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sunset walk on the downtowm mall
Explore the Best Scenic Drives Near Charlottesville
Explore the beauty of Central Virginia through iconic scenic drives like the Blue Ridge Parkway and Skyline Drive.
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sunset walk on the downtowm mall
Holiday Light Tours with Monticello Wine Tours
Relax and enjoy the season on a curated route, including the Richmond Tacky Light Tour or our Veritas & Flying Fox Christmas Tour.
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sunset walk on the downtowm mall
Why Charlottesville is the Best Weekend Getaway from DC
Charlottesville, located approximately 120 miles southwest of Washington DC, is easily accessible by car, train, or bus.
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sunset walk on the downtowm mall
Discover Charlottesville Hotels
Discover accommodations that seamlessly blend historic charm with modern luxury, redefining comfort and hospitality.
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sunset walk on the downtowm mall
Holiday Fun in Charlottesville
Explore festive Christmas lights, visit Monticello, ice skate, shop at holiday markets, and enjoy winery events.
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Charlottesville Insider: Your Guide to Wineries, Hotels, Events, and More!

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 what to do in 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.

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Make Your Stay in Charlottesville Unique

Planning a weekend getaway or extended stay? Book a property from our curated collection of vacation rentals to experience a true taste of Charlottesville's charm. Each property on our list is handpicked for its character and proximity to Charlottesville's top attractions.

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🥪🏀 We wanted to spotlight the “Ty Jerome” sammie special at @ivyprovisions - chicken, grilled peppers and onions, melted American cheese, tomato, green goddess, spicy mayo, lettuce, served on a fresh baguette. Named after the former UVA basketball star turned Pro, and member of the 2019 National Championship team, $1 from each Ty purchase goes to benefit the UVA Children’s Hospital!  Why Ty?  A fan of Ivy Provisions, he reached out to the sandwich shop, then came in and collaborated with the kitchen to create his ultimate sandwich!  @uvamenshoops opens their season this evening at JPJ against Campbell!  #gohoos 🔶🔷

🥪🏀 We wanted to spotlight the “Ty Jerome” sammie special at @ivyprovisions - chicken, grilled peppers and onions, melted American cheese, tomato, green goddess, spicy mayo, lettuce, served on a fresh baguette. Named after the former UVA basketball star turned Pro, and member of the 2019 National Championship team, $1 from each Ty purchase goes to benefit the UVA Children’s Hospital! Why Ty? A fan of Ivy Provisions, he reached out to the sandwich shop, then came in and collaborated with the kitchen to create his ultimate sandwich! @uvamenshoops opens their season this evening at JPJ against Campbell! #gohoos 🔶🔷 ...

✨Charlottesville is a magical place to spend the holiday season. With twinkling lights, festive events, holiday shopping, and seasonal attractions, you’ll find your holiday spirit!  From ice skating to visiting historic Monticello, Charlottesville provides a variety of winter activities that create a perfect holiday experience. We’ve handpicked a list of seasonal attractions you won’t want to miss in 2024!  From special events, to Christmas light tours, where to buy your Christmas tree, and festive winery and brewery events, we have you covered for holiday fun! 🔗 Link to the Holiday Fun Guide in our profile.

✨Charlottesville is a magical place to spend the holiday season. With twinkling lights, festive events, holiday shopping, and seasonal attractions, you’ll find your holiday spirit! From ice skating to visiting historic Monticello, Charlottesville provides a variety of winter activities that create a perfect holiday experience. We’ve handpicked a list of seasonal attractions you won’t want to miss in 2024! From special events, to Christmas light tours, where to buy your Christmas tree, and festive winery and brewery events, we have you covered for holiday fun! 🔗 Link to the Holiday Fun Guide in our profile. ...

Fall magic at Keswick Hall 🍁🍂✨

We had the privilege of exploring every corner of #KeswickHall, and it’s truly a fall destination like no other! A special thank you to @keswick_hall for the insider’s look at everything from world-class dining to ultimate relaxation.

Virginia in the fall doesn’t get any better than this!

#keswickhall #keswickva #luxuryhotel #vahotel #spa #keswickgolfclub #golf #golfclub #charlottesvilleinsider #charlottesville #charlottesvilleva #marigoldkeswick #

Fall magic at Keswick Hall 🍁🍂✨

We had the privilege of exploring every corner of #KeswickHall, and it’s truly a fall destination like no other! A special thank you to @keswick_hall for the insider’s look at everything from world-class dining to ultimate relaxation.

Virginia in the fall doesn’t get any better than this!

#keswickhall #keswickva #luxuryhotel #vahotel #spa #keswickgolfclub #golf #golfclub #charlottesvilleinsider #charlottesville #charlottesvilleva #marigoldkeswick #
...

🎃✨Happy Halloween!  The @uva Rotunda is transforming into something spooky - from dancing skeletons to haunting pumpkins and enchanted cauldrons, the work of @zilog80_visual_art uses one of Charlottesville’s most iconic sites to create an eerie, mesmerizing experience. 
🗓️ Visit “The Great Rotumpkin” from Oct 31 - Nov 2, 7-11 PM – it’s free, open to the public, and an absolute must-see! 🧟👺👻

🎃✨Happy Halloween! The @uva Rotunda is transforming into something spooky - from dancing skeletons to haunting pumpkins and enchanted cauldrons, the work of @zilog80_visual_art uses one of Charlottesville’s most iconic sites to create an eerie, mesmerizing experience.
🗓️ Visit “The Great Rotumpkin” from Oct 31 - Nov 2, 7-11 PM – it’s free, open to the public, and an absolute must-see! 🧟👺👻
...

🍂🍻 Our Insider Featured Event for this week is the @the_wool_factory 4th Annual Fall Fest, a gathering created to enjoy the finest Virginia weather and indulge in exceptional local food and beverages!  Live music, kids activities, and FREE admission.  Featuring beers from @selvedgebrewing and Virginia wines curated by @theworkshop_cville. Sunday, November 3rd 12-5pm. 

🗓️ Would you like our hand picked list of events sent to your inbox once per week?  Sign up to receive our email newsletter at the link in our profile.

🍂🍻 Our Insider Featured Event for this week is the @the_wool_factory 4th Annual Fall Fest, a gathering created to enjoy the finest Virginia weather and indulge in exceptional local food and beverages! Live music, kids activities, and FREE admission. Featuring beers from @selvedgebrewing and Virginia wines curated by @theworkshop_cville. Sunday, November 3rd 12-5pm.

🗓️ Would you like our hand picked list of events sent to your inbox once per week? Sign up to receive our email newsletter at the link in our profile.
...

🤩 Hello weekend!  If you’re looking for something fun to get into, head to the link in our bio to browse our event listings. 

🎵This evening downtown:

Whiskey Myers
@tingpavilion 
7pm

Mock Star’s Ball 2024
@southerncville 
8pm

Waynesboro Symphony Orchestra
@theparamounttheater 
7:30pm

🤩 Hello weekend! If you’re looking for something fun to get into, head to the link in our bio to browse our event listings.

🎵This evening downtown:

Whiskey Myers
@tingpavilion
7pm

Mock Star’s Ball 2024
@southerncville
8pm

Waynesboro Symphony Orchestra
@theparamounttheater
7:30pm
...