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.


🍻 One of our favorite views on the @monticellowinetrail is from the patio and lawn @mountidareserve. The tasting room at Mount Ida is unique in that it offers both a brewery and vineyard experience in one. And, it has its own kitchen offering a seasonal menu of shareable snacks, small plates, and larger offerings.

📅 Head out to the tasting room for Father’s Day live music June 18th 12-4pm! Reservations required.

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😍Always nice to sit back and appreciate the place you call home, especially when it is this spectacular. Thanks once again to @aerowingva for allowing us to share his stunning sunset capture from 5/17. #simplythebest #uva #charlottesville #tgif ...

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🌅 Thanks to @cartermountain for this gorgeous snap of the sun setting behind their Thursday Evening Sunset Series. Come out tomorrow for music by James 3 Duo (country, rockabilly, and blues), food by @goodwafflesco and @farmacy.cville, Carter Mountain wine, @boldrockhardcider and the best view of the sunset from anywhere around! Bring lawn chairs and blankets, or come early for a picnic table on our terrace or decks. Reserve your tickets online! Additional tickets are available at the gate only if the event is not sold out online. ...

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🎨 Our local artist feature for the month of May is someone who you may have seen around town, Randy Smith. This talented local artist, who calls himself “painter amongst people”, has been painting for over 60 years. Look for @oilpaintsmith on UVA grounds or on the downtown mall, often trying to capture the look and feel of the hustle and bustle of the crowds, with well known Charlottesville landmarks as their backdrop. You can find his works hanging in many local establishments, and purchase his paintings at @consignmenthousecville. Also, look for his prints at @finch_uva, @thevirginiashop, @awcollectables, and @revsoup. We enjoyed getting to know Randy while he worked on some recent paintings, and he was so generous to let us hang some of his work at our @charlottesvilleinsider office on the mall - come by to check it out! ...

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☀️TGIF! It should be a beautiful evening for Fridays after Five - come out and kick off the weekend with @robcva_ and @deltajunctionband at @tingpavilion!
📸 Thanks to @aerowingva for allowing us to share this cool aerial shot of the pavilion!

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🛶 The Rivanna Riverfest is happening this Saturday! Join @rivannaconservationalliance and organizing partners at @rivannarivercompany for a celebration of the Rivanna River. Enjoy fun family-friendly activities, river recreation, raffle giveaways, live performances, food, drink, and more!
May 20th 2-9pm

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🍷 Big news! Oakencroft Farm and Winery will be opening back up to the public for the first time in over 15 years, starting tomorrow! They are open by reservation only Thursday - Saturday 12-5pm. Escape the hustle and bustle of what is sure to be a crazy graduation weekend with a flight of wines paired with great snacks in a gorgeous setting!

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🥃 @virginiaspiritsexpo is putting on a tasting event @ixartpark on June 3rd! Visit with, learn about, and sample from award winning Virginia distilleries! Tickets include all-access sampling to every distillery on-site, souvenir sampling glass, and 5 voting tokens. General admission 3-8pm.
Here are the participating VA distilleries…


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🥂 We hope all you mamas out there are about to be spoiled today! Post your Mother’s Day pics to your story if you’re out and about in C-ville, and tag @charlottesvilleinsider - we’d love to reshare and celebrate you or your mama!
Thanks to @cakebloom for the cake photo. 😍

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