Virginia Wine & History Group Getaway
From historic estates to vineyard views, experience the places, stories, and landscapes that have shaped Virginia.
An Experience That Blends the Best of Both Worlds
As Virginia prepares to commemorate 250 years of American history and independence, there has never been a more meaningful time to experience the places, stories, and landscapes that have shaped Virginia. Charlottesville offers the rare opportunity to experience two of Virginia’s greatest traditions side by side: history and wine. From the vineyards of the Monticello Wine Trail to the historic landmarks that shaped early America, this thoughtfully curated group experience blends the best of both worlds for an unforgettable stay.
Your group will explore iconic historic landmarks, including Monticello, the home of Thomas Jefferson and a cornerstone of early American history, and the University of Virginia Grounds, another landmark shaped by Jefferson’s vision and architectural legacy. At Monticello, history and wine are closely intertwined, as Jefferson planted some of the first grapevines in the United States right here in Charlottesville, helping spark what we now know as American viticulture.
Already explored Monticello and UVA Grounds? Our team is here to help round out your itinerary with visits to other nearby historic destinations, including James Madison’s Montpelier and James Monroe’s Highland.
From there, continue the experience at our sister property, neighboring Pippin Hill Farm & Vineyards, where your group can experience the best of Virginia Wine Country with curated tastings, seasonal pairings, and sweeping Blue Ridge views. Guests can sip wines grown in the region where Virginia’s wine story first began.
At the heart of the package is the Founder’s Table experience, a private wine dinner hosted exclusively for your group in our historic Tavern Room. This signature dining experience features a custom menu inspired by Virginia’s terroir and farm-to-table traditions. Paired with Pippin Hill wines, the evening is designed to bring the story full circle, honoring Thomas Jefferson’s enduring belief that Virginia’s land could produce exceptional wine and food alike.
Beyond the Hill and historic sites, our concierge team can help arrange additional one-of-a-kind experiences throughout your stay. Whether your group is interested in hot air balloon rides, historic batteau excursions, or further exploring the wine trail, every itinerary is personalized to help your group experience the very best of the Blue Ridge.
Crossroads Inn is the perfect home base for the ultimate Charlottesville weekend. Our historic 1820s property surrounds guests with timeless character while offering modern comfort, inviting your group to relax, reconnect, and experience Virginia history firsthand in a place witnessed by Thomas Jefferson himself. Timed with Virginia’s 250th anniversary commemoration, the package brings together the region’s founding landmarks, celebrated wine country, and lasting traditions in one thoughtfully planned group stay.
Seamless Transportation, Thoughtfully Arranged
We are proud to partner with Monticello Wine Tour & Coach Co. to provide seamless transportation throughout your stay. Groups lodging at Crossroads Inn receive a special rate when booking with them, making it easy to explore safely and comfortably. In addition to tour transportation, their services also include airport transfers, helping create a seamless experience from arrival to departure.
Sample Itinerary for Your Group
Day One | Arrival at Crossroads Inn
Check in and settle into the Inn
Enjoy a private welcome toast
Discover the story of Crossroads Inn
Day Two | History, Wine, and Founder’s Table
Explore Monticello
Spend the afternoon at Pippin Hill Farm & Vineyards
Gather for Founder’s Table, a private wine dinner in the historic tavern
Day Three | Charlottesville and the Countryside
Tour the University of Virginia Grounds
Further explore the Virginia countryside and wine region
Depart Crossroads Inn