Head off on a walking trail with a perfectly-planned pub stop on route
Does anything go together more perfectly than a wholesome walk and a trip to the pub? If you don't fancy putting on your walking boots without knowing where you'll be drinking your post-hike pint, read on.
There are so many amazing walking routes in and around Winchester. Here are five that take you past or conclude at characterful pubs, where you can order a refreshing pint of something local, eat a well-deserved Sunday roast or take a rest in a sunny pub garden.
Some of these walks start in Winchester city centre, while others begin in lush South Downs countryside. They range from short city circulars to longer walks with multiple stops that could fill a whole day. For more routes and trails, read our full guide to Walks in Winchester
Curated by the Visit Winchester team.
Created: 5 May 2026
Easy Winnall Moors Loop
Spot local wildlife and explore a peaceful nature reserve right in Winchester city centre on this simple circular.
Distance: Approximately 1.7 miles
Start: King Alfred Statue
📍Winchester city centre
From Winchester's iconic King Alfred Statue, head onto Bridge Street, crossing City Bridge and admiring Winchester City Mill (it's free to enter if you have time). Turn left between Pizza Tavern and Kyoto Kitchen (two very good options for food once you've finished your stroll) onto Water Lane and follow the River Itchen towards Winnall Moors.
Cross over Easton Lane and find the entrance to the nature reserve, which is marked by a large wooden arch. Follow the trail around Winnall Moors Nature Reserve, a nature-rich wetland where the River Itchen flows. There is a loop, made up of footpaths and boardwalks, which will bring you back to where you entered the nature reserve.
🍺Pub pitstop: The Willow Tree, Winchester city centre. Head out of Winnall Moors the way you came and turn right before crossing over Easton Lane. The Willow Tree pub will be right in front of you. The dog-friendly pub has a riverside garden.
🍺Pub pitstop: The Bishop on the Bridge, Winchester city centre. Head back the way you came along Water Lane and you'll find The Bishop on the Bridge opposite Winchester City Mill. The pub has a great beer garden overlooking the river.
End: King Alfred Statue
📍Winchester city centre
Make it longer? Take the path to the side of The Bishop on the Bridge to follow the River Itchen along The Weirs. The path will take you to College Street, where you pass Wolvesey Castle, Winchester College, P&G Wells bookshop and the building where author Jane Austen died. The Wykeham Arms is well located here for another pub stop too. From here you can pass through Priors Gate into Winchester Cathedral's Inner Close towards the cathedral itself and Winchester High Street.
Alresford's Millennium & Alre Valley Trail
Follow a trail through the pretty market town of Alresford, which is known for growing watercress, and its surrounding countryside.
Distance: Approximately 2.7 miles.
Start: Alresford Train Station
📍Alresford
This route starts and finishes in Alresford. Coming from Winchester? You can catch the 67 or 64 bus to Alresford. Set off from Alresford Train Station - it's the start of The Watercress Line, a heritage railway which runs between Alresford and Alton and is populated by vintage steam trains. You'll be following The Millennium and Arle Valley Trail, but in reverse. Pick up The Millennium Trail, passing through the churchyard of St John the Baptist. When you step out onto West Street, turn left, cross the road and head down the hill. Follow Pound Hill and walk along The Avenue until you come to Drove Lane. The route takes you out of the centre of Alresford to find the River Arle, where you'll see historic Eel House, before heading back towards the town.
You'll pass an honesty table selling duck food, the beautiful timber framed Fulling Mill and wild watercress growing in the river. The path takes you past historic houses on Mill Hill to the bottom of Broad Street. Here you will briefly detour from the route to find your pub stop.
🍺Pub pitstop: The Globe, Alresford. A charming 15th-century pub, The Globe has roaring fires in winter and a large sunny beer garden to enjoy in the summer months, with dreamy views over Old Alresford Pond.
Afterwards, head back to Broad Street and walk up the wide, tree-lined street where you'll find indie shops and cafés to explore. At the top, cross over and find the passageway into the churchyard and the station beyond, where you started your walk.
End: Alresford Train Station
📍Alresford
The Itchen Navigation Heritage Way: Winchester to Shawford
Follow the River Itchen south out of Winchester city centre, passing through South Downs countryside before catching the train back to the city.
Distance: Approximately 3 miles
Start: King Alfred Statue
📍Winchester city centre
Start your walk in central Winchester, at the bottom of the High Street by the King Alfred Statue. From here head to Winchester City Mill and the River Itchen. Follow the river along by The Weirs, crossing the water at Wharf Mill.
🍺Pub pitstop: The Black Boy, Winchester. Your first pub is The Black Boy, a characterful watering hole near the River Itchen full of curious knick knacks. It's on Wharf Hill. Too early for a pitstop? Keep going and reward yourself with a pint at the end of your walk instead.
From here head onto Domum Road where you'll find your first waymarker for The Itchen Navigation Heritage Trail. They are dark blue with a green dragonfly.
Follow the waymarkers and they'll lead you out of Winchester city, past ancient hill fort St Catherine's Hill on your left. (Take a detour to climb the 300+ steps to the top for views back over Winchester if you have time.) Tracing the route of the waterway, the walk leaves Winchester running through Hockley Meadows, past Compton Lock and Twyford Meads before bringing you to the village of Shawford and your well-deserved pub stop.
