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Start your morning with breakfast at The Nook, which has been serving Charlottesville locals on The Downtown Mall since 1951. Choose from one of their Benedict selections, and don't forget to add on a Jumbo Cinnamon Roll. Sit outside on their patio so you can people watch all throughout breakfast.

Take advantage of your proximity to Virginia Wine Country and spend the day wine tasting. If you don't want to worry about driving, book a driver through Albemarle Limousine ahead of time and customize your own wine tour. We suggest starting at Keswick Vineyards for an excellent lineup of wines. Then head to Merrie Mill Farm & Vineyard, which reimagines the tasting room experience with their weird and wonderful setting, known for its uniquely maximalist style and unexpected artwork. With a full kitchen, you can also consider this your lunch spot (alongside a glass of rosé, our favorite!). Finally, end your day of wine tasting at Eastwood Farm and Winery. Don't miss their Cabernet Franc and Blanc de Blancs Governor's Cup Gold Medal winners.

Make reservations in advance to snag a coveted dinner spot at The Alley Light. Tucked away in the side streets of Charlottesville's Downtown Mall and hidden in an alley, The Alley Light offers classic French shared plates, craft cocktails, and small grower wines in a speakeasy-style setting. Their cocktail program is something you can't miss, so get there early in time for happy hour and order a Dealer's Choice with your favorite spirit. For dinner, don't miss the bone marrow and the green beans.

Keep the party going with some post-dinner cocktails at The Bebedero or dance the rest of the night away at one of Umma's famous late night dance parties (on Fridays and Saturdays). The Downtown Mall is lively well into the night, and with everything within walking distance, it's the perfect venue to keep exploring its many bars right up until bedtime.

Head downstairs to grab a pastry and coffee at Mudhouse to start off your morning on the go. Newtown Fitness is a great option for getting in a quick workout—then, it's time for some pampering.


Book a treatment at Halo Salt Spa just across the Mall. They specialize in halotherapy: an all natural, drug free, holistic therapy that is known to ease a range of common symptoms and provide a completely relaxing experience. We recommend following some relaxing time in their Salt Room with a massage.


Next, enjoy some leisurely window shopping up and down Charlottesville's Downtown Pedestrian Mall. Keep your eye out for popular consignment boutique Darling x DashingThen settle in for lunch at Citizen Burger Bar—you can never go wrong with a burger and a local beer!

On that note, why not spend the rest of your afternoon on a self-guided beer tour around Charlottesville? Start at Rockfish Brewing Company on the Mall for a pint, then walk over to South Street Brewery to visit the longest-running brewery and pub since 1998 for something on draft. Finish up by catching a car to Charlottesville's Dairy Market and enjoy a beer at Starr Hill Brewery.


While you're at the Dairy Market, grab dinner; with a foodcourt-style setup, you can snag whatever looks good, from ramen bowls and vegan burgers to Korean barbecue and soul food. Or enjoy their more elevated restaurant, Latin steakhouse South and Central followed by experimental cocktails at Milkman's Bar.

Head back to the Downtown Mall for the night: Miller's is the spot you're looking for. Residing in one of the oldest buildings on Main Street, you'll notice the apothecary display shelves and prescription drawers of the 1920s pharmacy, the old tin ceiling, and the dry ice freezer box once used for the ice cream at the soda shop—the perfect backdrop for our favorite local watering hole. Visit the infamous Third Floor for sports, cigars and billiards, and enjoy yourself well into the night.

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