Weekending: Charlottesville Edition

My family is currently plotting to escape January.

We can’t actually escape January, but every year at this time we plan a weekend trip away to shake off some of the drab ennui that accompanies this month. The weekend trip away is a very special sort of treat- everyone loves a good week-long summer vacation, but a weekend trip is a nice way to break up the routine here and there and just get away for a bit. During the Doldrums months, as I call them, when there’s very little to look forward to, we like to plan a weekend trip to get everyone excited about something, escape the monotony of inbound life in the winter, and see something new. This year’s Doldrums trip will take place either MLK Jr. weekend in January or President’s Day weekend in February, because February is pretty much the Tuesday to January’s Monday. We’re tossing around a couple possibilities at the moment but are leaning heavily toward Norfolk (so if you have any Norfolk tips, let me know!).

If you’re looking for a nice mid-winter (or anytime) escape from real life, one of our favorite Weekending destinations is Charlottesville, just about two hours away from Northern Virginia. If you’re ambitious, a 4-5 hour drive is perfectly acceptable for a weekend trip (and we have done this for a weekend trip to Pittsburgh, which we LOVED), but at 2 hours, the drive to Charlottesville is perfectly suited to the concept of a last-minute, spur of the moment, “Oh why the heck not, we have hotel points to burn”  mini vacation. You have no reason not to escape January for the weekend when somewhere so great is so close by. We’ve gone there twice now for weekend trips- once in January, once in October- and each trip we had a grand old time.

Your first stop upon reaching Charlottesville should be the Downtown Mall, which is probably one of Charlottesville’s best-loved features. A pedestrian thoroughfare that is packed with unique local restaurants, restored theaters, small shops and coffee cars, the Downtown Mall is the perfect place to get out and explore Charlottesville at the ground level. Plus your kids can’t get hit by cars. Always a plus.



Charlottesville prides itself on its local restaurant scene and there are plenty of options for lunch right on the Mall – Eppie’s for a Southern style meat-and-three platter, Citizen Burger Bar, Revolutionary Soup for a soup and sandwich plate, The Nook for old fashioned diner food, and Splendora’s for gelato are all solid choices. Java Java makes those cute little lattes with art in the foam that make you feel like a living Instagram picture.


At the far end of the Mall is Virginia Discovery Museum, a sweet little hands-on kids museum where kids can explore and play different exhibits specifically tailored to their interests- there’s a hospital, firehouse, Post Office, an Panera Bread room where they’re free to indulge in that special and fleeting childhood fantasy that work is fun. There’s also a free carousel that kids can hop on and ride. If I recall, parents have to push it to keep it going so between that and your walk up and down the Mall, you’ve successfully worked off your Java Java latte and can make room for WINE.


Charlottesville is located in the Monticello American Viticultural Area, a designated wine-making region located in Central Virginia/the Piedmont. Like Northern Virginia, there’s tons of wineries in Charlottesville producing some great Virginia wines (the Monticello Wine Trail includes 25 nearby wineries). One of our (and everyone else’s) favorites is the stunning Pippin Hill, which not only has one of the prettiest, most photogenic tasting rooms I’ve ever seen, but also incredible mountain views. The wine is great as well (their Select Red and Sauvignon blanc were our favorites).


Pippin Hill has a large grassy area overlooking the Blue Ridge Mountains and it is such a bucolic and peaceful place to sit and have a glass of wine and just… stare. When we went, a mass of kids all gathered together and organized a ragtag football game (from where they procured the football, I do not know) and I had a moment of thinking, well, if my kids aren’t going to grow up in Georgia like I did, at least they can grow up here. So they won’t be Georgia girls. To be a Virginia girl is quite an honor. Their childhood memories will be different from mine for sure, but how great will theirs be? Fond recollections of spending the waning hours of a weekend afternoon flitting in and out of vineyards.


I get to raise Virginia girls and I am not the least bit disappointed by it.