🍺Pub pitstop: The Bridge Inn, Shawford. A riverside pub with a pretty beer garden, The Bridge Inn also serves food, from burgers and salads to Sunday roasts.
Finish up at the pub and head over the road to Shawford train station to catch a 5-minute train back into Winchester city centre.
End: Shawford Train Station
📍Shawford
Make it longer? Walk back to Winchester instead! Then you'll definitely have earned a stop at The Black Boy on your return.
Alternatively keep following The Itchen Navigation Heritage Trail. The full 10-mile route takes you past Eastleigh, where you could get on a train back to Winchester, to Woodmill near Swaythling, where there is also a train station.
Classic St Catherine's Hill circular
Walk out of Winchester's historic city centre into South Downs National Park countryside and back, climbing an Iron Age hill fort and passing the ancient Hospital of St Cross.
Distance: 4-5 miles
Start: Winchester Cathedral
📍Winchester city centre
Admire Winchester Cathedral before heading into the Inner Close. Walk through ancient Priors Gate, pass under St Swithun-upon-Kingsgate church and you'll find yourself in pretty Kingsgate Village. From here you will walk along College Street, past No 8, the building where author Jane Austen died, historic bookshop P&G Wells, Winchester College and the ruins of Wolvesey Castle (it's free to enter if you have time). Take College Walk and then Domum Road, following Itchen Navigation Heritage Trail waymarkers towards St Catherine's Hill.
You'll follow chalk stream the River Itchen out of central Winchester, crossing over Garnier Road and passing a small car park and the Cadence Clubhouse café.
Keep following the river until you see a wooden gate on your left. Pass through it and climb the more than 300 wooden steps up to the top of St Catherine's Hill, an ancient Iron Age hill fort topped by a copse of trees which offers amazing views back over Winchester city. Look out for the mizmaze!
Return down the steps, go back through the wooden gate and turn left. From here, follow the Itchen Navigation Heritage Trail again until you come to Five Bridges Road on your right. Follow signs towards The Hospital of St Cross and then follow Keats Trail back into Kingsgate Village for a well-deserved drink. If you have time, stop off at The Hospital of St Cross to explore the ancient chapel and almshouse.
🍺Pub pitstop: The Wykeham Arms, Winchester city centre. Start or end your walk at The Wykeham Arms, a characterful pub which serves great food.
🍺Alternative pub pitstop: The Queen Inn, Winchester city centre. If a spacious sunny pub garden is what you're after, head to The Queen Inn instead. It's near the end of your walk on Kingsgate Road.
End: Kingsgate Village.
📍Winchester city centre
Make it longer? Instead of turning right into Five Bridges Road, keep walking to explore the Hockley Viaduct as part of the Viaduct Way walk.
Make it shorter? Once you've descended St Catherine's Hill, head back the way you came to Garnier Road. Rather than crossing back over, turn left and follow the road until you come to Kingsgate Road. Here, turn right and you'll find yourself passing The Queen Inn and The Wykeham Arms before arriving back in Kingsgate Village.
The Itchen Way: Hinton Ampner to Itchen Stoke
Walk a section of the full 30 mile route which runs from the source of precious chalk stream the River Itchen in pretty Hampshire countryside to where the river meets the sea at Southampton.
Distance: Approximately 7 miles
Start: Kilmeston Road (///unlisted.olive.prefer)
📍near New Cheriton
This walk starts at the source of the chalk stream, which which is by Kilmeston Road, near National Trust property Hinton Ampner. If you're beginning in Winchester city, catch the 67 bus to the start of The Itchen Way route (Bus stop: New Cheriton, Petersfield Road). From here pick up The Itchen Way, which is clearly waymarked with yellow arrows on a green background.
🍺Pub pitstop: The Flower Pots Inn, Cheriton. You won't have been walking long when you hit your first pub. A short detour from the route in the pretty village of Cheriton will take you to The Flower Pots Inn. It's a charming pub with a huge beer garden, where their beer is brewed on site. Get back on The Itchen Way and keep following the waymarkers.
🍺Pub pitstop: The Tichborne Arms, Tichborne. Your next stop is a mini detour to The Tichborne Arms, a popular foodie destination with a pretty garden and outdoor pizza oven. It's a few minutes walk off The Itchen Way. Pause for something to eat here, or hold on until your next stop. From here, get back on The Itchen Way until you reach Ovington.
🍺Pub pitstop: The Bush Inn, Ovington. Enjoy a rest or a meal at this characterful pub, which has a beer garden beside the river, before crossing the river and walking up to Itchen Stoke, where you can catch the number 67 bus back to Winchester.
End: Itchen Stoke.
📍Itchen Stoke village
Make it longer? Keep following The Itchen Way after The Bush Inn, rather than catching the bus. The walk from Hinton Ampner to Winchester is approximately 14 miles. If you want to keep up the pub crawl, look out for The Plough Pub in Itchen Abbas and The Chestnut Horse in Easton. You could also end your day at The Bishop on the Bridge pub in Winchester city centre.
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