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.


🍂 Check out our Fall Guide to Charlottesville, from stores for cozy fall clothing to the best outdoor activities, and our favorite places to pick apples and pumpkins. Head to the link in our bio! ...

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🍷👏 There's no better time to visit Charlottesville's @monticellowinetrail than the present - if you haven't heard the big news, Charlottesville Virginia has been nominated for Wine Region of the Year in @wineenthusiast annual Wine Star Awards! We're just one of five regions (in the company of Lambrusco Italy, Provence France, Swartland South Africa, and Victoria Australia) nominated for this prestigious award! The winner of the Wine Star Award will be determined by the Wine Enthusiast media team and announced at the end of the month. Need a home base while you tour the area’s beautiful countryside? @staycharlottesville has you covered, including some beautiful vineyard rental properties. If you need transportation for your group, @monticellowinetour will allow you to travel in style, safely. We've added the link to the 2023 Wine Star Award Nominees to our bio. Thanks, and congrats to the many vineyards in our area who have worked so hard for this kind of distinction!
📸 @monticellowinetrail

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🍻🍷👻 Mark your calendars for the Craft Beer and Wine Fest at @mountidareserve featuring some of our very favorite local breweries and wineries!
🗓️ October 29th
🎟️ $35

🍺 Participating breweries:

🍷Participating Wineries:

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🥪 @batesvillemarket is a hidden gem, a charming historic country store in the foothills of the blue ridge mountains. Located off the @brewridgetrail and near @pippinhillfarm, @veritaswinery, @kingfamilyvineyards, @pollakvineyards, and @cardinalpoint vineyards, orchards, and the Skyline Drive, this market is a go-to for vineyard visitors, and local road bikers alike. The market features delicious sandwiches, an amazing selection of beer and wine including seasonal and hard-to-find releases at every price point, local artisan products and gift items, and weekly music and events. We stopped in and ordered one of their beers on draft, Wrench NEIPA by @industrialartsbrewing which was excellent, and enjoyed their Plank Road Turkey Pesto, which also hit the spot, at the cutest little patio table. Visit their website to learn more about their Mug Club, upcoming live music, and Oktoberfest weekend events set for Sept. 30-Oct 1! ...

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🍴The fried green tomatoes at the Aspen bar @birchandbloomcville last week were pretty special, as were their craft cocktails.🍹
👀 Insider tip - Spice up your Tuesdays at the Aspen Bar @birchandbloomcville - their talented bartenders will feature a different Sangria each week 4-10pm, creating inventive twists on this refreshing beverage featuring botanicals and seasonal fruit!

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🌮 C-ville Taco Week is coming! Monday 9/18 - Sunday 9/24 the following local restaurants will be serving $8 taco plates 🤩


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🚴🏼 The Rivanna Trail, Charlottesville’s 20 mile trail loop around the city, features a beautiful flat paved segment that runs along the Rivanna River. One of Charlottesville’s flattest terrain options, this segment is great for kids, dog walks, running and biking. Riverview Park starts the route for an out and back total of 4 miles and has parking, a playground, and river access. We started on the other side for a stop at @selvedgebrewing at the end! 🍻 Don’t miss the @rivannatrailsfoundation Loop de’Ville Fest Sept. 23-24, a celebration of the trail featuring hikes, walks, runs, bike rides and a free concert! ...

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