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 Newhailes. The castle stands on a promontory on the Scottish River Tyne, blocking its strategic route, and preying on the route to Edinburgh. Within the 13th century curtain wall is the 14th century keep, to which ranges were added in the next two centuries. The major remaining works is the West Tower, a square donjon, which dwarfs the remains of the central tower that the Gourlays built, probably a rebuilding on the 16th century. Fifteenth century work includes a roofless chamber in which the remains of what appear to be an ambry and a piscina suggest it was a chapel