Not every town has unparalleled vistas, a Cab Franc made at the hands of the same person pouring it, or Dave Matthews and John Grisham walking by as you enjoy lunch at a café on its historic pedestrian mall—but Charlottesville does.

It’s urban and bucolic, historic yet modern. There are boundless hiking trails, wedding venues, wineries, breweries, boutique retail shops, and theaters (not to mention more restaurant seats than there are people to fill them). It’s for the limitless adventurer, the wine-taster, the music-seeker, and the family searching for a new experience..

At Charlottesville Insider, our goal is simple: to showcase Charlottesville by curating our ideas about what makes it unique. Follow our insiders to see what’s new, find exclusive deals, or simply figure out how to spend your day in our favorite city.



Charlottesville has wonderfully unique things to do. From horseback riding and wine tastings to pool days and historic tours. Here are our top twelve.


🍷The cooler temps today will make for a perfect outing to a local vineyard!

@eastwoodfarmandwinery has a packed schedule of Sunday fun…

Sunday, August 14th
🧘‍♀️ Mountaintop Yoga with @salutethesunyoga

💃🏼 @swingcville Dance Lesson 12:30-1:30PM
followed by
🎵 Live Music by @zuzus_hot5

🎨 Paint & Sip with @catelynkelseydesigns 3-5PM

Happy Sunday! 🥂

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🎷🥁🎺 Whether you’re a Fridays After Five regular or not, don’t miss your chance to see @elbybrass at the @tingpavilion this Friday! Virginia’s best street brass band will no doubt bring the energy and get you up on your feet and dancing!
Elby Brass hails from Fredericksburg, VA, and specializes in hard-hitting funk, sizzling soul, and shout-along favorites. Trust us, this band is so much fun! 😄

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👏 Loving this aerial capture of Charlottesville’s historic downtown mall by @aerowingva on 7/14/22!

⚡️ #summerstorms #aerialphotography

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🌮🍺 How’s this for a one-stop shop and one-two punch?! 🥊 Grab your cerveza at @rockfishbrew downtown, order directly from the kitchen @the_bebedero and have your fresh to order food brought right to your table at Rockfish!

1) Mexican Lager (Rockfish Brewing)
2) Guacamole and chips 🥑 (Bebedero)
3) Carne Asada (Bebedaro)

Happy Friday and enjoy your Friday evening in C-ville!

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🌺 Maui or Nelson County, Va?! 🌴 ...

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🌅🥂 No matter the season, you can always count on killer evening views of the Blue Ridge Mountains @knightsgambitvineyard. It’s tough to beat a glass of wine in their shaded picnic area or covered deck watching the sun set over the horse pastures at this family-owned winery in Albemarle County. Last Saturday we enjoyed live music, and food by @fireflyfoodtruck. This Saturday look for music by @maxmandu and pizza by @slice.versa to go with your wine and views! ...

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🎸🔥 Don't miss @thebaronsmusic performing live at @prorenatabrewery this Thursday! If you don't know The Barons yet, check them out in Crozet while you can! More on the Barons…

🎶 “Hailing from historic Charlottesville, Virginia in 2016, The Barons confront youthful themes of love and fear into their ethereal, booty shakin' rock n’ roll music. Fresh into their twenties, The Barons are frontman Peyton Alley, lead guitarist Josiah Ragland, bassist Kirtland Gray, and drummer Mathes Glymph. With extensive touring in the US college circuit and supporting the tours of top Billboard artists (i.e. Judah and the Lion, Catfish and the Bottlemen, Barns Courtney, The Aces, etc.) behind their back, The Barons have quickly developed their arena potential.”

”The Barons are Charlottesville, Virginia's most intriguing musical export since the Dave Matthews Band.” - Kent Romska (iHeart Radio)

@davematthewsband 🫶

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🥂🍕🎷 Tomorrow’s outing idea…Sunday Blues & Jazz at Merrie Mill Farm and Vineyard!

🎶 Paulien sings from 1-4pm: unique, dreamy…it’s a whole vibe you don’t want to miss as Dutch musician @paulienmusic will serenade you in French.

🍕 @philosopherstonepizza will be there to keep you full and happy as “Sam the pizza man” will fire up delicious pizzas in his mobile wood burning pizza oven 1-5pm.

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🧘‍♀️🍾 This Sunday head to @potterscraftcider at 10am for “Vinyasa and Views” with @flydogyoga! Get your stretch on in the morning sunshine and follow it up with a glass of Potter's cider! Sign up through Fly Dog! ...

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