When our guests said they wished they could stay at Pippin Hill longer, we listened!

In 2022, Dean Andrews and Lynn Easton purchased The Crossroads Inn. With a passion and successful history of restoring historic inns, Dean and Lynn purchased the Inn to carry on its historic legacy through the elevated and curated Easton Porter lens.

Each room is a nod to the Easton Porter collection of properties both here in Charlottesville, Virginia as well as in Charleston, South Carolina. Our story is one that lines the walls with photos and comes through in the textures and tones of each room while preserving the incredible historic soul of the original tavern house.

So whether you are joining us for a Cooking Class, a workshop with our Horticulture team, a Vintner’s Table or even Estate Tour & Tasting, we hope you consider staying with us on the Hill a little longer at the Crossroads Inn.

Crossroads Inn veranda
Crossroads Inn Kitchen
Crossroads Patio

Speaking of Summer

Pippin Hill exterior in the summer


Virginia’s scenic views get even better in the Summertime! Join us at Crossroads, where rural charm meets authentic, historical character.

Stay with us for at least 2 nights and receive an automatic 15% off your stay.

In addition, book your 2-night stay and receive 50% off of an Estate Tour and Tasting at Pippin Hill, just a short stroll away. Enjoy a unique, in-depth exploration of our wines, vines, and garden-to-table cuisine guided by a Wine Spectator certified member of our team.*

*Stay for at least two consecutive nights and receive 15% off your stay plus 50% off of an Estate Tour and Tasting at Pippin Hill Farm and Vineyards. Blackout dates and restrictions may apply. Promotion is valid for bookings 6/11/23-8/31/23. Please reach out to the concierge to take advantage of this offer after booking.

The History

The Crossroads Inn has been accommodating travelers since it was built in 1820 and is listed on the National Historic Register as a designated Virginia Historic Landmark. Originally known as the Crossroads Tavern, the Inn served as a stop for the weary traveler. Because of the remarkable preservation and detailed rooms, the Inn can provide guests with a modern glimpse of how early 1800s taverns were built.

In the spring of 1823, a meeting between Thomas Jefferson and Martin Van Buren was held in the Dabney Carr room which was the private dining room at the time. Jefferson was either traveling to or from Poplar Forest to be with his grandson Frances Eppes and his family.

Teddy Roosevelt visited the tavern for supper following a day of birding while visiting his beloved Pine Knot.

Franklin Delano Roosevelt made a visit to the tavern in 1936 when he made a speech from the front porch prior to dedicating the George Washington National Forest.

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