Charlottesville Insider

If you’ve been to Charlottesville before, you know that it is a beautiful city filled with warm and friendly people. Incredible mountain views surround our area, but you will find amazing beauty right in the heart of the city, with colorful ‘Art in Place,’ historic architecture, peaceful trails and nature parks, and smiling faces. We are a diverse community and celebrate the uniqueness of all of our fellow citizens. If you’ve been here, you get it.

If you have not visited our lovely area, then the images and stories that you have seen or heard may have given you a different impression of what Charlottesville is all about. We want to invite you to experience the city as it truly is. Come enjoy the local wineries and breweries that are not only scenic, but are award-winning and family-friendly. Explore the downtown mall, with all of its amazing restaurants and unique shops. Take a tour of history at Monticello or Ashlawn-Highland. There are so many things to do and see.

We ask you to come support Charlottesville this August. If you look around this website, you will find many articles on things to do around the city, but we want to let you know about some great events happening during the month of August that you won’t want to miss.


The Flaming Lips – August 6, 2019 – Sprint Pavilion on the downtown mall.

Starry Nights at Veritas Vineyards – August 10, 2019 – Get your 80s clothes out of the closet and put your dancing shoes on as the Legwarmers take the stage.

Willie Nelson and Alison Krauss – August 14, 2019 – Two country legends at John Paul Jones Arena.

The Cadillac Three – August 17, 2019 – Jefferson Theater.

Gladys Knight – August 18, 2019 – Paramount Theater on the downtown mall.

Lockn’ – August 22-25, 2019 – Multi-day music festival at Oak Ridge Farm.

Dwight Yoakam – August 24, 2019 – Sprint Pavilion on the downtown mall.

Ronnie Milsap – August 31, 2019 – Paramount Theater on the downtown mall.

Ongoing in the month of August: Fridays After Five, Wine Down Wednesdays and Thursday Summer Sunset Series at Carter Mountain Orchard, various shows at the Southern Music Hall.


Annual Blackberry Harvest Festival – August 3, 2019 – Hill Top Berry Farm.

Lockn’ – August 22-25, 2019 – Multi-day music festival at Oak Ridge Farm.

Flock n Spiel Fiber Fest – August 31, 2019 – Lower Sherwood Forest – vendors, demonstrations, workshops, and door prizes.

Zaltandi – August 31, 2019 – IX Art Park – Charlottesville’s World Dance Festival.

Virginia Festival of the Wheel – August 31, 2019 – Boar’s Head Inn.

Only in Charlottesville

Voyage to Vines – August 9, 2019 – a self-guided paddling voyage to Chisholm Vineyards.

Cville Sing Out – August 10, 2019 – a great community singing event at the Sprint Pavilion on the downtown mall.

Walnut Creek Triathlon – August 24, 2019 – still time to train!

Roseland Polo – Every Sunday in August – exciting polo matches in a beautiful setting at King Family Vineyards.

Charlottesville City Market – Every Saturday in August – voted #3 Farmers Market in the nation. Opens 8am.

UVA Sports – Various August dates – Join Wahoo fans in cheering on the Men’s and Women’s Soccer teams during the month of August.

For the Kids (and Kids at Heart)

Decades Arcade – Thursdays through Sundays – all of the old arcade games you remember.

Free Family Roller Skating – every Sunday in August at Carver Rec Center.

Discovery Museum – movies, camps, and classes throughout August

Vineyards and Breweries

Area Vineyards and Breweries – while they do have year-round events, August is a happening time at area wineries and brew houses.

The rest of our website gives you many other options for your visit to Charlottesville, too. Browse around. We’re sure that you will find something that will bring you to Cville this August.

And, of course,…

If you are looking for a place to stay in Charlottesville, Stay has properties close to all of the festivities.
See a list of our properties here: or call 888-977-STAY. But whether you stay with us, with friends, or at a different location, we are excited that you are coming to visit us in Cville this August.


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