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  • Can’t-Miss Stops to Add to Your Next Charlottesville Getaway
downtown charlottesville
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Can’t-Miss Stops to Add to Your Next Charlottesville Getaway

For a mix of luxury living and college-town cool, head to this Central Virginia destination.

By Erica Moody July 31, 2025 at 12:21 pm

Charlottesville might be best known as the home of the University of Virginia and Thomas Jefferson’s Monticello. But hop off the Amtrak at its quaint station and you’ll discover a walkable city brimming with vintage finds, farm-to-table fare, and award-winning wines. Whether you’re browsing rare books at independent shops, learning American history at area museums, or kicking back at a countryside resort, you’ll find that Charlottesville offers a versatile getaway. This story is part of our July Explore Virginia by Train issue. Check back as we share additional weekend trips in Virginia that are just a train ride away.

virginia discovery museum
Virginia Discovery Museum (Courtesy Friends of Downtown Charlottesville)

What to Do  

The train drops you off just a few blocks from the city’s brick-lined Downtown Mall, a pedestrian shopping area designed in the 1970s to revitalize the community. With its preserved historic buildings (it was added to the National Register of Historic Places last year) and more than 120 shops and 30 restaurants, it remains a gathering place for locals and a destination for visitors. Vintage style lovers will be in heaven browsing shops like Arsenic & Old Lace, where designer gowns can be found alongside breezy day dresses, polka-dot loafers, and Western staples. (It’s the real deal. Last year, actress Zendaya wore a Mugler gown sourced from the shop on the morning show Live with Kelly & Mark.) Find retro sweatshirts, denim, and records at Low Vintage and handmade slow fashion pieces at Darling x Dashing. In this literary city, you’ll find at least three independent bookstores in the Downtown Mall alone and about seven in total. New Dominion Bookshop is the oldest independent bookseller in Virginia, and the three-story Daedalus Bookshop, a Charlottesville institution since 1975, specializes in out-of-print books. More rare editions, along with antique prints and maps, can be found at Blue Whale Books.  

Walk over to the University of Virginia campus and visit its free art museums. The Fralin Museum of Art is on campus while the Kluge-Ruhe Aboriginal Art Collection is located 4.6 miles away, off of Route 250. It’s the only museum outside of Australia dedicated to Indigenous Australian art and regarded by many as one of the best of its kind in the world. The campus itself is an architectural marvel. Designed by Thomas Jefferson, it’s the only university in the world with UNESCO World Heritage Site status.  

If kids are in tow, take them to the Virginia Discovery Museum, where they can dig for fossils or pretend to be postal workers. Catch a matinee at The Paramount Theater, a restored 1930s landmark that hosts live music, comedy shows, and film series. Or stroll 10 minutes to the Jefferson School African American Heritage Center, which highlights the city’s Black history and often hosts community exhibits and cultural events. 

marigold by jean-georges
Marigold by Jean-Georges (Courtesy Keswick Hall)

Where to Dine  

Elegant yet unintimidating, Marigold by Jean-Georges at the Keswick Hall resort is well worth the 15-minute rideshare you’ll take to get to it. The seasonal, organic cuisine is as fresh as you’ll find anywhere; highlights include sashimi with spicy ponzu, crunchy maitake mushrooms, scallops, and a strawberry rhubarb dessert. The panoramic nature views from the expansive patio are equally lovely. And the wine list gives love to excellent local bottles, like Barboursville Vineyards’ Governor’s Cup–winning Vermentino.

Virginia wine can be found in downtown Charlottesville, too, at spots including Orzo Kitchen & Wine Bar, giving you a taste of the terroir if you can’t make it to the vineyards on the Monticello Wine Trail. Stop in European-style café Tilman’s for wine by the glass, charcuterie, and small plates and shop its delightful market of curated wines and accoutrements to take home with you. For Aegean/Mediterranean cuisine with a lot of flavorful plant-based options, Smyrna is a standout.  

pool at keswick hotel
Courtesy Keswick Hall

Where to Stay  

At Keswick Hall, a five-star resort in the foothills of the Blue Ridge Mountains, take a dip in its adults-only infinity-edge swimming pool that looks out over the property’s Pete Dye–designed golf course. Read a book in Crawford’s restaurant and bar while snacking on deviled eggs with Ossetra caviar. Indulge in an intuitive massage and rest in the fairytale-like relaxation lounge with panoramic woodland views at the spa.  

If you’re seeking more of a mid-range option close to downtown attractions, The Forum Hotel by Kimpton is a reliable bet. Take advantage of the bike rentals, evening social hour, and onsite arboretum and botanical garden.

Feature image courtesy Visit Charlottesville, by Sanjay Suchak

This story originally ran in our July Issue. For more stories like this, subscribe to Northern Virginia Magazine.

Erica Moody

Erica Moody

Contributing Editor

Erica Moody is Northern Virginia Magazine’s Contributing Editor. She has been a lifestyle journalist and editor for more than 15 years, with previous staff roles at Philadelphia magazine, Washington Life Magazine, and Travel Leaders Group. She’s consulted for brands including American Express Travel and Royal Caribbean. Her writing has appeared in Ad Age, The Telegraph, InsideHook, Technical.ly, DC Inno, and more. She holds an MFA from Antioch University and a BA from Tulane.

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