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.


Date Night Guide

What's better than a date night to show your love but it can also bring pressure. After all, you want a perfectly romantic evening. Here are some tips for gifts, restaurants and flowers to sweep your sweetie of his, her or their feet!

Charlottesville Holiday Guide

If you are looking for a fun and beautiful getaway for the holidays, then look no further than Charlottesville, VA. The shopping is phenomenal. The events are spectacular. And the decorations rival any big city. Join us for any or all of these events this season:

2022 Charlottesville Restaurant Guide

Not all pizza is created equal, but whether you like your crust thick and chewy, thin and crispy or somewhere in between, you'll find your idea of the perfect pie at one of these Charlottesville pizza places.

Charlottesville Wedding Guide

With breathtaking views of the Blue Ridge Mountains and rich history tracing back to the founding fathers, Charlottesville has become one of America’s top wedding destinations. Our wedding guide gives you an insider's view of Charlottesville's best wedding venues, photographers, planners, caterers, and so many more vendors.

Fall Charlottesville Guide

Summer has sundresses and sandals, but fall has tall boots and snuggly sweaters and who doesn’t love all that? Check out this round-up of Charlottesville boutiques with sweaters and other warm, comfy clothes that will help you keep the chill at bay.

Winter Survival Guide

Think outdoor dining or wine-tasting are out for the winter? Think again! Wineries and restaurants around Charlottesville know that a roaring fire does more than warm chilled fingers and toes; It creates ambience that make winter nights memorable. Here are some of our favorites.


Get the insider perspective on dining, lodging, tours and experiences from or team of local experts.


🎁✨We are so excited to host this giveaway featuring three awesome female-owned local C-ville businesses - @greenbeancville, @shopagentsinstyle, and @cscookiesoul! The winner of this giveaway will receive…

👗$50 gift card to Agents in Style consigned and new luxury and designer clothing and accessories.

🍪One dozen delicious cookies made of high quality local ingredients by Cookie Soul ($60 value).

🧸$50 gift card to Green Bean Baby Boutique, your one-stop shop for all things baby and mama, eco-friendly, organic, and sustainable.

To enter…
1) Comment on this post and tag a friend who you’d like to share your cookies with (: ✅
2) Follow @greenbeancville, @shopagentsinstyle, @cscookiesoul, and @charlottesvilleinsider ✅
3) Like this post! ✅

⏰ Our contest ends Friday 12/9 at 5pm, and a winner will be selected at random! The winner will be contacted through Instagram Direct Message for instructions on how to pick up their gifts. Thank you for participating and good luck!

*Per Instagram rules, this promotion is in no way sponsored, administered, or associated with Instagram, Inc. By entering, entrants confirm that they are 13+ years of age, release Instagram of responsibility, and agree to Instagram’s terms of use.

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🍸☕️The Peppermint Trail is calling your name! Peppermint infused cocktails and mocktails, peppermint cocoa and coffee, and even a peppermint milkshake - try them all this holiday season! Check out @friendsofcville for more info on participating businesses, for the trail map, and more “Magic on the Mall” happenings! ✨


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🎄✨🎅🏼🍻 Don’t miss Charlottesville’s Grand Illumination this Friday 5-8pm at the @tingpavilion, the event’s 25th year!
Aside from the lighting of the tree, there will be music, food, games, prizes, special guests, and plenty of holiday fun for all ages! @charlottesvillealetrail businesses will be serving up local craft beverages for the adults. Admission to the event is free! @cvillegrand

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🌲✨Get into the holiday spirit while having fun with friends, AND come home with a beautiful handmade creation of your own! Charlottesville has multiple wreath making workshops coming up at various shops and vineyards. Here are the options we found...
(Love this 📸 by! Workshop pictured instructed by @sheblooms.ciarasteinberg)

🌲@hedgefineblooms at @thebradburydowntown
Nov 30th

Dec 2nd and Dec 3rd

🌲Fifth Season
Dec 3rd

December 6th and 20th

December 7th

December 7th

December 11th

December 14th

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🦃 Happy Thanksgiving from Charlottesville Insider! We will be closing early at 1pm today, and closed Thanksgiving and Black Friday so that our staff can spend time with family. We’ll be back in the office Saturday at 9am for normal weekend hours! 🥂 ...

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✨Veritas Illuminated - experience the magic of the season at @veritaswinery with a stroll through their lighted woods and vineyard! Then head into the tasting room to get cozy near the fireplace or enjoy their outdoor firepits with wine, a new winter menu, and S’mores for the kiddos! 🍷🔥🍫
Open now until January 8th, and the illuminated walking path will be open on select Thursday, Friday, Saturday and Sunday nights throughout the season 5:15pm-8:30pm.

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🥦 Roasted Broccoli app from Oakhart Social w fish sauce caramel, sesame crumble, garlic aioli, togarashi, herbs.😋

Located in midtown Charlottesville between the downtown pedestrian mall and The University of Virginia, @oakhartsocial serves up delicious and eclectic wood-fired modern American food for sharing. Head Chef Tristan Wraight creates unique seasonal dinner menus using the best local ingredients available. And don't miss their carefully curated craft beer, wine, and cocktail lists!

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