The Perfect Charlottesville Weekend Itinerary: Wineries and a Cozy Inn Stay
Sometimes you just need a low-key escape to relax, recharge, and focus on wellness. I just had the perfect weekend escape and after you read this post, you will be booking one for yourself! If you’re craving a change of pace without the hassle of a long flight, Charlottesville, Virginia is one of the best weekend getaways from the DMV. Just over two hours away, this charming town offers the perfect mix of history, wine country, scenic views, and cozy accommodations—making it ideal for a quick but memorable escape.
Whether you’re planning a romantic weekend, a solo reset, or a laid-back girls’ trip, Charlottesville delivers. Here’s exactly why it should be at the top of your list—and how to plan the perfect trip.
The Perfect Charlottesville Weekend Itinerary
Why Charlottesville is a Must-Visit from the DMV
Nestled in the foothills of the Blue Ridge Mountains, Charlottesville combines small-town charm with elevated experiences. You’ll find:
Award-winning wineries
Historic landmarks
A vibrant food scene
Beautiful countryside views
And the best part? You can leave DC after work on a Friday and be sipping wine by sunset.
Where to Stay: A Charming Escape at Crossroads Inn
If you want your weekend to truly feel like an escape, skip the standard, boring hotel and book a stay at the Crossroads Inn.
This historic inn, established in 1820, is a hidden gem with just six rooms—perfect for travelers who want a quiet, intimate experience. From the moment you arrive, you feel the slower pace. The property is peaceful, surrounded by greenery, and designed for relaxation. The Crossroads Inn team hosted me for the weekend and it was just the stay I needed.
So what are the things that make this bed and breakfast so special? The rooms are cozy and thoughtfully designed rooms that feel personal rather than commercial. There are no TVs in most rooms, encouraging you to unplug and actually unwind and the atmosphere is quiet and intimate, perfect for a romantic couple’s weekend or relaxing solo stay.
Mornings here feel especially calm—think coffee, fresh air, and no rush to be anywhere. It’s the kind of place where you can truly reset, which is exactly what most of us need after a busy week in the DMV.
It’s also near wineries, historic sites, and downtown, making it the perfect base for exploring.
Things to Do in Charlottesville
If you can peel yourself away from this charming property, here are somethings you can’t miss in the area.
Step Back in Time at Monticello
No trip to Charlottesville is complete without visiting Monticello, the historic home of Thomas Jefferson and a UNESCO World Heritage Site.
Set on a hilltop with sweeping views of the surrounding countryside, Monticello offers a deeper look into early American history, architecture, and the complexities of Jefferson’s legacy. Guided tours walk you through the home and grounds, while exhibits provide important context about the lives of the enslaved people who lived and worked there.
Reservations are required for a guided tour inside the house, and they are worth it for the rich historical insight. If you don’t book a tour, you can still enjoy the stunning panoramic views and beautiful gardens and walking paths
Plan to spend at least a few hours here—it’s both educational and visually stunning.
Sip Wine with a View at Pippin Hill Farm & Vineyards
I’m never getting over Virginia wine country, and Pippin Hill Farm & Vineyards is easily one of the most picturesque wineries in the region.
The team hosted me for a gorgeous lunch and wine tasting and it was the highlight of my weekend! From the moment you arrive, you’re greeted with rolling hills, mountain views, and a beautifully designed tasting room that feels both upscale and welcoming. Enjoy a curated wine list featuring local varietals, paired with a farm-to-table food menu that pairs perfectly with your tasting. Plus the views are stunning, with one of the best sunsets you’ll see!
It’s the kind of place where you’ll want to linger—order a glass, take in the scenery, and let the afternoon stretch into evening.
Reservations for the tasting room are recommended, but you can also walk in and enjoy food and wine on the lawn. Be sure to check out their events calendar for farm-table cooking classes and crafts like floral arrangements and wreath making.
Explore Downtown Charlottesville
Downtown Charlottesville is lively but not overwhelming, making it perfect for a relaxed stroll. The historic pedestrian mall is lined with charming boutique shops, local restaurants, and coffee spots and wine bars
It’s a great place to spend a slow afternoon or grab dinner after a day of exploring. Be sure to visit Blue Whale Books for an impressive collection of rare books and world maps.
Take in the Blue Ridge Views
If you have time, take a scenic drive along the Blue Ridge Parkway or explore nearby hiking trails. Even a short drive offers incredible views, especially in the fall when the foliage is at its peak.
Just don’t do this the same day as your wine tasting!
Save the itinerary below for your trip!
The Perfect Weekend Itinerary
Friday Evening
Arrive from the DMV
Check into Crossroads Inn
Enjoy a quiet evening and unwind
Saturday
Morning: Visit Monticello
Afternoon: Wine tasting at Pippin Hill Farm & Vineyards
Evening: Dinner in downtown Charlottesville
Sunday
Slow morning at the inn
Coffee + a walk around the property
Head back to the DMV feeling recharged
Final Thoughts on Your Charlottesville Weekend Itinerary
Charlottesville is the kind of destination that feels far away without actually being far at all. It offers just enough to do without feeling rushed—and just enough quiet to help you truly reset.
From the historic beauty of Monticello to the scenic charm of Pippin Hill Farm & Vineyards, and the peaceful stay at Crossroads Inn, it’s a weekend escape that checks every box.
If you’ve been searching for an easy getaway from DC, consider this your sign.
Save this for your next weekend trip—you’ll be glad you did. And thanks again to Crossroads Inn and Pippin Hill Farm for partnering with me on this post.
