Yes, it’s been a minute since Labor Day weekend – hey, yesterday was the first day of Fall – but I couldn’t not talk about our annual family trip to Charlottesville over Labor Day. Going to Charlottesville, to technically bid summer adieu, is something Tommy and I began in 2020 simply as a means to escape the monotony of COVID and being at home + signaling the start of Fall and Kindergarten for Ava. But has now become a family tradition we hope to continue over the years.

First of all, who doesn’t love a good road trip, but also because Charlottesville isn’t too far away ( 2 hours or so driving distance), and there is so much to see and do and eat. 🙂

Here are some of the highlights of our trip.

Pippin Hill Farm & Vineyards

After countless people telling me I had to come to Pippin Hill, I finally made it here on this trip, and I’m so glad I did! First of all the property is absolutely gorgeous. How can someone not want to enter a place that has an aisle of blooming white hydrangea bushes to guide you to the entrance?

We spent two hours here, sipping delicious wine (Tommy and me) and snacking on yummy food, looking out at the beautiful Shenandoah Valley, practicing cartwheels, and just chilling.

Peach Picking at Chiles Peach Orchard and Farm Market

When I began my typical trip planning routine of reaching out to friends and colleagues for recommendations, several people told me to go peach picking if it was still in season. For some reason, it had totally escaped my mind that one peach-picks in the late summer! Not sure how this happened as I’m always on top of it for apple picking, strawberry picking, tulip picking, sunflower picking, you name it. In any event, we were able to peach pick and got some tasty peaches for ourselves and friends to enjoy for several days.

Blue Mountain Barrel House

Our friends Kathryn and Matt asked us to pick up some beer here, so naturally we had to sample a few beers and grub. 😉 Spoiler alert, we didn’t hate it, not at all.

Three Notch’d Craft Kitchen & Brewery

So good we had to come back. We stumbled upon this place last year and loved it, so it was a no-brainer we had to return back here for a meal. Nothing we have ordered here, drink or beer, has disappointed.

Farm Bell Kitchen

We ended our trip with a delicious brunch Tommy found using the Google and it was quite good!

All in all, a wonderful trip. Can’t wait to go back next year!

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