Best trails in Winchester, Hampshire

264 Reviews
Looking for a great trail near Winchester, Hampshire? AllTrails has 16 great hiking trails, trail running trails, mountain biking trails and more, with hand-curated trail maps and driving directions as well as detailed reviews and photos from hikers, campers, and nature lovers like you. If you're looking for the best trails in New Forest National Park, we've got you covered. You'll also find some great local park options, like Bambridge Park Garden Centre or Thursley Common National Nature Reserve. Just looking to take a quick stroll? We've got 11 easy trails in Winchester ranging from 1.2 to 26.1 miles and from 134 to 561 feet above sea level. Start checking them out and you'll be out on the trail in no time!
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Map of trails in Winchester, Hampshire
Top trails (16)
#1 - Farley Mount and Parnholt Circular
Winchester, Hampshire, England
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Length: 6.0 mi • Est. 2 h 56 m
This is a beautiful walk around the Farley Mount area. It starts at the Farley Mount car park and you will pass the mount (the pyramid shaped folly that gives the park its name) on the way to waypoint 1. Keep an eye on the views also as this is one of the most beautiful walks. There are also Geocaches along this route if you are that way inclined. The track is a solid well trodden track for the majority of the route, the first half is pretty flat, the second half has a few very slight inclines but nothing too bad. The track and footpath is obvious and is easy to navigate. There are no kissing gates or stiles on route. Show more
#2 - South Downs Way (Complete)
South Downs National Park
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Length: 94.8 mi • Est. Multi-day
#3 - Winchester and Saint Catherine's Hill
South Downs National Park
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Length: 4.6 mi • Est. 2 h 14 m
A circular walk from Winchester railway station in Hampshire. The walk gives a lovely mix to suit all tastes. You will have chance to explore Winchester itself, a historic bustling cathedral city, before the walk passes through the tranquil water meadows and along the River Itchen. The route then climbs Saint Catherine's Hill, the site of an ancient hill fort which provides stunning views across the city, before descending and continuing along another stretch of the river and back to the city. The walk follows a mixture of pavements, river banks, towpaths and grass paths. There are a few steady ascents/descents plus one fairly steep climb up the wooden steps to the top of Saint Catherine's Hill and a fairly steep descent down the grass/gravel paths on the other side of the hill which are uneven and can be a bit slippy (if you prefer you can adjust the walk and use the steps for the descent as well). There are no stiles, just a few gates and dogs are welcome on Saint Catherine's Hill. Approximate time 2 to 2.5 hours. Show more
#4 - South Downs Way: Winchester to Exton
South Downs National Park
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Length: 12.6 mi • Est. 5 h 59 m
This is the first leg of the South Downs Way. Starting from Winchester Cathedral, begin hiking with an optional detour to St. Cross to claim the Wayfarer's Dole, a small amount of ale and bread traditionally given to travelers. If you are not doing the entire trail as a through hike, you can take a bus home from Exton. Show more
#5 - Old Winchester Hill and Halnaker Lane Circular Walk
South Downs National Park
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Length: 4.5 mi • Est. 1 h 48 m
A circular walk in Hampshire which follows part of the South Downs Way and is almost completely in the open with stunning countryside views. This walk starts pretty much at the top of a hill, so there is inevitably going to be some periods of walking up and down hill. That said, the stiff uphill walking is limited to one short and sharp section of 150 metres or so. You will need to negotiate some stiles and gates. At the end of the day, this is a breathtaking walk. Allow 2.5 hours.Show more
#6 - Hampshire Millenium Pilgrim's Trail
South Downs National Park
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Length: 29.9 mi • Est. Multi-day
With good weather and dry ground, this stretch can be done in a single, long day. However, it is better enjoyed by tackling over two days, which allows you to stop along the way. It's a beautiful route, taking in some of Hampshire's best countryside with very few sections along roadways, however this is unavoidable as you head in to Portsmouth, where it becomes far more urbanised. Starting at the entrance to Winchester cathedral, there is little to indicate the route of the Pilgrim's Trail, use the map and follow the Itchen Navigation to St Catherine's Hill. The River Itchen here is crystal clear, with Salmon, Trout and Otters to spot along the way. The view from the top of St Catherine's Hill is well worth the diversion and the climb. The route is not particularly well signposted anymore. Follow the map and you will also find yourself following along other LDPs, such as the Monarch's Way and Allan King's Way. A stop in Upham is recommended, the Brushmaker's Arms is a good spot along the trail to replenish water, use the facilities etc and isn't far off the trail. The church in Upham is rather beautiful. Continue along the trail, including using the old Roman Road that once connected Winchester with the town and port that was once at Portchester Castle. Follow the old Railway line in to Bishop's Waltham, where you will find public toilets and various shops for drinks/food etc. Continue through the old palace at Bishop's Waltham, which is well worth looking around. Due to it's proximity to the trail, Bishop's Waltham may be worth stopping at over night if you are planning on tackling this route over two days. Otherwise, the historic and beautiful Wickham is only a short diversion off the route and is well worth a visit. It can be easily reached by joining the Meon Valley Trail near the Forest of Bere. The Meon Valley Trail is a very flat and solid path that affords very easy walking that runs along the old route of the railway. When you reach the Forest of Bere, it is very difficult to stay on route and it is very easy to get the wrong trail and head very off course. Try and follow the map, use of GPS may make this easier as the trails on the maps do not really represent the trails on the ground. Continue through to Southwick, which is where the D-Day landings were planned and Allied Command were based during WWII. If you get a chance, stopping in this village is well worth it and the landlord at the Golden Lion is incredibly knowledgeable and interesting. The trail takes you from Southwick and up and over Portsdown Hill, the scenery is spectacular and afford the best views of the UK's only 'island city' (Portsmouth). On a good day the Isle of Wight is very clearly visible and the panarama stretches from Chichester to the New Forest. From Portsdown Hill, the route gets much more urban but also a lot easier. Once you are down the hill, Portsmouth is incredibly flat and easily navigated. As you head over the bridge at Hilsea and on to Portsea Island, do not follow the route along the road, as shown on the map. The correct route is to be taken along the harbour's edge, to the West of Hilsea Lagoon and rejoining the route on the map just NW of Spinnaker Drive and NE of the Lower Wade Way (Tidal). Unfotunately the map did not recognise this route as a connected walkway. The trail finishes at the International Ferry Port Terminal, which can be reached on foot. The Pilgrim's Trail continues in France to Mont St Michel. Show more
#7 - Cheesefoot Head from Winchester
South Downs National Park
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Length: 5.8 mi • Est. 2 h 48 m
#8 - Pilgrim's Trail
South Downs National Park
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Length: 1.5 mi • Est. 40 m
#9 - Avington and Ovington
South Downs National Park
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Length: 6.0 mi • Est. 2 h 25 m
Very pleasant walk with some great views over fields and beautiful rivers. There’s a lovely pub at the end, called The Bush Inn, as indicated on the trail. Enjoy!Show more
#10 - Micheldever Woods
Winchester, Hampshire, England
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Length: 2.0 mi • Est. 47 m
Micheldever Woods is especially beautiful in the Spring when there is a carpet of bluebells. This trail is great for kids and dogs. It's a good trail for a short mountain-bike ride.Show more
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