Winchester, the River Itchen and Cheesefoot Head loop — South Downs National Park

Venture to the historic city of Winchester and embark on a picturesque loop around the northwestern corner of the South Downs National Park, surrounded by the serene waters of the River Itchen.

Begin your adventure by starting on the South Downs Way from its inception in Winchester. Follow the path along the tranquil banks of the River Itchen, leading you to the majestic St Catherines Hill. Ascend to Cheesefoot Head, a natural amphitheatre and beauty spot that provides sweeping vistas of the South Downs. As you make your way down, you'll navigate through a series of open gravel tracks to the charming village of Tichborne.

For the return leg to Winchester, you’ll meander along idyllic country lanes that run parallel to the River Itchen, while passing historic villages and a grand 16th-century country house.

As well as the South Downs Way, you'll trace parts of King Alfred's Way, a long-distance bikepacking circuit that links historic cities of cultural landmarks of south England.

The route is split equally between road and off-road with a mix of gravel tracks, traffic-free paths, grassy bridleways and quiet country lanes. The off-road sections are generally well-surfaced with nothing too technical to contend with. Some sections of the King Alfred's Way are a little overgrown in places, so prepare for a few close encounters with nettles. A gravel or mountain bike is best suited for this loop.

Food stops are abundant on the second half of the Tour with three country pubs en route. Your first option is the Tichborne Arms in Tichborne, a charming thatched roof pub boasting an alluring garden setting. Continuing on, you'll come across the Bush Inn in Ovington, a historic 17th-century establishment nestled alongside the picturesque River Itchen. Then, in the village of Easton, awaits The Cricketers Inn, a traditional pub with a log fire.

You begin and conclude your journey in Winchester, a vibrant city with welcoming pubs, cosy cafes and convenient supermarkets.

Winchester station is served by regular trains from London Waterloo, Clapham Junction and Southampton. It also has an hourly Cross Country service, which runs between Bournemouth and Manchester. Parking in Winchester is limited, so if you're travelling by car I'd recommend starting in the village of Easton where you'll find a number of on-street parking spaces.