Are you looking for the very best walks in Winchester? You’ve come to the right place!
From hilltop hikes to riverside strolls, Winchester has it all. Whether you’re a local looking for a new adventure or a tourist looking to explore, this article will guide you through 15 of the best walks in Winchester.
From St. Catherine’s Hill to the Grange Estate, you’ll find something to suit all tastes. So get ready to lace up your boots and get out and explore Winchester’s stunning countryside.
Let’s take a look at the best walks in Winchester!
St. Catherine’s Hill

St. Catherine’s Hill is a beautiful spot for a leisurely stroll – you won’t be disappointed! The hill is located on the outskirts of Winchester and offers stunning views of the city.
It’s a favourite spot amongst locals, renowned for its lush green grass and abundant wildflowers. The path up the hill is an easy walk and takes around an hour to reach the top.
Once you’ve reached the summit, you’ll be rewarded with sweeping views of the city and surrounding countryside. There are plenty of benches dotted around the hillside to take a break and enjoy the scenery.
The hill is also a great spot for bird watching, as you may be lucky enough to spot some rare species of birds. For a more challenging walk, there is a longer route that takes around three hours to complete.
It’s a great way to explore the area and take in some of the stunning scenery.
Itchen Navigation

Experience the best of Winchester’s outdoor scenery by taking a stroll along the Itchen Navigation.
This walk meanders along the River Itchen, and it is a beautiful and tranquil journey.
It is also a great way to explore the area and take in the sights.
The path passes through a variety of landscapes, from meadows and woodlands to parklands and riverside scenery.
Along the way, you’ll spot a variety of birds, animals, and plants.
This makes it a great place to observe nature.
You can also take a break at The Chequers Inn, a traditional pub that serves a range of refreshments and snacks.
This walk is perfect for anyone looking for a peaceful break surrounded by nature.
River Itchen

The River Itchen is a stunning natural sight, winding its way through the countryside and offering breathtaking views.
Flowing through the historic city of Winchester, the river is a great destination for a leisurely stroll or an adventurous hike.
The path follows the river for miles, taking you through a variety of landscapes, from wide open fields to shady woodlands.
As you meander along the riverbank, you’ll find plenty of wildlife to observe, including kingfishers, herons, and even an occasional otter.
If you’re lucky, you might even spot a deer or two!
The river is also a great spot for fishing, with plenty of carp, pike, and trout to catch.
Whether you’re looking for a peaceful stroll or an exciting outdoor adventure, the River Itchen is the perfect place to explore.
St. Giles’ Hill
Take in the stunning views of Winchester from atop St. Giles’ Hill, a great spot for a leisurely stroll or an exciting outdoor adventure. Set atop the hill is a castle-like building, the City Mill, an 18th-century flour mill set within a defensive wall. Take a moment to appreciate the beautiful architecture, then carry on along the path to the summit.
From here, take in the breathtaking views of Winchester and its surrounding countryside. You can even spot the South Downs and the Isle of Wight on a clear day.
St. Giles’ Hill is also the perfect spot for a picnic or a jog, with plenty of paths to explore. Make sure you keep your eyes peeled for the stunning array of flora and fauna, including wildflowers and butterflies.
Enjoy the tranquility and the fresh air as you take in all that Winchester has to offer.
St. Cross Circuit
Enjoy a peaceful, picturesque walk around St. Cross Circuit and marvel at its historic monuments, hidden gems, and beautiful views.
This 4-mile circular walk around the grounds of St. Cross Hospital is a wonderful way to explore the city of Winchester while being surrounded by its beauty. It’s easy to follow the route, as there are several signs and information boards dotted around the area.
St. Cross Circuit is a great place to take in the sights of Winchester and its surrounding areas. The route will take you past some of the city’s most iconic landmarks, including Wolvesey Castle, St. Peter’s Church, and the old Roman walls. There are also plenty of hidden gems to discover, such as the tranquil water gardens and a variety of wildlife.
