Bachelorette Weekend in Charlottesville, Virginia

Hello, hello and happy Tuesday, friends! Yet another weekend has gone by in a flash and before we know it, it will practically be Thanksgiving! And, yes, I know Halloween still has to happen. But, I don’t like Halloween, so until we have our own children, I kind of ignore the holiday. Tell me how you feel about it in the comments! Do you love it? Hate it? Only deal with it for your kids?

Anyways, that was totally off topic, but I feel like I start every blog post with a mini ramble, so I had to stay true to myself. Ha!

Today’s post is all about the fantastic weekend I just had celebrating my sister’s bachelorette in Charlottesville, Virginia! Now, as the “matron of honor,” I had the pleasure of planning this fun 3-day trip and you can bet it centered around food. Also, small tangent- how old does the word “matron” sound?! I was trying to convince Elli to call me the “lady of honor,” but she wouldn’t budge. In any case, I’m going to break down our days spent in Charlottesville, including the wineries we visited and the dinner restaurant you cannot miss!

If you are new to this blog, I also got married earlier this year and you can catch up on my bachelorette party here!

Friday, October 19

On Friday, we all drove to Charlottesville, Virginia to kick off Elli’s bachelorette weekend! I arrived to our Airbnb early to decorate and grab a few groceries before the rest of the girls arrived. Our Airbnb was the perfect size for the five of us to kick back and relax. It was also in the best location, with easy access to downtown Charlottesville, but also very accessible to the surrounding wineries. One downside of our stay was the actual street we stayed on… it was a bit sketchy to say the least. Sorry, mom.

Shop the “Bride” Wide-Brim Hat, the bridal sashes, or the veil!

Jefferson Vineyards

Once the other ladies arrived, we made our way to Jefferson Vineyards! After a quick 10 minute drive, we were ready for our wine tasting, a mix of 8 whites and reds. We then chose a favorite bottle and spent the afternoon in the sunshine on their patio, enjoying the cheese, baguette, and fruit I had packed for a picnic.

Mas Tapas

We then returned home to clean up for dinner, a dinner I was extremely excited for! I have mentioned this previously, but my sister studied abroad in Spain and my trip to visit her has been my favorite vacation to date. In particular, Spanish food is just my jam. Mas Tapas permanently has a wait for dinner, as they do not take reservations, but we were allowed to grab a pitcher of sangria and wait at a table on the patio.

About 30 minutes into our drinks and conversation, we were led into the cute, but quaint, restaurant. By the time our menus arrived, we were ready to feast! If you have never had tapas before, what have you been doing with your life?! Tapas are small plates, meant to be ordered in a larger quantity so you can share and try a number of dishes. This was perfect for our group and we took no time to select hummus, baked cheese and bread with jam, lamb sliders, calamari, spicy potatoes, and more!

Mas Tapas was incredible and by far my favorite restaurant of the weekend. Everything we ordered was fresh and flavorful, and perfect for sharing with a group of girls enjoying a bachelorette weekend!

Commonwealth Sky Bar

Following dinner, we hopped in an Uber and hit the downtown mall area of Charlottesville, stopping at Commonwealth Sky Bar. We planned on having this be the first stop of the night, but I think everyone was a little tired from travel and we made our way back home after a few hours.

Commonwealth has a nice environment, with open roof access and a long bar. Drink prices were as expected for a downtown bar, but the girls that ordered cocktails said they tasted great!

Saturday, October 20


Because our Friday ended on the earlier side, everyone was ready to head to breakfast early for our reservation at Fig. This brunch restaurant near University of Virginia’s campus was deserted when we arrived, mostly because it was early, but also because there was a race going on in downtown Charlottesville, which made it very hard to actually get there! Once situated, we all enjoyed a great breakfast. I ordered the chicken and waffles, which is my go-to when I want a meal that is sweet, but will also keep me full. A number of the girls ordered the special, avocado toast, which they also reported liking!

