A guide to walking in Winchester

Whether you’re a seasoned rambler looking for your next big hike or a city stroller wanting to take in the sights more sustainably, the Winchester district has something for every type of walker.

Winchester District Gilbert Yates Photography 27 of 94
There are so many reasons to put on your walking boots and explore the great outdoors this year. Not only does walking improve your physical health, it can also improve your mood, reduce stress, and help you sleep better. And where better to dust off the cobwebs than historic Winchester?

For the pub walkers

Itchen Navigation Heritage Trail (1 hour)

The Itchen Navigation Heritage Trail stretches from Winchester in the north, to Woodmill in the south. For a more manageable walk (and the best pub stops) we recommend doing just a section of the trail, such as Winchester to Shawford (around 1 hour). The trail begins at The Black Boy pub in Winchester, named after the small boys who got dirty unloading cargoes of coal from the barges at the nearby wharf on the Navigation. It is full of old curios and antiques so definitely worth a visit either at the start or end of your walk.

Once on the trail, you’ll pass various Winchester landmarks such as St Catherine’s Hill, an Iron Age hill fort, Hockley Viaduct, a restored Victorian railway viaduct, and Compton Lock, a popular spot for wild swimming! If you choose to finish the trail in Shawford, stop at The Bridge Inn, an idyllic riverside pub offering delicious food, a stunning terrace and well-earned draught beers.

If you don’t fancy the walk back to the city, catch the Number 1 bus from Compton Street to Winchester Bus Station. Or, if you came to Winchester using the Park & Ride service, hop on the P&R bus from South Car Park (a 20-minute walk from The Bridge Inn) to your car.

Image: Itchen River

Itchen River 13 copyright WCC
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For the dog walkers

St Catherine's Hill (1 hour)

Dog walkers can experience panoramic views of Winchester from St Catherine’s Hill, an iron age hill fort on the edge of the South Downs. From the city centre, take the 30-minute walk along The Itchen Navigation Trail (see above), past The Handlebar Café, until you see the gate on the left to St Catherine’s Hill.

Head up the steps to the summit of the hill where you’ll be greeted by stunning views of the city, a copse of beech trees (the former site of a Norman chapel), and the 17th century turf ‘mizmaze’. There is plenty of wildlife to look out for as well including green woodpeckers, 25 species of butterfly and rare orchids dotted through the grasslands. You might even bump into some grazing livestock, so be sure to always keep your dog under control.

Back down the hill, the opposite way you climbed up, you can enjoy some locally sourced food and a delicious house blend coffee from the Handlebar Café. It is open 9am to 4pm every day and is very dog friendly!

Dog carrying a ball
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For the history walkers

Cheriton Battlefield Walk (3 hours)

Winchester has a rich and varied military history, most famous for King Alfred the Great, who fortified Winchester against the Danes and established it as the royal centre of Wessex. However, a slightly lesser-known aspect of Winchester’s military history can be found just 8 miles outside of the city.

The Battle of Cheriton was a major turning point in the English Civil War and resulted in an important Parliamentarian victory that helped shape the future of England. Follow a trail setting out from the Parliamentarian camp at Hinton Ampner and embark on the walk taken by the troops on 29 March 1644 to the Cheriton Battlefield.

The full walk is just under 9km long and will take you around 3 hours. You can finish your walk with food and drink at The Hinton Arms or a stroll around the stunning Hinton Ampner house and gardens.

Image: Battle of Cheriton re-enactment

Cheriton
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For the city walkers

City Walk (1 hour)

If you are only in the city for the day and don’t want to miss a thing, the City Walk is the perfect place to start. The walk begins at the Winchester Visitor Information Centre, in the Victorian Guildhall, where you can purchase a copy of the trail.

You will meander along the bank of River Itchen towards Kingsgate Village. Stop here for some lunch at the award-winning Wykeham Arms, shop for books in the wonderfully quaint P&G Wells, and perhaps go for a tour of the medieval Winchester College. If you plan to visit in the summer of 2025, you must book tickets to No. 8 College Street, the house Jane Austen spent the final weeks of her life.

The trail will then lead you to Winchester Cathedral, where you can step inside to see the early Norman crypt, the ornate Renaissance chantry chapels, Jane Austen's grave and the Great West Window.

Exploring the Upper City, you will be led past the City Museum, The Great Hall of Winchester Castle and The Westgate Museum, all of which you can access for 12 months with the Historic Winchester Explorer ticket!

Past the Great Hall, you will enter Peninsula Barracks, once the site of Charles II unfinished King’s House and now home to Winchester’s Military Museums. Each museum offers a unique experience and has its own story to tell; many are also free to enter.

Once you’ve made your way back to the city centre, be sure to stop by the Winchester Visitor Information Centre, where you can browse a selection of local makers’ wares and gorgeous souvenirs.

Image: Winchester Cathedral

Winchester Cathedral
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For the countryside walkers

The Millennium Trail & The Alre Valley Trail (1 hour)

Alresford is a Georgian town famous for its watercress, specialist shops, old-fashioned inns, and the Watercress Line steam railway. Explore this beautiful corner of Hampshire’s countryside with The Millennium Trail & The Alre Valley.

The Millennium Trail begins at The Station Yard, where you can park your car (or walk to from the platform if travelling by train). It will lead you through the main streets of the town, exploring its rich history and notable landmarks. At Arlebury Park, you will be able to divert onto The Alre Valley Trail.

Walk along the river Alre to discover Old Alresford, including Eel House, Alrebury Park House and panoramic views of the Alre Valley. Be sure to keep an eye out for waterbirds, especially during migration periods in Spring and Autumn, or the birds of prey that hunt here all year round.

After rejoining the Millennium Trail, you will be brought back to the town proper. Enjoy a bite to eat at one of Alresford’s cafes and pubs or explore the delightful selection of independent shops. If you have the time, The Watercress Line is certainly worth a visit – hop on at Alresford and enjoy unlimited travel to Ropley, Medstead and Alton on the heritage steam railway.

Image: Alresford Mill

Alresford mill
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For the experienced walkers

South Downs Way: Winchester to Exton (4 hours)

For experienced walkers, the South Downs Way is the perfect route to explore some of the country’s most breath-taking scenery. The first stretch of the Way is from Winchester to Exton, a quaint village nestled in the South Downs National Park.

We recommend fuelling your journey in Winchester by stopping at one of the city’s breakfast and lunch spots: The Refectory at Winchester Cathedral is an ideal meeting place for fellow hikers, while the bike-themed South Downs Social provides the perfect backdrop for a pre-trail coffee.

Along the route, you will pass the small village of Chilcomb and climb to Cheesefoot Head, taking in the spectacular views of the South Downs. The route then descends into Exton where this first stretch of the Way ends.

In Exton, you can enjoy a well-earned meal at The Shoe Inn and stay overnight at Corhampton Lane Farm. They are well-equipped for walkers, offering collection from Exton at the end of your days walk, packed lunches and laundry facilities.

Image: South Downs National Park

Cheesefoot head sdnp
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