Our Historic Inn

Crossroads Inn

at Pippin Hill

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.

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OurRooms

The Pippin Cottage

Named for the neighboring vineyard, The Pippin Hill Cottage has rear views overlooking the sprawling rows of petit verdot, viognier, and sauvignon blanc grapes beneath the hills of the blue ridge. A serene, separate hideaway where the walls of history meet the windows of change.

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The Travelers Suite

From its inception, the Crossroads Inn has always been a home to weary travelers, a place to rest and recover ahead of a new day. That ethos is still the heartbeat of the Inn today.

The Roosevelt Suite

A nod to both Theodore and Franklin Roosevelt’s visits to the Inn.

Teddy Roosevelt dined at the inn after a day of birding while visiting Pine Knot, he and Edith Roosevelt’s cottage for “rest and repairs”, deep in the quiet woods of southern Albemarle County, where President Roosevelt could pursue his love of nature, wilderness and wildlife while enjoying private family time.

The Monticello Room

Named for both the home of founding father Thomas Jefferson and the dedicated wine region surrounding the Inn – The Monticello Room is an ode to the far reaches of Jefferson’s influence through his vision for Virginia wine and social change through art and architecture.

The Sutherland Room

Named for the family that built and ran the inn, Joseph Sutherland Junior first began construction on the inn in 1817 and completed in 1824 when Joseph’s son, Clifton Garland Sutherland managed the tavern and its working farm of approximately 300 acres living and working on the property along with his wife Mary, and their 16 children.

The Dabney Room

Dabney Carr was the nephew of Thomas Jefferson, married to his sister Martha. The Dabney room was the previous site of the private dining room where a meeting between Thomas Jefferson and Martin Van Buren was held in the Spring of 1823 whilst Jefferson traveled to or from Poplar Forest to be with his grandson Frances Eppes and his family.

Special Offers

20% off Your Weekday Stay

Book your weekday getaway Sunday-Thursday and receive 20% off your stay.

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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.