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.


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.

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.

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!

2023 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 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:

Charlottesville Newcomer's Guide

Welcome to Charlottesville! If you've just relocated here (or are considering it) congratulations! You won't have regrets. It combines the charm of a small college town with the cultural offerings of a much bigger city and wraps the whole package in rich history and the natural beauty of the Blue Ridge Mountains.


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


🥃 Have family in town today and want to get out of the house? Bring them out for the Thanksgiving eve “Drinksgiving” festivities this evening! We recommend the Cicchetti Bar at Tavola to enjoy a classy yet welcoming and cozy ambiance, and top notch drinks. Ask Ryan, our featured bartender for the month of November, for “dealer’s choice” if you’re unsure of what you want to order - he’ll fix you up something special! He’s been working at the Cicchetti bar for 2.5 years now, so you can put your trust in him. We tried “Ryan’s drink”, appropriately named after the man who invented it, an impressive bourbon based concoction made with Yellow Chartreuse. The bar has a full service menu, featuring some of our favorite food in town. First come first served!

🗓️ Upcoming at Tavola...
🍽️ December 4th - Seasonal dinner with chef’s tasting menu
🥂 January 31st - NYE dinner

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✨🎄🍷Experience the magic of the season at @veritaswinery this year! Veritas Illuminated is back for a second year, with a bigger and brighter display; the half mile walking trail features over 100,000 twinkling lights, and multiple new installations. We loved the new massive illuminated sleigh, perfect for photos of your crew! Cozy up by the fire with a glass of wine, mulled wine or hot cocoa in their beautifully decorated tasting room. Their new menu includes French onion grilled cheese, truffle fries and peanut butter pie. All of it was decadent, and the perfect treat to enjoy after a brisk winter walk!

🗓️ Open now through January 6th, most Thursdays-Sundays.
🎟️ Tickets range from $10-$15/person.

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✨ Introducing a brand new event this winter at Foxfield...”Balloon Glow” presented by @monticellocountryballooning, Thomas Jefferson Hot Air Ballooning, and @blueridgeballooning. December 13th, 5pm.

"A balloon glow is just what it sounds like... but better! While tethered to the ground, hot air balloons inflate and the pilots light them from within. The sight of hot air balloons lit up like giant colorful light bulbs is breathtaking. Pilots also coordinate "all burns," illuminating all balloons at once as well as "countdowns," which are very crowd participatory events."
🥘 Food trucks will be on-site at this free event! Event may be cancelled due to inclement weather. Check social media and for updates.

📸 @monticellocountryballooning

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🥘 If you're looking for a quick and healthy lunch on the downtown mall, @ottocville is an excellent choice! Otto Turkish Street Food is located on the downtown mall off of Water Street facing @ummascville, and offers delicious make your own bowls, wraps and sandwiches. Owners Ali and Haldun have been sharing their passion for extraordinary cuisine since they arrived in Charlottesville in 2013 and joined the teams of the Clifton Inn and Oakhurst Inn to fine-tune their culinary skills. Now on their own, they've enjoyed sharing the vibrant flavors of Turkish street food of their homeland in their own space - a bright and comfortable spot to dine in (on nice days they open up their garage style windows to let the sunlight and fresh air in), and convenient location to grab food for a meal at home! ...

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