Finding the South Downs Way trail from Winchester city center can be a bit confusing. The trail is not well-marked, so if you don’t know where you’re headed, it can be difficult to find.
To get to the South Downs Way trail from Winchester, find the High Street in Winchester. Facing east, walk along the Winchester High Street until it becomes Broadway and then cross the bridge over the river. Turn right on Chesil Street and walk for about 200 meters. Turn left on East Hill, then veer right on Petersfield Road. When Petersfield Road ends, follow the path of the South Downs Way trail from Winchester and turn right when it splits. You will then cross a bridge over a motorway. Take a left when you are across, then a right when you come to the fence. At this point, you will be on the South Downs Way
