(1) Start outside the Almshouse of St. John on Trendle Street. In front of you is the Almshouse of St. John the Baptist and St. John the Evangelist. It was built in 1437‒1438 to house 17 poor men and women. The residents received full board, lodging and clothing, in return for surrendering their possessions on entry and agreeing to abide by the administrative and religious rules of the house. The Almshouse continues to care for the elderly today and is open to the public in the summer months.

(2) Walk up to the Abbey Church. The Abbey Church is mainly 15th century and has the heaviest peal of 8 bells in the world. The most beautiful feature is the stone, fan-vaulted ceiling, definitely worth a closer look. The Great West Window was replaced and dedicated in the presence of Her Majesty The Queen in 1998. Detailed information about the Abbey is available inside. The Digby Memorial standing in front of the Abbey was erected in 1884 to commemorate the life of George Wingfield Digby, a benefactor of the Victorian restoration of the Abbey.

(3) Facing the Abbey, walk to the far right of the building and spot the 18th century sundial. Continue past the sundial, enter Church Lane and walk towards the Bow Arch. On your right you will find the Sherborne Museum which presents the townʼs history, as far back as Roman times. Its exhibitions are always changing and it is well worth a visit. Here you will find the model of Sherborne Old Castle before it was besieged and a digital version of the Sherborne Missal on loan from the British Library.

(4) Walk further along Church Lane and you will arrive at The Bow Arch. The Arch is 15th century and provides a gateway between commercial Sherborne and the Abbey precincts. It is believed that 12 Monmouth rebels from the local area were hanged here in 1685.

(5) Walk beneath the Bow Arch and onto the Parade, where the regular markets are held. Directly in front of you is the Conduit. This was the monkʼs lavatorium or washhouse originally sited within the cloisters c.1512. It was moved here after 1539 following the dissolution of the monastery. It has since been used as a water supply, a police station, a bank and a reading room.

(6) Turn left, and head up Cheap Street. On your right opposite the Conduit, is the Abbey Pharmacy, a beautifully restored building dating from 1790. Number 73, a little further along, is 18/19th century and has a beautiful plaster ceiling depicting the Four Seasons, which you may be able to view. Further along on your left, a 16th century, half-timbered house called Abbeylands can be seen.Opposite is Swan Yard, a small walk-through shopping complex converted from stables.

(7) As you reach the top of Cheap Street, you will see The Julian, beside a half timbered building, on your right. The Julian itself was also originally half timbered and was the early 16th century hospice of St. Julian of Norwich.

(8) Next door to the Julian is The George. The George was built on the site of an earlier inn, and is 16th century. It is Sherborneʼs oldest surviving inn. Note the Tudor archway alongside.

(9) Bearing left at the top of Cheap Street you will find The Green on your left. This was built for a wealthy clothier and is the best preserved 17th century merchantʼs house in Sherborne.

(10) Return back to the Julian. Facing back down Cheap Street, take the next left turn into Newland. On your left you will see The Manor House. This is a much altered 15th/16th century building. The most important point of interest is the late mediaeval oriel window. This building is now owned by Sherborne Town Council.

(11) Continue along Newland. On the right hand side you will find the Paddock Gardens, a walled refuge and great spot to sit and relax.

(12) Turn around and retrace your steps, back through Cheap Street. About halfway down, turn right and follow the road to see the great court of Sherborne School. (Private grounds.) This is one of the great public schools of England. It was re-founded in 1550 by King Edward VI and incorporates some of the monastic buildings. 650 boys attend the school today compared with only 40 in 1850. Several major films including The Guinea Pig (1948), Goodbye Mr Chips (1969), and The Browning Version (1994) were filmed here, and more recently The Imitation Game and the BBCʼs historical TV drama Wolf Hall.

(13) Return to Cheap Street. Further down, on your right, tucked away behind the main shopping street you will glimpse Cheap Street Church - worth a peek inside.

(14) Continue down Cheap Street past the Conduit and follow the road into Half Moon Street. On your right is Church House Gallery built in 1532 as a Church House, with a row of shops below and one long room, the Parish Hall (with its identical windows), on the first floor. The Queenʼs Majestiesʻ players performed here in 1587, to an audience which perhaps included Sir Walter and Lady Raleigh.

(15) Cross the road and turn right into South Street. After about 200 metres you will reach Pageant Gardens, on your right. The Gardens were funded by the great pageant of 1905 which was held to celebrate the 1200th anniversary of the founding of the town by St. Aldhelm, Sherborneʼs first Bishop.

(16) If you have more time, you might like to visit Sherborne Old Castle or Sherborne Castle and Gardens. To reach the Old Castle, leave the gardens on the far side, turn to the right and walk along Digby Road. Turn right into Half Moon Street, turn left and then right into Long Street. Cross the road onto Castleton Road and follow the road until you reach the Castle gates. This will take about 15 minutes to walk. Now managed by English Heritage, the Old Castle was built in the early 12th century by Bishop Roger of Salisbury. It was acquired by Sir Walter Raleigh in 1592, but he was unable to convert it into a comfortable home and so he built Sherborne Lodge, now the New Castle, instead. The Old Castle was twice besieged in the 17th century during the Civil War and after the second siege in 1645, when the buildings were badly damaged, Parliament ordered that it be destroyed. The remains are very impressive and a model of the castle in its original state can be seen at Sherborne Museum.

(17) It will take about 20 minutes to walk from the Old Castle to Sherborne Castle and Gardens. Walk back along Castleton Road and at the end turn left and left again onto New Road. After about 15 minutes walk you will see signs for the Castle and Gardens on your left. The Castle was built on the site of a former hunting lodge which Sir Walter Raleigh started to convert about 1594. The Digby family became owners of the castle in 1617 and it has remained with the family ever since. You can discover all its fascinating history and see its fine collection of pictures, porcelain and furniture. The castle grounds and lake were designed by the famous ʻCapabilityʼ Brown.