At the end of the walk, don’t forget to take a moment to appreciate the incredible views of the city.
Stanmore Country Park
Delve into nature and explore Stanmore Country Park, a tranquil escape from the city of Winchester.
The park has a number of routes to explore which meander through the beautiful countryside. The views of the surrounding area are stunning, and you can spot birds of prey soaring above you in the sky.
You’ll come across a variety of wildlife during your walk, and you can even spot some of the local deer.
Whether you’re looking for a peaceful stroll or a challenging hike, Stanmore Country Park has something to offer for everyone.
The routes are well-marked and easy to follow. There are also plenty of benches and picnic areas to relax and take in the scenery.
Stanmore Country Park is a great way to get away from it all and enjoy some time in the great outdoors.
River Alre
Exploring the River Alre is a great way to connect with nature and experience the beauty of Winchester’s countryside. With its crystal clear waters, lush green banks, and an abundance of wildlife, this river is a sight to behold.
Meandering through the countryside, the River Alre is a perfect way to spend a relaxing afternoon, with plenty of spots to enjoy a picnic or take some pictures.
The River Alre is also a great place for birdwatchers, with a wide variety of species to be found along its banks. Whether you’re looking for kingfishers, herons, or ducks, you’re sure to find something to enjoy.
There are also plenty of spots to fish along the river, so if you’re feeling adventurous, why not try your luck?
The River Alre is a great way to explore the beauty of Winchester and its surrounding countryside.
Meon Valley Way
Leaving the River Alre behind, I set out on the Meon Valley Way.
This delightful walk takes you along the River Meon, known for its meandering path through the Hampshire countryside. It offers incredible views of rolling green hills, as well as the chance to explore some of the area’s most beautiful countryside.
As I walked along, I noticed the abundance of wildlife that inhabits this area, including rabbits, badgers, deer, and even otters.
The Meon Valley Way also passes through some of the most picturesque villages in Hampshire, such as Droxford, East Meon, and Warnford. All of these quaint towns offer a variety of unique shops and eateries, as well as plenty of opportunities to relax and soak up the scenery.
Along the way, there are plenty of benches and picnic spots for a well-deserved break.
All in all, the Meon Valley Way is a great way to experience the beauty of Hampshire’s countryside and all it has to offer.
South Downs Way
From Meon Valley Way, I continued my journey along the stunning South Downs Way. It’s a 100 mile long National Trail that runs from Winchester to Eastbourne, taking walkers through some of England’s most beautiful countryside.
As I followed the trail, I couldn’t help but admire the rolling hills of the South Downs, the quaint villages and picturesque scenery. It’s a magical place with plenty of interesting wildlife, including birds of prey, butterflies, and wildflowers.
Along the way, I took advantage of the many stopping points to admire the views and take photographs. The trail is well-marked and easy to follow, with plenty of benches and stiles to rest on. There are also plenty of pubs, cafes, and shops along the route, so you can enjoy a well-deserved break.
All in all, the South Downs Way provides the perfect opportunity for a memorable day out in the countryside.
Shawford Circular Walk
After exploring the South Downs Way, I’m ready to take on a different adventure – the Shawford Circular Walk.
Located just a few miles north of Winchester, this 4-mile loop provides a perfect way to spend an afternoon.
The walk begins in the village of Shawford where you’ll find plenty of parking.
From here, you’ll meander along the banks of the River Itchen, taking in the picturesque views of the Hampshire countryside.
The route then continues up a gradual climb, with quaint villages, rolling hills, and an abundance of wildlife to observe, making for a truly enchanting experience.
Once you reach the top, you’ll be treated to some of the most breathtaking views of Winchester and the South Downs National Park.
The route then winds back down to Shawford, giving you a chance to refuel at one of the local pubs before heading home.
