1 From the tourist information centre on Bell Street turn left, down the road. Walk past a row of terraced houses, built with stone below, brick above and thatch on top. Turn right, down Mustons Lane. Pass a Palladian former church on the left, now a restaurant. At the High Street turn right.
The town of Shaftesbury was founded by the Saxons. In medieval times it became an important pilgrimage site. In later centuries it was a centre for button making and served as a coaching stop on the main route to the West Country.
2 The High Street broadens into a market square by the Mitre pub, with medieval St Peter's Church and the Town Hall. Ahead is an attractively jumbled line of shops and houses. Walk up to the end, cross at the zebra crossing by King Alfred's Restaurant, and hook back down to the left. Go down the narrow lane beside the Town Hall and between the houses and you'll suddenly find yourself at the top of Gold Hill, with the line of cottages tipping down the steep, cobbled road ahead, and a perfect view of the green Dorset hills behind. At the top is the Town Museum. The view is only slightly marred by a giant fibreglass loaf, testimony to the restoration of the street in 1980.
3 The massive, buttressed grey walls of Shaftesbury Abbey stand opposite the houses on Gold Hill. Walk down the hill - it is genuinely charming, if hard on the knees - to James Street. Turn left and follow the road along the contour of the hill. After almost ½ mile (800m) pass the junction with French Mill Lane and continue ahead, up Hawkesdene Lane. At the top turn right and cross the stile to enter the quaintly named Wilderness Park. Follow the grassy path above the trees and down, with Melbury Hill dominating the view to the right. Cross the stile at the end and turn immediately right, along the edge of the field. Cross another stile then turn left down the narrow lane. Continue down the hill between steep banks, passing French Mill Cottage on the right.
4 At Three Ways Cottage turn right. Pass a turning to Gears Mill and follow the road as it climbs steadily back up to the town, the horizon punctuated by the three square church towers of St Peter's, Holy Trinity and St James's. Pass Holyrood Farm on the left, and keep straight on up the hill. Just after a post box, and before a road junction, take the steep and uneven footpath down to the left. The path rises and becomes broad Kingsman Lane, a road between houses. At the top turn left on to James Street, tightly-packed with terraced cottages. Pass Ye Olde Two Brewers Inn on the left and pause to admire the Pump Yard on the right.
5 Turn right, up Tanyard Lane. At the top turn right by some garages. Almost immediately turn left up a cobbled path by house No 3. This steep path leads up to the top of the town, and the views improve as you climb. Steps lead on to a tarmac path, with a well-placed bench. At the top turn your back on the view and go through a small gate in the wall. Turn left along Love Lane and take the first path up to the right between houses, called Langford Lane. At the end turn right. Cross the road then, just beyond the ambulance station, turn left down a path, signposted 'Castle Views'. This leads to a vantage point with superb views out to the north. You will see as far as Glastonbury Tor on a good day. Return to the main road and turn left, passing Ox House. Cross back then turn right, down Abbey Walk, passing an old pump on the corner. Pass the curious Old School House on the left and turn left at the war memorial. Pass the entrance to the abbey ruins.
6 At the end of the walkway keep left, to emerge by a wonderful, old-fashioned confectioner's shop and the King Alfred Restaurant. Bear left, cross at the zebra crossing and keep left, passing the Georgian Grosvenor Hotel. Keep right, into Bell Street to return to the tourist information centre.