Charlottesville Bachelorette Weekend 2.0

So you may recall I went to Charlottesville, VA, for my sister-in-law’s bachelorette party earlier this summer. Well, I apparently cannot stay away from the city and I recently went back to Charlottesville for another bachelorette party, this time for my good friend and bride-to-be, Brooke.

While we stopped at a few of the same spots from the first bach bash in C-Ville, this bachelorette party had a much different vibe and included a few very different excursions, so it certainly deserves its own blog post!



We opted to start our weekend on a Thursday, with the majority of the group taking the day off of work to head down to Charlottesville. Our one out-of-town bridesmaid actually flew into Richmond, VA, so we picked her up on our way down from D.C., and then headed over to Charlottesville.

Instead of opting for a large rental house, this time we decided to stay at the Omni Charlottesville Hotel, which is centrally located near the downtown mall and is an ideal place to stay for easy walking access to restaurants, bars and shops.

We arranged with the hotel to have two connecting rooms, so that the group wasn’t separated during our stay, which I highly recommend!

As soon as we arrived, we began decorating our rooms with plenty of bachelorette approved banners and signs.




The bride, Brooke, also gave each of us the cutest personalized bags filled with goodies for the weekend, including wine tumblers with our monograms!



Once we were unpacked and the room was fully decorated (and our first bottle of champagne for the weekend was empty…) we changed and headed out for dinner at Red Pump Kitchen. This was a favorite of mine from the last bachelorette weekend in Charlottesville, so I knew I wanted to take this group there as well.

Since we were there on a Thursday, the restaurant was a little less crowded and our smaller group was able to sit near the open air patio. The meal was again amazing, and this spot is still #1 on my list for Charlottesville restaurants.




After dinner, we decided to go to the Commonwealth SkyBar for more drinks and catching up. Again, since it was a Thursday, the bar was almost totally empty, and we were able to sit on the patio couch and hang out for a few hours before our last weekend guest arrived and we met her back at the Omni.



Friday was our all-day wine tour day, so we knew we needed to kick off the day with an amazing brunch. We headed over to Fig Bistro (another favorite from our last Charlottesville trip) where we enjoyed $2 pint mimosas, Oreo Pancakes and a special surprise cocktail for the bride-to-be courtesy of our amazing waiter.

We then headed back to the Omni were our car for the day picked us up. We went with Blue Ridge Wine Excursions for our wine tour and could not have been more pleased with the service they provided, or our adorable driver, Gillie. Not only did Gillie pass out plenty of cold water and chocolate, but also took a group photo of us at every stop.

Stop #1 for the day was at Pippin Hill Farm & Vineyards, which was truly breathtaking. I had never been but had heard incredible things about this place, so I was so excited to finally witness it in person. The entire place is so beautiful, the views are incredible, and the wine and food is unbelievable. Overall, you must visit!




We opted for a wine tasting on their patio to begin with, and then put our names down to wait for a table outside to order some food. They take reservations for large parties, but for a small group your best bet is to get there right when they open to get one of their best tables outside.

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Since we were only a few glasses of wine in, we opted to take our photos with the bride here before heading to our next stop for the day. The backdrop was by far the best of all the wineries we went to that day, so if you’re in need of a good photo location, definitely stop at Pippin Hill!


Our next stop was to King Family Vineyards where we did another tasting and then chowed down on much needed cheese and crackers. We were able to get some amazing cheese from King Family Vineyard’s little store inside the tasting room and got a picnic table on their patio to continue our boozy day.


Last stop for our day was to Veritas Winery, which has a really incredible tasting room! This would be my top pick for a winery to visit in the winter time, with their plush couches and massive fire places.


Since we had already done two tastings, we decided to just get one bottle to split for our last hooray of the day.


After a marathon of drinking, we decided it was best to keep our momentum going, so Gillie dropped us off back at the Omni and we quickly headed back out for another drink at the Commonwealth Sky Bar while we waited for our table at Citizen Burger Bar.


The bride had been to Citizen Burger Bar before and had been dreaming about their Truffle Fries, so we immediately put in an order for those, along with their Cheese Fries to help combat all the booze we had drank that day. Needless to say, they were amazing.

We ended up spending the rest of our evening at Citizen, ordering more drinks and food until they basically kicked us out and we all realized we were way to exhausted (and drunk) to still be awake.


Our original plan for Saturday was to hang out in downtown Charlottesville, visit Kardinal Hall for brunch, possibly get our nails down and just relax. However, due to some interesting events taking place in the city that weekend, we decided it would be better to get out of the downtown area for the day.

So we pretty much woke up and headed straight back to Pippin Hill Farm & Vineyards! We arrive there before they even officially opened, but there were already groups of people there waiting to get the best seats in the house, so arriving early is clearly the secret to scoring the top table at Pippin.

We started our day with their sparkling rosé and pretty much spent the next six hours working out way through their wine and food menus.



Our favorites of the day were definitely the Pippin Sliders and the Croque Monsieur, but everything we ate was truly delicious.



We are not embarrassed to admit that we stayed at Pippin for the entire day – literally they had to kick us out because they were closing early for a wedding that evening. It was really the most wonderful and relaxing day though, spending time with amazing friends and enjoying the most beautiful scenery.


We headed back to the Omni where we spent the rest of the night ordering pizza, throwing a lingerie party for Brooke and closing down the hotel bar.



By Sunday morning, we were all pretty hurt from our boozy weekend. We were in desperate need of an amazing brunch before heading back home, and The Whiskey Jar was the answer to our prayers.

It was literally next door to the Omni, so we were able to drag our dying bodies over there without too much effort, and quickly dove into their Chicken & Waffles, BBQ Hash and their speciality, the 100% Virginia Breakfast.

Two of us brave souls decided to keep the booze train going for one more round and ordered Bloody Mary’s to close out the trip.


My second and final bachelorette trip to Charlottesville was honestly another incredible weekend and I feel like I have a special place in my heart for this city now. The food was delicious, the wine was incredible and the company was even better!

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