The Perfect Fall 🍁 Getaway to Charlottesville & the Blue Ridge Mountains⛰️🍂

If you're looking for the ultimate fall getaway in Virginia, this two-day road trip has pretty much everything I want in an October adventure: mountain views, apple cider, pumpkin picking, historic stops, cozy coffee shops, incredible food, Virginia wine, whisky and one of the prettiest waterfalls in the state.

Here's how I'd spend two perfect fall days in this part of Virginia!

DAY 1: Charlottesville + Carter Mountain + Pippin Hill

Carter Mountain Orchard

Carter Mountain Orchard is one of my favorite classic fall stops near Charlottesville. Sitting high above the surrounding countryside, the views alone make this worth visiting.

Grab an apple cider slushie, pick up some apples and take a minute to soak in those Blue Ridge views.

Fair warning: October is prime Carter Mountain season, so expect it to be popular (especially weekends!). You need tickets on the weekends.

Lunch at Botanical Fare

Head back into Charlottesville for lunch at Botanical Plant-Based Fare, a completely plant-based restaurant with colorful bowls, salads and other feel-good comfort food.

Coffee at Lone Light Coffee

After lunch, make a quick stop at Lone Light Coffee for your afternoon caffeine fix before heading out into Virginia wine country.

Chiles Peach Orchard

Head about 20 minutes west to Chiles Peach Orchard for pumpkin picking and more beautiful mountain scenery.

Pippin Hill Farm & Vineyards

Make a tasting room reservation at Pippin Hill Farm & Vineyards, one of the most beautiful wineries in Virginia.

The property overlooks rolling vineyards and the Blue Ridge Mountains, and in October? It's fantastic!

Give yourself plenty of time to enjoy the views, order a wine tasting and try some of their food. Pippin Hill focuses heavily on locally sourced ingredients, including produce grown right on the property.

Check Into The Crossroads Inn

The best part? We're staying right on the Pippin Hill property at The Crossroads Inn!

This historic country inn dates back to 1820 and sits just down the hill from the vineyard, making it the PERFECT place to turn an afternoon at Pippin Hill into a cozy Virginia fall getaway.

After checking in, take some time to explore the inn and property before settling in for the evening. After a full day of historic sites, apple cider, mountain views and Virginia wine, we're keeping dinner simple and eating in our room.

Honestly, this is exactly how I want to end a fall day in Virginia.

DAY 2: Pumpkins, Virginia Whisky + Waterfalls

Breakfast at the Hotel

Crossroads Inn comes with breakfast, so make sure to let them know ahead of time if you have any dietary restrictions. They made us avocado toast.

Then it's time for another gorgeous fall drive through Central Virginia.

Crabtree Falls

Next up: one of Virginia's most spectacular waterfalls.

Crabtree Falls is a series of cascading waterfalls in Nelson County and is often considered one of the tallest waterfall systems east of the Mississippi.

You can make this as short or as adventurous as you'd like. Even if you don't tackle the entire trail, you can still see beautiful waterfall views relatively early in the hike.

And surrounded by October foliage? YES PLEASE.

Virginia Distillery Co.

Drive approximately 30 minutes to Virginia Distillery Co.

This gorgeous distillery specializes in American single malt whisky and is tucked into the foothills of the Blue Ridge Mountains. Take a tour, do a tasting or simply enjoy the property.

From here, it's roughly a one and a half hour drive back to Richmond.

*Have More Time? Add These Stops!

There are WAY too many good stops in this area to squeeze into one weekend, so if you're staying longer or want to build your own version of this itinerary, add these to your list:

The Yellow Mug in Crozet is a cute local coffee stop that's perfect if your route takes you through town.

Blue Ridge Tunnel is one of the coolest hikes in the area. You can literally walk through a historic railroad tunnel underneath Afton Mountain, so bring a flashlight!

Loving Cup Vineyard & Winery is another option for wine lovers and is especially interesting because it's an organic vineyard.

Albemarle CiderWorks is basically made for a fall Virginia itinerary. Their specialty is Virginia hard cider, and the beautiful property is surrounded by orchards and countryside.

Looking for even more fall adventures? Check out my other Virginia fall guides for pumpkin patches, apple orchards, scenic drives, hikes, festivals and more of my favorite ways to experience fall in Virginia - click here. I hope you found this itinerary helpful! There are more blogs on my website about other spots around Virginia, as well as Richmond tips. You can also follow me on YouTube for my travel videos or Instagram for daily updates. Feel free to DM me with any questions! Have a great trip!

💚Lauren Z Ray