shades,” Weisberg gushes. She continues: “They have wicker shades. They have fabric shades. They have all kinds so that you don’t have to get a typical white lampshade. The also have a lot of decorative finials because many people are looking at lamps not just for lighting but for decoration.”
With its flagship store in Charlottesville (and a location in Paris!), Caspari acts as a go-to source for colorful tabletop essentials, stationery, and gift wrap. Many of the retailer’s pieces feature designs from renowned museums worldwide and independent artists, which vary in style. Stop by for paper plates for your next outdoor dinner party, or snag a gift like a decorative tray.
Where to Explore
University of Virginia
Envisioned by Thomas Jefferson in 1819, the University of Virginia is a must-see for history buffs and architecture admirers. “It is open to the public; gardens, buildings… all of it,” says Spencer, a UVA alum. “Stroll it with coffee in hand, chat up the students, and bring a lunch to eat on the steps of Jefferson’s Rotunda at the center of it all.”
The university even offers historical tours of the grounds for anyone who’d prefer some guidance and extra knowledge as they take it all in.
Thomas Jefferson’s Monticello
Throughout his life, Thomas Jefferson enslaved more than 600 people. At his estate, Monticello, visitors can learn about those enslaved men, women, and children who built Jefferson’s home, planted his crops, maintained his gardens, helped run his household, and raised his children. The guided outdoor walking tours focus on the experiences of those enslaved people. While many of the details of their lives went unrecorded by white historians, “decades of archaeological, documentary, and oral research helped to uncover some of the histories of those held captive at Monticello,” according to the estate’s official website.
Blue Ridge Parkway
For a dose of surreal views and a glimpse at the region’s flora and fauna, spend time at Blue Ridge Parkway. Considered America’s longest linear park, the scenic roadway stretches across 469 miles through Virginia and North Carolina. You can take a drive through it, or opt to bike or hike. Spencer recommends taking in the views while enjoying a picnic “set for a sunset or sunrise in order to charge your batteries.” If you crave even more epic views, consider going ballooning.
The Fralin Museum of Art
At the University of Virginia, The Fralin Museum of Art has nearly 14,000 wonderous objects on display. Spend an afternoon discovering the museum’s extensive art collection comprised of permanent and temporary exhibitions. The best part? Admission is free, though donations are always welcome!
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