The route was a haven for bandits and highwaymen at the time, and travellers would often stop in the area rather than continue their journey at night, to avoid the high numbers of outlaws.

Much of the town's early development was attributable to the entrepreneur James Murray's decision to build his summer home, Cally House, in the area.

In 1795, Murray successfully petitioned George III to grant Gatehouse of Fleet Burgh of Barony status, further aiding development of the town.

The Public Library in the High Street was opened in 1857 and was established by Horatio Murray Stewart of Cally House, the local landowner.

Gatehouse of Fleet Town Hall, designed by James Robart Pearson, was completed in 1885 and benefits from a fine ornamental garden to its rear side.

Scenes were filmed outside the building with actors Edward Woodward as PC Howie and Britt Ekland as Willow, the landlord's daughter.

[11] Another Scheduled Monument in the Gatehouse of Fleet is Cardoness Castle, built in the late 15th century by a branch of Clan McCulloch.

It features displays on the history of the town and the Fleet Valley, a café with a riverside terrace, a second hand bookshop and the Gatehouse Tourist Information Centre.

The group of four lead the events throughout the week and hand the positions over to the newly elected at the opening ceremony of the following year's Gala.