The Green Man & Black's Head Royal Hotel is the most distinguished building on St John Street and has been an inn since at least the 17th century. Its overhanging gallows sign spans the entire street — a rare survival that gives the town centre much of its character. Inside, the bar retains a traditional feel without being too self-consciously preserved, and serves decent ales.
The hotel is worth a stop even if you are not staying. The bar is a good place for a post-walk pint after the Tissington Trail, and the listed building status means the original features — low beams, stone floors, Georgian fireplaces — are intact. Samuel Johnson made Ashbourne a regular stopping point on his way to visit his friend John Taylor at the Mansion House nearby, and the Green Man was where he stayed.