Charlottesville, VA is a great city worth visiting year-round and no matter your interests. Enjoy drinking good wine and eating delicious farm to table food? It is perfect for you. Prefer to hike all day and then grab a craft beer at Starr Hill? That’s another niche this city fills. History buff? There are three presidential homes to see. The list goes on!

Of course, the only thing that can make planning a trip more fun and worthwhile is making sure you pair it with a unique experience specific to that location. Luckily, Charlottesville has great year-round events to make your trip extra special. Today I’m sharing the eight best events you won’t want to miss!

The Eight Best Charlottesville Events You Should Not Miss

Virginia Festival of the Book

Held annually every March, the Virginia Festival of the Book brings writers and readers together to promote books and literacy. The goal is to encourage discussion and inspiration by focusing on timely topics.

Events are held at the University of Virginia, on the Downtown Mall, and at other locations around Charlottesville. Most are free to attend – you don’t even need to read the book beforehand! Be sure and check out their website for the schedule of events, including some held year-round.

Tom Tom Festival

TomTom (meaning Tomorrow Tomorrow) is a festival with a very West Coast attitude aiming to do the following: connect communities around big ideas, envision the future together, and share solutions to make it happen. It’s also a big party on the Downtown Mall.

Held in April, the festival consists of pay-what-you-can conference sessions and free events like the Block Party and the Crowdfunded Pitch Party. It is also the one occasion where a section of the pedestrian mall becomes open container so you can walk around enjoying a cocktail from a local restaurant while enjoying the live music. I will warn you, there weren’t a lot of public restroom options available when I went so I would keep that in mind.

Foxfield Races

The Foxfield Races were one of the first things I learned about when I moved to Charlottesville. If you like Steeplechase Racing it’s a great opportunity for you to witness horse racing in the Charlottesville countryside. In the spring it is also a great opportunity for UVA students to over imbibe, so I recommend keeping that in mind when considering if you would rather go in April or October (though they do have designated family sections).

Tickets vary in price. If you want to do tailgating that will cost extra, but will also allow you to bring your own alcohol as long as you comply the the rules. If you opt for general admission, alcohol is available for purchase. You can learn more about rules here and ticket costs here.

Lastly, this is an event where people like to dress the part. You can expect to see dresses, shirts and ties, and even hats! The most important thing to keep in mind is you’ll be in a field outside all day, so it would not be the time to break out the stilettos.

Thursday Evening Sunset Series at Carter Mountain Orchard

From late April through September, Thursdays at Carter Mountain Orchard are a highlight in Charlottesville.

If you’ve ever visited Monticello (the home of Thomas Jefferson), you’ve probably spotted the sign for Carter Mountain. It is definitely worth a visit, even if it is only for the breathtaking views of the Blue Ridge Mountains…or their famous apple cider donuts made fresh daily.

During their Thursdays at Carter Mountain, you can expect live music, food trucks. hard cider from Bold Rock, and more while you take in the beautiful sunset. Bring your own lawn chairs and blanket for a picnic experience unlike any other. You’ll find plenty of parking in their parking lot.

Tickets can be purchased ahead of time and are $10.00/person. The event runs from 6:00 - 9:00 PM.

Crozet Arts & Crafts Festival

Occurring biannually in May and October, the Crozet Arts & Crafts Festival features items from over 120 fine artists and contemporary craft artisans. You can also expect to find delicious local food, Virginia wine and beer, live music, and more.    

Dogs on leashes are welcome and kids under 12 get in free (and check out my Guide to Dog Friendly Charlottesville here!). General admission for adults is $12.00 and proceeds go to Claudius Crozet Park, which is a non-profit community owned and operated park in Crozet (just outside of Charlottesville proper). Check out their website to purchase tickets.

Soul of C’ville

Held in August, the Soul of C’ville is a more recent event to be added to the Charlottesville scene. This three-day celebration of Black excellence is a great way to support Black owned local businesses through art, food, music, and more.

This event is also held in IX Art Park, which is located just minutes off the Downtown Mall and is a site worth visiting - especially their immersive art experience at The Looking Glass.

The festival is free and open to all to attend. Find more details here.

Charlottesville Chamber Music Festival

If you are a music lover, you won’t want to miss the Charlottesville Chamber Music Festival held in September. From several Concert Series offerings at the historic Paramount Theater and Old Cabell Hall at UVA to special events throughout the week (including a Night at the Vineyard at the lovely King Family Vineyards), you’ll be sure to find something! Most of the events are ticketed. Check out the full program here.

Winter Wander at the Boar’s Head Resort

Closing out my list, we have the event built for anyone looking to get deep into the holiday spirit.

While most people probably know Boar’s Head for its esteemed golf course Birdwood, I know it for Winter Wander. Every year the resort hosts this festive light festival surrounding the lake on their property. You can stroll the lights while drinking hot chocolate (spiked or otherwise) and then gather around a fire pit after to make s’mores. It’s holiday magic! You will feel like you are in a Hallmark Christmas movie the entire time.

I recommend checking the weather for the evening before you go. It had been unseasonably warm when my husband and I went so I was not expecting the extreme cold front that came in that evening. To say I was frozen would be an understatement! Never again will I opt for ballet flats over boots.

Charlottesville Event Calendar

There you have it - my lost of the eight events in Charlottesville you should not miss! In addition to this, there are always a ton of great things going on in Charlottesville. Be sure and follow along on my adventures to see what else there is to do! In the meantime, here is a calendar of the ones I’ve shared:

Until next time, cheers and happy exploring!