The Crossroads Inn at Pippin Hill

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.

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.

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.

Franklin Delano Roosevelt made a visit to the tavern in 1936. From the front porch of the tavern, he delivered a speech prior to dedicating the George Washington National Forest.

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.

Named for the family that built and ran the inn, Joseph Sutherland Junior first began construction on the inn in 1817 and completed in 1820 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.

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.