Things To Do
Downtown Mall
Spend an afternoon wandering the Downtown Mall, Charlottesville’s pedestrian-friendly historic district filled with restaurants, shops, coffee spots, and bars. It’s also one of the best areas to grab dinner or drinks while you’re in town. Check out Miller's for a Guinness, one of our first date spots.
Crozet
Head west toward the mountains for a little Charlottesville countryside. Stop at King Family Vineyards, explore the small town of Crozet, and grab a beer at Pro Re Nata. This makes a really fun half-day outing.
University of Virginia
Take a walk through the University of Virginia’s historic Grounds and the Lawn. Grab Bodo’s Bagels beforehand and make a picnic out of it. Explore where James and Summer first met and fell in love.
Carter Mountain Orchard and Country Store
For one of the best views overlooking Charlottesville, head up to Carter Mountain. Known for their delicious apple cider donuts and soft-serve ice cream, there is plenty of space to hang out and enjoy the view.
Humpback Rock Trailhead
For guests who want something active, Humpback Rock has one of the prettiest Blue Ridge views around. The hike is relatively short but steep, so it’s more of a workout than a leisurely walk. Go early in the morning before it gets hot in late June. Humpback is about a 40 minute drive outside of Charlottesville!
Saunders-Monticello Trail
A much more relaxed alternative to Humpback Rock. The wooded trail winds toward Monticello and is great for a morning walk without committing to a real hike. This hike was James and Summer's second official date.
Monticello
For guests who have never been to Charlottesville, Thomas Jefferson’s Monticello is great historical stop.
Eat & Drink
Breakfast: Bodo’s Bagels, Ivy Provisions, Farm Bell Kitchen, Mariebette, Tip Top Diner, The Villa Diner Lunch: Take it Away, Roots, Ivy Provisions, Lampo Takeout- IX Art Park, Brazos Tacos, The Virginian Coffee: Grit Coffee, Mariebette, Shenandoah Joe Bars: The Whiskey Jar, Fitzroy, Miller's, Coupes, The Virginian Wine: Pippin Hill, King Family Vineyards, Veritas Cider/Brewery: Potter’s Craft Cider, Devil's Backbone, Kardinal Hall Dinner: Bang, Maya, Alley Light, Tavola, C&O, Public Fish & Oyster, Tavern & Grocery, Mas Tapas Late Night Food: Christian's Pizza, Jack Brown's, Marco and Luca, Cookout