Pippin Hill Farm and Vineyards

After breakfast, we wandered “The Corner” for a bit before heading for Pippin Hill! I had read on a few blogs that we should aim to be at the winery as close to opening as possible, because it is very popular and fills up fast. We arrived about 10 minutes after the 11am opening to a very full parking lot! Luckily, we were able to head in for a tasting immediately.

Shop our custom shirts here!
If you have a sister and don’t have a picture like this, are you even sisters?

Now, this site is breathtaking! It was overcast while we were there, but I can only imagine how it would have looked in clearer weather. It is surrounded by mountains and the architecture is the perfect mix of farmhouse and modern. They were actually setting up for a wedding that evening, which I bet was gorgeous!

We walked the property with wine glasses in hand, strolling around their vegetable gardens, peeking in on the chickens, and meandering around the vines. Pippin Hill does have a full kitchen and the food looked great, however we were all still full from breakfast.

The main reason we decided to visit this winery, outside of the reviews, was that Elli’s future last name is Pippin! Isn’t that so fun? We made her pose with the sign on the way out. Ha!

Blue Mountain Brewery

Next stop was Blue Mountain Brewery, for a change in alcohol and a round of appetizers for lunch! The brewery was about a 20 minute drive from Pippin, on winding country roads.

The other four girls all ordered flights of beer, while I ordered a lemonade shandy because #designateddriver. The food was delicious and again, you cannot go wrong with the views in this area of Virginia. I told Jarrett that driving into Charlottesville made me instantly happier. I miss the mountains in New England so much, so being surrounded by these was a blessing.

Veritas Winery

Our day-drinking tour ended at Veritas! You can probably guess that we began with a tasting, followed by splitting a bottle or two and hanging out of the expansive deck. We really lucked out with the weather, with temps in the 50s and 60s, but no rain!

Veritas was extra-special because they were hosting a wedding! The wedding party was taking pictures throughout the property and the bride was gorgeous! I think it made it all the more fun that we were celebrating our own bride-to-be, while witnessing someone’s special day.

Citizen Burger Bar

Dinner was at Citizen Burger Bar, which is located on the downtown mall in Charlottesville. Honestly, it was good, but not amazing. I do have to rave about the truffle fries, but the burger was just okay. They do offer a vegan burger, which one of the girls ordered and enjoyed.

Jarrett and I had been here on a previous trip and from what I recall, the food was better back then. Maybe it was just an off night?

The night again ended early, when Elli announced that all she really wanted was to get in bed and watch a movie. That sounded like heaven to me, being the old lady surrounded by 23 year olds. Ha! I think the day of drinking really took it out of everyone.

Sunday, October 21

Bodo’s Bagels

On Sunday, we all awoke feeling refreshed and ready to finish the weekend with a lot of carbs! Once we checked out of our Airbnb, we made our way towards one of the locations of Bodo’s Bagels. Guys, the line was crazy! It moved quickly, but it was nuts. Good thing these really are some of the best bagels.

I had a cinnamon raisin bagel with cream cheese, while others opted for heartier egg sandwiches.

Carter’s Mountain Orchard

The final stop of the bachelorette weekend was Carter’s Mountain, for apple cider donuts and a few more breathtaking mountain views. To get to Carter’s Mountain, you have to scale this incredibly windy, steep road so four-wheel drive helps! It is paved, but definitely not for the faint of heart.

After we arrived, we were shuttled to various parking areas and embarked on the busiest apple orchard I have ever seen. There had to have been thousands of people there, plus it was a blustery 50 degrees with wind! So, while our time there was not as leisurely as originally intended, we all enjoyed fresh apple cider donuts before saying goodbye to the bride!

I had such a fun weekend celebrating my sister during her bachelorette weekend! Now, onto finalizing her bridal shower 🙂

Questions? Comments? Words of Advice?

This site uses Akismet to reduce spam. Learn how your comment data is processed.