Winchcombe immediate vicinity can be found Sudeley Castle and the remains of Hailes Abbey, which was one of the main centres of pilgrimages in Britain due to a phial possessed by the monks said to contain the Blood of Christ. There is nothing left of the now-vanished Winchcombe Abbey. St Peter's Church in the centre of the town is noted for its grotesques. The Michelin star restaurant "5 North Street" is in Winchcombe. Winchcombe sits on seven long-distance footpaths: The Cotswold Way, the Gloucestershire Way, the Wychavon Way, St Kenelm's Trail, St Kenelm's Way, the Warden's Way and the Windrush Way.
Hailes Castle the oldest constructions of its kind in Scotland. The superiority of the lands was held by the Earls of Dunbar and March. The de Gourlays, a Northumbrian family, supported the English in the Wars of Independence, and their land was forfeited by order of the Scottish Crown. Hailes Castle and lands were then confirmed upon another Northumbrian, Sir Adam de Hepburn (d. before 1371), who, in the reign of David II, had a charter of the lands of Traprain, and Southalls and Northalls (now united and called Hailes) in Haddingtonshire, as well as the lands of Mersingtoun, Cockburnspath, and Rollanstoun