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 truces with England in 1449, 1451-7 and 1459. It is thought that Sir Patrick Hepburn dramatically extended the castle. A massive tower of at least four storeys was built to the west of the original construction, and a lower tower to the East to form a long north range, looming above the River Tyne. The thick curtain wall of the castle may date back to the 13th century. In 1400 it successfully withstood an attack from Harry Hotspur Percy, in league with the Earl of March. The attackers were defeated afterwards in a counter-attack led by Archibald, Master of Douglas.