Easily reached by the farm’s network of walking trails, Lone Tree Hill is the farm’s highest point. From here you can see spectacular views of Lake Champlain and the Adirondacks to the west, and of the Green Mountains to the east. A memorial to Derick V. Webb, who donated the lands and buildings of Shelburne Farms to the nonprofit organization, is also located near this beautiful height of land. Much of the agricultural land visible from Lone Tree Hill is permanently protected by conservation easements.

According to the original plans for this turn-of-the-century agricultural estate, a grand mansion was to be built at the top of Lone Tree Hill, replacing the temporary "cottage" sitting on its lake-side bluff. Instead, the estate founders Lila and William Seward Webb focused their energies on modifying the 1887 cottage. Today, that cottage is The Inn at Shelburne Farms, while Lone Tree Hill remains the domain of walkers.