The day we were at Pippin Hill, a wedding was taking place after the tasting room closed to the public for the day and we got to watch the most gorgeous bride make her way through the grapevines to tap her groom on the shoulder so he could turn and see her in her full wedding regalia for the first time.

We’ve also visited Jefferson Vineyards, near Monticello, which was a bit more low-key than Pippin Hill (not everyone can be the Prom Queen, okay) but another great place for kids to run and play while parents sit and drink some wine. I recall their Pinot Gris being quite tasty.


While you’re over at Jefferson Vineyards, you of course need to pop into the main draw to visiting Charlottesville:


Living where we do, we’ve of course been to George Washington’s presidential home, Mount Vernon, which is no shack, but is a bit austere and ascetic compared to Jefferson’s lavish and opulent Monticello. Of course, Jefferson was like a bajillion dollars in debt when he died because although he made a salary of $25,000 a year, he had  $100,000/year salary tastes and built a house like Monticello when he really had no business building a house like Monticello, but that’s neither here nor there. This is the house that Conspicuous Consumerism built. And it’s awesome.


The tour of Monticello is probably one of the most informative, interesting tours I’ve ever taken and I’m not just saying that because I’m a huge nerd for Presidential history. The tour includes stops in Jefferson’s personal bedroom and his library still stacked with his book collection, and amusing anecdotes about items within the home, like the sitarine Jefferson’s granddaughter wanted and which he bought after her parents told her they could not afford it. (As if he could. He bought it anyway.) It feels very intimately connected to the man himself in a way the “restored to period” homes don’t necessarily match. Every aspect of Monticello was designed and planned by Jefferson himself and this is a man who is one of the great minds of all time. You can imagine the things his brain was capable of coming up with. For instance, his bed, which was built into an alcove in the wall and could be gotten into from both sides- one side was open to his library and the other was open to his personal bedroom.

If you don’t have the time or patience for a full tour, you can still explore the grounds free of charge on the Monticello Trail, which wends through woods and land surrounding Monticello.


Right up the road from Monticello is James Madison’s presidential home, Ash Lawn-Highland. I’m going to level with you: it’s no Monticello. It is a good representation of someone who exhibited modesty and fiscal responsibility. Nobody went into deep, lifelong debt for this house.

However, it’s still cool to see any home of any president (if you ask me) and this is one of the things I love about Virginia; you can’t throw a cat in this state without hitting a Presidential home. History is everywhere!


Other places and activities of note in Charlottesville:

University of Virginia, flagship university of the commonwealth. If you’re there on the right weekend you may be able to catch an athletic event (the winter schedule has a lot of swimming/diving, wrestling, and basketball on it), but if not, simply taking a walk or drive around the campus itself is impressive enough. Frankly, the school is a bit of a showboat.


Fridays After Five– From April to September, an event called Fridays After Five is held at the pavilion at the end of the Downtown Mall. Live music and local food and drink vendors are there each Friday evening, making this a fun, family-friendly event. It is also free, and attendees are welcome to bring their own picnic dinners to enjoy on the lawn.

Blenheim Vineyards– I’m singling this vineyard out in case any fans of Dave Matthews Band are reading. This vineyard is owned (and designed) by Dave Matthews himself.

Keswick Hall– A 48-room mansion, golf club, and restaurant, all in one. Take a tour of the mansion, play a round of golf, or stop in for drinks at Villa Crawford Bar and dinner at Fossett’s.


Charlottesville is one of the many, many reasons I so love my adopted home state of Virginia. Full of history, natural beauty from the Blue Ridge Mountains, exquisite architecture in Monticello and the UVA campus, local artisans, and a deep love of community that the town holds and prides itself on, Charlottesville is the kind of place that will make you want to visit again and again. We love it there and consider it one of our favorite Virginia destinations. I hope you’ll go and discover everything that’s great about it, and Virginia.

For more Charlottesville inspiration, check out the following social accounts: