Your Local Guide to: Charlottesville, Virginia

With it's colonial style and fame of being home to three of America's founding fathers, Charlottesville Virginia is charged with historic novelties alongside Southern charm. Often characterized by its history, Charlottesville has the reputation of being intellectual and cultural, which makes it the perfect stop for any history buff.

Luxurious lifestyles are also fueled by this small gem, as Charlottesville offers abundant vineyards, polished gardens, summertime festivities, and grand estates.

So, what's going on in Charlottesville, Virginia?

What to Do 

Blackberry season starts towards the end of summer and lasts until early autumn. Finding the right place to spend the day picking blackberries is easy in Charlottesville but Hill Top Berry Farm and Winery is one of the best. Because they also produce wine, their property offers much more than just berry picking. They feature picnic areas, historic wine tours, and food pairing events. Also, make sure to stop by the gift shop for signature "True to the Fruit" goodies.

Hill Top Berry Farm and Winery

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The Ash Lawn Opera Festival is a Charlottesville staple and is currently on its 37th year! It is now at the beautifully renovated Paramount Theater presenting a wide range of performances and also educational programs for youth and adults. This festival is a cultural hub for emerging artists that should not be missed. This year the festival opens with Carlisle Floyd's melodious Susannah, and continues with Bock and Harnick's ever-popular Fiddler on the Roof

paramount theater

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Ash Lawn Opera Festival

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The Albemarle County Fair is open in July and August in Charlottesville. Famed as one of few "Old Time" county fairs, it's focus on agriculture, livestock, crafts, and music makes this an authentic Southern experience. Don't miss the opportunity to have some of the best local produce and experience historic Southern music.

Albemarle County Fair

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Monticello is now a UNESCO World Heritage Site but was once the very carefully crafted home of Thomas Jefferson. It is said that no other home quite reflects the personality of its owner like the Monticello does Jefferson. Besides it's rich history, beautiful gardens, and fascinating plantation the Monticello also offers festivals and fun activities for the kids.

The "Saturdays in the Garden" series offers exclusive natural history walks, garden lectures, and horticulture workshops. Cooking classes and workshops are among other Monticello favorites.


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The Monticello Golf Trail is features five golf courses surrounded by stunning views of the Blue Ridge Mountains, plus it is touted as one of the best sustainable golf courses in the country. Surrounded by ancient oaks, gentle streams, and hanging willows, the Monticello Golf Trail is sustainable and beautiful.

The Monticello Golf Trail

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Charlottesville's Historic Downtown Mall is one of the most beautiful pedestrian malls in the nation. With more than 120 shops and 30 different restaurants, the Historic Downtown Mall is the social center of Charlottesville. It's old building facades and red brick path evoke a sense of wonder for what the town must have been like hundreds of years ago.

The mall offers theaters, the Virginia Discover Museum, antique shops, chic boutiques, an ice rink, and a wide variety of restaurants. Plus, during the summer the mall comes alive with art installations and live music.

Charlottesville's Historic Downtown Mall

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What to Eat 

Salt Artisan Market is a market and restaurant dedicated to using locally sourced food. They are known for creating specialty sandwiches with diverse cheeses and meats. Located on Thomas Jefferson Parkway, this is a great place to grab lunch after visiting Monticello. Also, their emphasis on cheese and charcuterie makes it the perfect place to grab a pre-packaged picnic with everything made fresh to order.

Salt Artisan Market

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Fossett's is every foodie's dream. This elegant restaurant at Keswick Hall is known for serving up some of the best breakfast in the most regal of settings. A staff member at the restaurant (whom I am not allowed to cite) argues the pan-fried Virginia trout with scrambled eggs, asparagus vol-au-vent, and beurre blanc to be the best breakfast in Virginia. 


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Brookville Restaurant is the place to go for dessert! Although they do have lunch and dinner menus, funky dessert options are what make this a local favorite. From bacon chocolate chip cookies, sautéed granny smith apples a la mode, and bacon ice cream and Coke floats (yes, you read that correctly!), these desserts could not be more Southernly delicious!

Brookville Restaurant

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Where to Stay 

We must admit that our new estate, Boxwood Farm is what got us so intrigued by Charlottesville. This estate is truly spectacular and most of all, authentic. Its All-American facade welcomes guests to the 7000 square foot estate nestled in a parklike setting. Its various gardens and six acres of land are great for entertaining guests, hosting events, or even just enjoying private outdoors while on vacation.

Charlottesville Event Venues: Boxwood Farm

Because the estate has so much private land, it is the ideal location for large-scale events outdoors or even just simple ladies brunches in the garden.

Charlottesville Vacation Rentals: Boxwood Farm

The estate's interior are even more captivating than its exterior. The classic, lavish, and sophisticated style embodies the regal air running throughout the entire estate.

Charlottesville Event Rentals: Boxwood Farm

The small details are what make this estate truly beautiful. Outdoor sitting areas to sit and read a book or enjoy morning coffee are abound. One of the estate's best feature is its beautiful balcony surrounded by bountiful nature and the sound of ultimate serenity.

Charlottesville Luxury Vacation Rentals: Boxwood Farm

When considering where to throw your next event or even where to escape to for your next vacation, think Charlottesville, Virginia. Its effortless charm and historic staples make it an easy place to fall in love with. Just like us, you might be surprised by how much Charlottesville has to offer!

Your Turn... 

If you're already in love with Charlottesville, what are some of your favorite finds?