48 Hours in Charlottesville: The Graduate, Wine, Shopping + Climbing

Where to Stay, Shop, Eat and Play in Charlottesville, VA

Charlottesville has been going through a tough time lately. The world has been standing right there with it as students return to the UVA campus and activists continue to stand up for what’s right. This week, Dave Matthews and his other famous friends like The Alabama Shakes, Cage the Elephant (personal fav on the bill), Justin Timberlake, Ariana Grande, and more announced a free concert. You have to request tickets here.  If you’re planning to visit for the concert or for another event in town, plan to stay a while. I’ve got a few things you should knock off the bucket list in this Charlottesville travel guide….


When I pulled up to The Graduate, I knew it would be the prefect home base for a couple days of exploration. The Graduate is located right on Main Street in Charlottesville, amidst the action of the UVA campus and in walking distance of places to eat, drink, dance, and shop. When you enter, I dare you not to play with the remote control train at the front desk!  The service staff are helpful and warm. After you check in, take time to roam around the lobby and plan our your breakfast at Sheepdog Cafe.

When you enter your room, your eyes will be drawn to a number of well placed details and designs that make the boutique hotel’s ambiance fresh, funky, yet still classic. You’ll feel like an MVP without feeling like you’re afraid you’ll break something. The rooms are spacious and the bathrooms are clean. We were obsessed with the peppermint shampoo! After you unpack, head upstairs to Heirloom for a gourmet burger if you’ve been on the road and a drink if you want to kick off a fun night on the town. The rooftop bar views are relaxing and inspiring.


From outdoor hikes to late night music, there’s something to wet every palette in Charlottesville. We kicked things off with an afternoon with Central Virginia Wine Tours. I met one of the owners, Jenny, in Richmond a few months back. I’m so glad we connected and her husband Stephen was able to drive us to some new wineries. I’ve been to a few already. See a post of my last Charlottesville winery escapades here.

As he talked about how he started his business, Stephen shuffled us to Jefferson Vineyards as our first stop. This was not my favorite wine, but this is where I got the best lesson on how to drink and enjoy wine. Then, we headed to Blenheim Vineyards, which is Dave Matthews winery. This was our favorite wine. Take my advice and just go ahead and order two bottles of the Painted Red to go. Then, off we headed to Michael Shaps Wine Works. We were in awe of the giant steel barrels located right outside of the tasting room. Finally, we ended at First Colony Winery,  which has a magical back deck and side patio for roaming around in your lightly drunken state. We grabbed a snack and stayed until they closed. FYI we passed on a visit to Trump Winery, where we saw two latin workers repairing this entryway sign.

I also recommend stopping by Pippin Hill Farms. I enjoyed a fun evening with local bloggers, my bae and Scout Bags. I try to arrange a stop here on the way in or out of Charlottesville each time I visit. It is luxurious and still one with nature. The wines and food are always a hit. This look will hit the blog soon…

Charlottesville is also full of great live music options. We stumbled upon a jazz trio at Miller’s. The food was delicious and the atmosphere felt rich and classic. It’s a local hot spot for a reason. There are music festivals, winery concerts, and underground rock and roll around town every single day. I found this comprehensive list of music in Charlottesville for your planning pleasure.

The next day, we had plans to hick Humpback Mountain. We did not make it for several reasons. But, I have big plans to hike this trail, which is just 2 miles, but offers a challenge. The view at the end is epic. Can’t you just see yourself perched at the edge for the perfect picture? It is a 30 minute drive outside of Charlottesville at mile marker 5.3. This photo from VisitCharlottesville.com is my motivation. I’m coming back for you, Charlottesville!


There are so many great places to shop in Charlottesville, many of which are located on the Downtown Mall. This time, I focused all my energy picking through Darling, a well curated consignment boutique. I went home with a few darling and also daring items I can’t wait to wear all fall. You can see a sneak in of a few of the photos in this post. I’ll be sharing those looks very soon. The owner, Linnea, got to know my style and hand selected items I loved. I saw several women come in and out of the sore who were sellers and they looked happy as they walked away if you want to make some extra cash. The boutique was recently named the best in town! Congrats!

Other shops to stop by include Bittersweet for vintage and boho new, Duo for both consignment and trendy items, Verdigris for a more sophisticated wardrobe, and the newly reopened Honey Ryder Boutique for boho staples and quality basics.


We kicked off our first morning downstairs at Sheepdog Cafe in the The Graduate. Breakfast sandwiches, parfait and killer coffee were all a great way to start the day. The second day, we ate breakfast at  Grit, one of Charlottesville’s well known breakfast joints. It has three locations depending where your adventures take you.  My crew ordered a grit bowl with bacon, eggs, cheese; a breakfast sandwich; and a MTO omelet with some bad ass chorizo. Fill up on coffee and grab snacks for your hike or your winery trip here. The chocolate granola bar we got was one of the best sweets I’ve had in a while.  Bodo’s Bagels is also a local favorite for a killer breakfast sandwich or even lunch option. I’ve cured a hangover or two with one.

If you’re on the go for lunch, Feast! Gourmet Market has locally sourced sandwiches and salads or grab a burger at Citizen Burger Bar if you  need something hardy. The Richmond restaurant is always a favorite.

Dinner spots abound. I’m not going to attempt to recommend my favorites, but on my list for this visit was Alley Light for a cool prohibition atmosphere, The Commonwealth Sky Bar for a rooftop bar experience, and Bizou for a trendy vibe. The Heirloom at The Graduate also served us well. The fries and burgers were exactly what we wanted when we ordered during our first night. Stay away from the cocktails if you don’t like sweet stuff, though. Order your liquor straight up or with soda water, if you’d like my opinion.


Thank you, Charlottesville! Until next time…

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Megan Wilson is a freelance writer and content creator based in Richmond, Virginia. As the editor of Sweet Sauce Blog, she writes about fashion, travel, self care and more.