Travel Guide: A Weekend Getaway with the Graduate Charlottesville

Charlottesville is a place that’s near and dear to my heart. I went to school there, lived there for a year after I graduated, and I try to get back to C’ville for at least one or two football games and another trip in the spring every year. Despite the news recently, it’s a lovely, liberal, artsy, diverse enclave nestled in the Blue Ridge Mountains, and I was delighted to spend a summer weekend wine tasting, dining, and staying with the Graduate Charlottesville last month. There is no better place on earth to plan a weekend getaway.


Of course the activities in Charlottesville are plentiful; you can go hiking, explore history, check out awesome concert venues, go shopping on the Downtown Mall. But, my preferred way to spend an afternoon in C’ville is wine tasting. You can’t beat the mountain view backdrop in Albemarle County, and aren’t those best appreciated with a glass of rosé?

We actually decided to switch things up a bit on this trip by starting out at Castle Hill Cider, which i actually found to be a more refreshing option on a warm, slightly humid day. With a local cheese and charcuterie plate to accompany our wine flights, we had the perfect afternoon snack. I left with a bottle of cider that carried strong notes of rosemary (doesn’t that sound sophisticated?).

From Castle Hill, we headed to nearby Keswick Vineyards, which has a homey, local feel. The views are wooded rather than sweeping fields, and you get the feeling the visitors relaxing with their wine and dogs on the front porch have been there more than a few times. Keswick is open later than the other vineyards, and you’ll certainly want to stay a while. We opted for glasses rather than a tasting and took our time lounging outside.




I’ve dined all over Charlottesville and have a whole slew of recommendations from casual spots that have been long time favorites to finer dining occasions to places that seem quintessentially “Charlottesville.” None, however, can compete with the view at Heirloom Rooftop + Bar which sits atop the Graduate Charlottesville. With sweeping views of the city nestled below the Blue Ridge Mountains, it’s an escape above the bustle of Main Street below.

We started off the evening with cocktails  — the Southern for me, and the Moonflower for Adam. The wine selection features several Virginia vineyards, but we stuck to the cocktails. I couldn’t turn down a combination of whiskey and peach. We then ordered a variety of small plates, each one better than the last. I even discovered that I kind of enjoy pork rinds…always learning something new. And don’t miss the Pork Loin Sliders or the Mixed Green & Grilled Shrimp — the local chevre from Caromont Farm in the salad was to die for. I can never turn down a dessert menu, so dinner ended with a jar full of banana pudding, which was devoured down to the very last crumb.




The next morning, we walked downstairs at the Graduate Charlottesville to the Sheepdog Cafe, a bustling little spot that it as convenient for guests staying at the hotel as it is for those just strolling down the street. While this particular morning they unfortunately did not have any of the little donuts they’re known for, they did have biscuit breakfast sandwiches and an array of coffee, lattes, and teas. The cafe also offers lunch, dinner, and drinks.




Back when I was at U.Va., the only hotel on the Corner, which is prime real estate, was the Red Roof Inn. I never stepped foot in the place, but I heard it was bare bones to say the least, relying on its location to book rooms. Now, that same location has been turned into the Graduate Charlottesville, a hotel that would be worth visiting even without its standout spot.
The ambiance strikes a chord that is old school, collegiate, and modern all at the same time. Gallery walls full of vintage portraits, Charlottesville throwbacks, and gilded frames next to sumptuous velvets and retro tartans. The Graduate Charlottesville is spot on with its decor. Throw in the unbelievable location, friendly staff, and two yummy restaurants, and you can bet I’ll be back.




Thank you to the Graduate Charlottesville, Heirloom Rooftop + Bar, and Sheepdog Cafe for hosting me in Charlottesville. As always, all opinions, photographs, and thoughts are my own.


Leave a Reply