The Rutland was originally the home of Samuel Dutton, who was Mayor of Chesterfield seven times. After his death it was purchased by John Fidler, and after enlargement and improvement it opened as The Rutland Arms. From about 1870 it became The Rutland Hotel, with many travelers and visitors occupying the seven rooms upstairs The Rutland Hotel stood on Knifesmithgate, but in 1906 its width was reduced by half to allow the road, which was renamed Stephenson Place, to be widened. The Rutland twice had a narrow escape from being destroyed by fire when the three story building across the alley way at the rear of the inn was destroyed by spectacular fires in 1900 and 1916.

The pub was bought at auction in 1921 by Tennants Brewery of Sheffield for £5350. Eventually it became a Whitbread House and traded as a Hogshead Alehouse. The original Hogshead lamps can still be seen above both main entrances. In 1923 the landlord was Joe Humphries wicket keeper for Derbyshire County Cricket Club; member of Chesterfield Cricket Club and first class cricket umpire.