Matt's Winter Getaway Guide
Crossroads Inn General Manager, Matthew Lovelady, has curated the ultimate winter getaway guide to help you make the most of your weekend in Charlottesville, Virginia. From cozy bites to scenic views, this trip is all about savoring the season. And, for those seeking a blend of comfort and history, Crossroads Inn is an ideal spot for anyone looking to experience the charm of a traditional bed & breakfast while exploring the best of what Charlottesville has to offer.
Day One
Lunch at Pippin Hill Farm & Vineyards
Your winter escape has begun! Usually, I wouldn’t suggest kicking things off at the top, but in this case, Pippin Hill is a clear sign. Few things capture life's simple pleasures like a Pippin charcuterie board perfectly paired with a glass of wine. It's a gentle reminder to pause and savor the moment—especially when surrounded by the incredible landscape. Their veranda is enclosed and heated every winter, ensuring you can still take in the mountain views in cozy comfort.
Looking to dive further into Virginia’s viticulture? Try the Winter Estate Tour & Tasting for a guided exploration of six Reserve and Library selections, each paired with a bite to enhance the flavors. In my opinion, it’s the perfect way to savor Virginia wine during the winter season.
Check-In at Crossroads Inn
Our historic inn is just a stone’s throw from neighboring Pippin Hill—a quick two-minute drive. The Crossroads Innkeepers greet you with warmth and hospitality, making your comfort their top priority from the moment you arrive. Upon check-in, they’ll invite you to step back in time with a brief tour of the inn, sharing captivating stories that date back 200 years to when this historic building was known as the Crossroads Tavern. You’ll learn about its storied past, from its days as a bustling gathering spot to its transformation into the charming inn it is today. It’s the perfect way to immerse yourself in the rich history and character of this special place while settling into your stay.
Afterward, stroll across our 4-acre property to visit the chickens, explore the historic Sutherland Family Cemetery, or simply relax by the firepit while soaking in the breathtaking views of the mountains and valley.
Grab a Bite at The Alley Light
What’s cozier than a glass of wine by the fire with a loved one? At The Alley Light, a French small plates restaurant tucked away in an alley on Charlottesville’s pedestrian mall, you can do just that. Be sure to make a reservation, though, as the best cocktails in town tend to draw a crowd. And don’t forget to save room for dessert—Mr. Rech is a dreamy blend of hazelnut, praline, and chocolate you won’t want to wake up from!
Day Two
Explore Monticello
What can be said about Thomas Jefferson that hasn’t already been mentioned? Charlottesville has plenty of reasons to keep the conversation going, especially given his lasting influence on our city. From the Crossroads Inn to the University of Virginia and his home atop Monticello, Jefferson’s passion for America is still evident today. While the tour of his Monticello plantation is impressive, it also offers a sobering look at Jefferson as an individual, our country's past, and opportunities for a better future. History buffs should be sure to sign up for the ‘Behind the Scenes’ tour, which includes the recently opened third-floor dome.
Jefferson Vineyards
After touring Jefferson’s home, you can experience the fruits of his vision—vitus vinifera grown in Virginia and transformed into exceptional wines. For 40 years, Jefferson Vineyards has been making this dream a reality. I’d recommend trying their Reserve reds, but really, their entire lineup is worth exploring. You won’t be disappointed!
A Taste of Tavola
We often take for granted the simple joy of coming in from the cold to enjoy a home-cooked meal made with care. I’m reminded of this every time I pass Tavola and the flames rising from their open kitchen draw you in. The mussels are a must-order—perfect for warming you up. When the bucatini arrives, you think you’ve had enough, but one bite tells you otherwise. After this decadent meal, by the time the cold hits again, you’ll be more than ready to brave the elements.
Day Three
Carter Mountain
After enjoying a hearty breakfast from Chef Joe, you’re ready to enjoy a day exploring stunning views of Carter Mountain. One of the things I love most about the area is how green it gets in the warmer months; however, winter reveals quaint farmhouses and estates that otherwise wouldn’t be visible. From the top of Carter Mountain, you may not be picking apples in winter, but you can take in the sights of Monticello, Charlottesville, and the Piedmont. While taking a moment to sip some Virginia cider, maybe you’ll even find a hidden gem among the bare winter landscape.
The Blue Ridge Tunnel
On your way out, take a scenic drive through the Blue Ridge Tunnel. Built in the 1850s for trains traveling between Rockfish Gap and Waynesboro, the tunnel is now a nearly one-mile walking trail that connects Albemarle and Nelson counties. I can tell you, you’ll experience a unique feeling as the rock suddenly rises on both sides as you navigate your way to the tunnel entrance that lies ahead. Bring a flashlight and your walking shoes—and bundle up to stay warm!
Charlottesville is the perfect spot for a laid-back winter weekend. Whether you prefer enjoying local wine at Pippin Hill, exploring the history of Monticello, or simply relaxing at a cozy restaurant, there’s something for everyone. For those seeking a hotel or lodging in the area, we hope you’ll join us for a memorable stay at the Crossroads Inn, where you can immerse yourself in the rich historical charm of Charlottesville and enjoy our signature warm hospitality.