Farley Mount Country Park
Next up on my tour of Hampshire’s countryside is Farley Mount Country Park, a stunning area of grassland and woodland with plenty of trails to explore. This park has something for everyone, from the short, easy strolls around the perimeter to the more adventurous multi-hour hikes.
It’s a great place for a picnic, and there’s plenty of spots to take in the views and soak up the peace and quiet. There’s a mix of open grassland and woodland, as well as plenty of wildlife. The park is also home to the Iron Age Hill Fort, a fascinating historical site.
The park is well maintained and well signposted, making it easy to navigate. Farley Mount Country Park is a great place to escape the hustle and bustle of city life and get back to nature.
The Grange Estate
Following my tour of Farley Mount Country Park, I arrived at The Grange Estate, a sprawling estate of manicured lawns and gardens with a vast network of trails to explore.
Here, the air was filled with the fragrant smells of flowers and a cacophony of birdsong.
I was in awe of the beauty and grandeur of the estate, which spanned an area of over 400 acres.
The trails were well-maintained and offered a variety of routes to suit different levels of ability.
I chose to take the three-mile loop around the perimeter, taking in the breathtaking views of the river and surrounding countryside.
I was delighted to spot several wild deer grazing in the distance, and the occasional rabbit darting across my path.
At the end of my walk, I felt invigorated and inspired by the natural beauty of The Grange Estate.
Micheldever Woods
Heading to Micheldever Woods, I was excited to explore the ancient woodland and discover its hidden secrets.
This wood is the largest remaining ancient woodland in Hampshire, and it’s easy to see why it is so popular with those looking to explore the outdoors.
The wood is full of winding paths and trails that lead through the trees and alongside the river.
I could hear the birds singing and the river cascading over rocks as I walked, the smell of the foliage and the earth filling my senses.
I felt so peaceful and relaxed, surrounded by the beauty of nature.
The trails vary in length and difficulty, so there’s something for everyone – whether you’re looking for a leisurely stroll or a challenging hike.
There are also plenty of picnic spots and benches to take a break and enjoy the scenery.
Micheldever Woods is a truly magical spot, and a must-see for any nature enthusiast.
South Winchester Circular Walk
If you’re looking for a great way to take in the sights and sounds of Hampshire, then the South Winchester Circular Walk is a must-try.
This walk offers a great mix of historical sites, countryside, and even a short stretch along a canal. It covers a distance of 8.2 miles and takes around five hours to complete.
The walk starts in South Winchester and takes you through some of the most picturesque areas of Hampshire, including the villages of Chilcomb, Bramdean, and St. Cross.
Along the way, you’ll get to see breathtaking views of the South Downs, as well as explore some of the most interesting historical sites in the area.
You’ll also be able to take a break and enjoy a picnic lunch at the St. Cross Hospital before walking back to South Winchester.
This walk is perfect for anyone looking for a great way to experience the beauty and history of Hampshire.
Winchester City Millennium Greenway
Experience the beauty of Winchester and its surrounding area by taking a stroll along the Winchester City Millennium Greenway. This 3.7 mile circular route begins at the city center, winding along the banks of the River Itchen and through the countryside of St Catherine’s Hill and King’s Hill.
Along the way, you’ll be treated to stunning views of the city and the surrounding Hampshire countryside.
The walk is easy to follow and suitable for all ages, making it a great way to get out and explore the area. You can spot a variety of wildlife including waterfowl, deer, and a variety of birds.
As you walk, enjoy the tranquility of the area and take in the sights and sounds of the local flora and fauna. The walk offers a great opportunity to appreciate Winchester’s unique beauty and all it has to offer.
Conclusion
I’ve had a great time exploring some of Winchester’s best walks. From the beautiful Itchen Navigation to the historic St. Catherine’s Hill, there’s something for every walker.
Whether you’re looking for a leisurely stroll, a challenging hike, or a scenic picnic spot, Winchester has it all. No matter what your skill level, there’s a perfect walk waiting for you.
So lace up your boots and get out there, Winchester is waiting to be explored!