A walk around Winchcombe soon provides you with an insight into its colourful past. En-route, you will discover several informative street signs which will tell you a little more of the local history.

Our walk around Winchcombe starts at the Town Hall (1). Built in 1853, the ground floor was formerly a Market Hall; today it houses the Tourist Information Centre, whilst on the first floor is the Winchcombe Folk and Police Museum.

Outside the Town Hall are the Old Stocks (2) which have seven holes. The whipping post also stood here, where in 1800 (according to local legend) six women were flogged "until the blood ran" for the trivial offense of hedge pulling.

Across in the High Street looking right is the Wesley House (3), where John Wesley lodged on one of his evangelical journeys. Opposite the Town Hall stands the former George Hotel (4), a famous old pilgrims' inn, built in 1490, which provided lodgings for the travelers making the pilgrimage to the abbeys of Hailes and Winchcombe. The George still retains part of the Pilgrims Gallery, which may be glimpsed through the doorway. The initials of the penultimate and famous Abbot of Winchcombe, Richard Kydderminster, are carved here on the doorway. His coat of arms can also be seen below one of the upper windows of the Abbots House (5), adjacent to the George.

Walking down the High Street into Hailes Street, we come to the Old Mint (6) on the left, reputed to have produced coins of the realm for 150 years from the time of Edgar to the reign of William Rufus (9th - 11th centuries). Mercia (7), opposite, has an overhanging first floor and traditional Cotswold stone roof. It was formerly the Sudeley Arms public house. Further down on the left Hwicci (8) was named after the local Saxon-Celtic tribe of South Mercia. Opposite again, 21 and 23 Hailes Street (9) was a Victorian Inn though the building dates back to the 16th century. Number 16 Hailes Street "Petro" (10) has an old boot scraper outside the front door. Tudor House (11) was built around 1850 and has an impressive arched gateway large enough to allow carriages into the courtyard.

The 17th century Merchant's House at 38 Hailes Street (12) is now named "The Follies". Turning left and proceeding along Chandos Street, we turn left again into Bull Lane to reach North Street, originally called Horsefair Street after the fairs that were held in March and July each year. Note the olds rings in the walls in North Street used for tethering the horses.

The Phoenix Bookshop (13), has a Phoenix Fire Insurers' wall plaque on the upper story; dating from the 18th century. 23 North Street (14) was built as the Cottage Hospital in 1888 and continued in use until 1929 when the present Winchcombe Hospital was purchased. Further along is the White Lion (15), a 15th century gabled building with stone mullion windows and an arched doorway. On the upper wall of 51 North Street (16) you can just read the old painted sign of the North Street Brewery. Opposite, the cottage at 52 North Street (17) is an in-fill of the continuation of Chandos Street to Cowl Lane, and a possible entrance to the Abbey. Built into the upper wall of 66 North Street (18) is a fine example of stone “quarried” from the Abbey. Barebones Farm (19) at 78 North Street has a bell pull with a horse shoe handle. Opposite, Treacle Mary (20) is named after Mary Yiend, who kept a sweet shop here.

According to Piggots Directory in 1847, there was in Winchcombe a “fine mineral spring, partaking of all the virtues ascribed to the Cheltenham Waters and requiring only to be known to be valuable to the town”. The Old Gate Inn (21) (now The Gate, a private house ) had a well to provide there waters, but it would appear that Spa water beer were not an acceptable combination! Through the present wrought iron gate, one can see the last tavern sign to hang here, bearing the legend “This gate hangs well and hinders none, refresh and pay and travel on”.

At the corner of North Street and Back Lane you can see a Bench Mark (22) (Broad Arrow), from the original Ordnance Survey, probably made late in the 19th century. Toll gates were in operation at every entrance to the town at the end of the 18th century, and at the Crossroads (23) stood two gates controlling the roads to Gretton and Greet.

We turn now into Back Lane, passing an Old Cider Press (24) dating from 1890 situated outside of the Library. Further along Back Lane, between the two schools, the Earthworks (25) on the left are the last remnants of the town wall from Saxon times. Retracing our steps from the Library, we turn right into Cowl Lane - the site of the Sunday morning pigmarket held in the late 19th/early 20th centuries. On our left is the Parish Hall (26).

Turning right into Abbey Terrace, we walk along to the Parish Church of St. Peters and the old Dent’s Grammar School (27). This was designed by Sir Gilbert Scott and opened in 1868. It was provided by Mrs. Dent of Sudeley.

Next door is Three Gables (28) carefully rebuilt by Emma Dent in 1882 by local stonemason John Oakley.

At 19 Gloucester Street (29) we can see one of the remaining Stable Doors with which the name Winchcombe become synonymous. During the time of the Wool Trade (13th - 15th centuries) spinning was carried out by women in the front rooms of these homes. The top half of the door was always left open so that the overseer could check that they were working. This gave rise to the saying in the surrounding area to anyone who left a door open - “Where do you come from - Winchcombe?”. Further along, we come to 23 Gloucester Street (30) which houses Winchcombe’s Railway Museum.

The Old Corner Cupboard Inn (31), on the corner of Malthouse Lane, is architecturally one of Winchcombe’s most interesting buildings. An old farm house built early in the 16th century, it was given its present name by a customer because almost every angle in the house had a corner cupboard.

Just a little further along Gloucester Street on the other side is Rabbit Box House (32). The Rabbit and Tudor Rose seen on the front wall were probably “quarried” from the Abbey.

Walking back towards town on the right hand side we reach the Old Vicarage (33), restored to its former glory in the early 1990s. We turn right into Mill Lane and follow the road around to our left. To our right now are the Chandos Almhouses (34) built in 1573 for Dorothy, Lady Chandos (of Sudeley) to house “twelve poor women of the town”. They were rebuilt in 1841, but still retain their interesting gargoyles.

Reaching Queen’s Square, immediately to our left is Jacobean House (35) built in 1618. This was Winchcombe’s first Grammar School (known as Kings School) founded for ten local boys in the name of Edward VI.

We reach Vineyard Street (36) which once led to Abbey Vineyard. Also known as Duck Street to the locals, it was the site of the old ducking stool for the “wet punishment of scolds” in the River Isbourne.

Reaching Abbey Terrace we pass the Dent’s Almhouses (37) on the right designed in a crisp Victorian style by Gilbert Scott. Abbey Terrace is built on the site of the Abbey cemetery. The original road here leading to the High Street was just 10’3” wide - so narrow that a wagon load of hay would touch the houses on one side and the Abbey wall on the other. Mop (or hiring) fairs were held here three times a year as well as “theatrical performances” (a grand name for busking). Bleby House (38) is, like many buildings here, a Georgian house on Elizabeth foundations whilst Lloyds Bank (39) was the original site of the Mercian Royal Palace. Our walking tour ends here.

To return to the starting point, walk along the High Street passing the Wesley House (3); the Town Hall is a little further along on the left hand side.