My fiancé and I happen to have birthdays 4 days apart, so it’s a perfect excuse to take a long weekend trip. This year we chose to stay a bit closer to home and visit the central Virginia area. Having gone to law school in Richmond, I have been fortunate enough to spend a good amount of time in the area. Home of Thomas Jefferson’s Monticello and the prestigious University of Virginia, Charlottesville is much more than a college town. It has excellent dining, lots of history, and is an excellent jumping off point for touring Virginia wine country.

For this trip, we stayed at an AirBnb just outside Crozet, which is about 15 miles west Charlottesville. Crozet is home to the Starr Hill Brewery, as well as the iconic Crozet Pizza (chosen by the Food Network as the Best Pizza in Virginia). If you’re not feeling pizza, Crozet also has an excellent BBQ joint in Smoked Kitchen and Tap. We had dinner there our first night on a friend’s recommendation and it did not disappoint. We tried their wings, pulled pork, ribs, mac n cheese, and various sauces, but my fiancé most highly recommends their collards.
One of my personal favorite spots in Crozet, was the Bluebird and Co bookstore. As a former Scholastic Book Fair junkie, I love any opportunity to peruse a bookstore, and as Amazon continues to take over the world, those opportunities are fewer and fewer. This little gem is located right next to Crozet Pizza on the main drag, and has an excellent selection of books, local merchandise, and boutique clothing items. The staff is super friendly and more than happy to make book recommendations. I picked up a new thriller to read, and a vinyl sticker that says “Virginia is for Book Lovers,” which promptly went onto my emotional support water bottle.

When we talked about where we wanted to go for our birthday trip this year, chief among our desires was a quintessential fall experience. Being the basic b’s that we are, we love apple picking, and Carter Mountain Orchard in Batesville, Virginia is a mecca for that. The orchard grows various varieties of fruits throughout the year, so there’s almost always something for you to pick. For fall, though, you need to plan ahead a bit and purchase a timed entry ticket. Keep in mind that the ticket price is for entry only, and you have to pay for any fruit you want to pick separately. The orchards are, as advertised, on the side of a mountain, so if you have mobility issues, you may prefer their drive through apple and pumpkin pickup option.



After picking a peck of various apples, we made our way back to the barn for some fresh apple cider donuts. When I tell you these donuts were ungodly good, I truly mean it. See the photo below of me offering them up to the sun in thanks. As for the apples, we brought those home for a little baking adventure. The Bon Appetit apple pie recipe is not for the faint of heart, but it is the best apple pie I’ve ever had (and certainly the best pie I’ve ever made). There’s something about baking with the apples you yourself have picked that makes it even more special and delicious. Highly recommend.
One of the biggest draws of the greater Charlottesville area is the winery scene. This is the heart of Virginia wine country, and you have many, many options to choose from. On this trip, we only made it to Barboursville, but I have had the opportunity to visit many others in the past, so I’ve included a little list at the end of this post with some of my favorites. As a general rule, reds are typically the better Virginia varietal due to the climate, but if you’re a white drinker, there are some nice options out there as well.


On our last day, we decided to leisurely make our way back north by driving Skyline Drive in Shenandoah National Park. Our first stop, though, was breakfast at a little restaurant called Bearrr Appetit located at the Lydia Mountain Lodge and Cabins. While we just sort of stumbled upon this place on the way to where we were going, the food was good and they views were excellent. The Lodge and log cabins on site also look very nice, so it’s worth checking out if you want to stay close to the park.
October is an excellent time to visit Shenandoah not only for the temperate hiking temperatures, but also for the magnificent colors on display. Skyline Drive is a great option for getting nice views and a taste of what Shenandoah has to offer without requiring you to be super outdoorsy. There are gas stations and visitor centers dotted along the ride, so don’t worry about running out of gas or going hungry. Just try not to collide with any bears (they have signs helpfully reminding you not to do this as well).



Charlottesville Area Winery Recommendations
- Barboursville
- Tasting rooms open 10-5:00 Mon-Sat; 11-5:00 Sunday
- $25 for 6 tastes of your choice, or they have a bubbly flight and an Octagon Red flight if you’re not feeling decision-y
- Gabriele Rausse Winery
- They are only open for tastings Thurs/Fri and Sun/Mon, so plan accordingly
- I haven’t made it here just yet, but it comes highly recommended and looks like something a little different than the other wineries in the area
- Grace Estate Winery
- Open 11-5:00 Wed-Thurs, Sun; 11:00-8:30pm Fri-Sat
- Some of the best views I’ve seen from wineries in the area
- King Family Vineyards
- Open 10am-5pm daily for tastings
- Hosts Sunday polo matches, weather permitting — tailgating and food
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