When the New York Post calls Winchester the best city to visit at Christmas, you know you’re in for something special. This Winchester Winter Market walk guides you through the city’s key landmarks, from its historic streets to its famous cathedral, before finishing at the Christmas Market for some well-earned browsing. To avoid wasting time figuring out where to go, download the GPS map at the end of this post and enjoy a seamless festive stroll.
Last Updated: 6/12/2025
As the year draws to a close, the Christmas spirit begins to take over towns and cities across the UK. From Canterbury and Oxford to Kingston upon Thames, festive markets pop up everywhere. In this guide, I take you on a Christmas Market walk through Winchester, exploring the city’s highlights before arriving at its renowned Winter Market.
Logistics of the Winchester Winter Market Walk
- Distance:4 miles (6.4 km)
- Total Ascent: 161 ft (49 m)
- Highest Point: 322 ft (101 m)
- Walking Estimate: 1 hour and 40 minutes
- Difficulty: Easy
How to get there:
- Direct trains from LondonWaterloo Station to Winchester.
- The journey takes 1 hour and 15 minutes.
For the return
- Direct trains from Winchester to London Waterloo
- It is a circular walk so you can buy a day return ticket.
What to pack:
- Comfortable clothing and footwear – Dress for the weather and choose shoes suitable for walking
- A backpack – Handy for carrying layers, water, and any small purchases from the market.
- Snacks – Ideal for a quick boost along the way.
- Packed lunch – Bring one if you don’t plan to eat at the Winter Market.
- Rain gear – Essential if rain is in the forecast.
Additional Information
- There are toilets available at Winchester Station
- There are public toilets at the Winchester Winter Market
- This is a stile-free walk
- Dog-friendly walk
Where to eat and drink:
- Winchester Winter food stalls (I highly recommend the tartiflette)
Winchester Winter Market Walk Map
Do you want to do this walk? Simply download the GPS map by clicking on the link below. If you require a little extra help to learn how to upload the map onto your navigation app, follow my step-by-step guide here.
Highlights of the Winchester Winter Market Walk
- Winchester Cathedral
- Buttercross
- Town Clock
- Guildhall
- River Itchen
- St Catherine’s Hill
- Winchester College
- Winchester Winter Market
- Carol Service at the Cathedral
The Winchester Winter Market Walk
So now we covered the basics, let’s get to the walk!
Winchester
Welcome to the Medieval City of Winchester. The city has a long and fascinating history, with evidence of prehistoric settlements including three Iron Age hillforts surrounding the area—one of which, St Catherine’s Hill, you’ll visit on this walk.
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A little bit of history
The town flourished under Roman occupation and became one of the largest Roman settlements in Britain. After the Romans withdrew, Winchester shrank in size and evolved into an important religious centre.
Winchester later became the heart of royal administration under King Alfred the Great. Today, a statue of the king—sword raised in triumph—stands prominently on Broadway to commemorate his legacy.
The city’s most iconic landmark is Winchester Cathedral, which you’ll also visit on this walk. Built in 1079, it remains the longest Gothic cathedral in Europe and marks the starting point of the Pilgrims’ Way, a 119-mile (192 km) route that medieval pilgrims followed to reach St Thomas Becket’s shrine in Canterbury.
Town Center
Your walk begins at Winchester Train Station. From the station, head up Station Hill and continue onto City Road. At the crossroads, turn right onto Jewry Street, passing St Peter’s Church, a Roman Catholic church built in 1924. At the end of the street, turn right onto the High Street.
As you wander down the High Street, you’ll pass several key Winchester landmarks:
- The Buttercross – A fifteenth-century monument decorated with twelve statues representing the Virgin Mary and various saints. It marks the site of the medieval market.
- The Town Clock – Hard to miss, this projecting clock was erected in 1713.
- The Guildhall – Built in 1875 on the former site of an abbey dissolved in the 1530s by order of Henry VIII.
After passing the Guildhall, you’ll reach the Offices of the Mayor of Winchester, followed by the entrance to Abbey Gardens.
River Itchen
Behind Abbey Gardens, turn right just before the bridge. Follow the footpath that brings you onto the banks of the River Itchen. This 26-mile (42 km) chalk stream begins near New Alresford in Hampshire and flows south to Southampton, where it joins Southampton Water.
Continue along the towpath beside the river. As you walk, you’ll spot the rear of St Peter Chesil Church, a twelfth-century building now transformed into a 75-seat intimate theatre. Since 1966, it has been home to the Winchester Dramatic Society.
Continue along the path until you reach a wooden bridge. Do not cross this one—instead, keep following the footpath to its end, where you’ll come to a second bridge. Cross over this bridge to continue the walk.
Turn right onto College Walk and, when the road bends, continue straight ahead onto Domum Road. A little further along, you’ll see a footpath on your right. Follow it and cross the bridge to rejoin the towpath along the Itchen Navigation.
Continue your stroll beside the river. This section of the walk is flat and very gentle, making it a pleasant stretch to enjoy the scenery. Along the opposite bank, you’ll pass a row of riverside houses, followed by the Kingsgate Lawn Tennis Club and Palmer Field.
At the end of the towpath, turn left onto Garnier Road, then take the next right into a small alley that leads to a car park. Walk straight across the car park and you’ll find the footpath on your right. This is where the climb up St Catherine’s Hill begins.
St Catherine’s Hill
Here are some facts about St Catherine’s Hill.
How high is St Catherine’s Hill?
324 ft or 99 m.
Why is it called St Catherine’s Hill?
St Catherine’s Hill takes its name from St Catherine’s Chapel, which once stood at its summit over 900 years ago.The chapel was destroyed in 1537, but its remains are still buried beneath the beech trees you see at the top of the hill today.
How many steps does St Catherine’s Hill have?
333 steps (minus a broken one)
Long before the Romans arrived in Winchester, St Catherine’s Hill was already inhabited. Around 2,500 years ago, Iron Age tribes built a hillfort at the summit. They lived on and around the hill, keeping livestock and growing crops on the lower slopes, while the fort served as a protected refuge whenever the settlement came under threat.
Ancient Mystery
Behind the cluster of beech trees, you’ll find a maze carved into the ground. Its exact origins are uncertain, but local legend offers a memorable explanation. According to the story, during the seventeenth century, a mischievous schoolboy was sent to St Catherine’s Hill as punishment. To pass the long summer days, he is said to have designed and cut the maze himself. Tragically, he died on the final day of his holiday—but the maze survived and remains visible to this day.
Do you know another explanation for the maze’s origin? Share it in the comments below.
After taking in the views from the top of the hill, begin your descent using the staircase on the opposite side. Follow the steps down until you reach the path below.
Winchester College
Once you complete the descent, turn right and follow the path at the bottom of the hill, which curves gently back toward your starting point. From here, you get a wonderful view of St Catherine’s Hill, allowing you to fully appreciate the landscape you’ve just walked across.
When you return to the car park, turn left onto Garnier Road. This route leads you back toward Winchester town centre via Winchester College.
Founded in 1382 by William of Wykeham, Bishop of Winchester, the College still stands on its original grounds. It is a boarding public school which, in England and Wales, means a fee-charging school open to pupils from any background or location. When it first opened, the College educated around 70 boys—a number that has increased tenfold today.
As you follow the towpath beside the River Itchen, you’ll spot the College’s red-brick Science building on the opposite bank. Continue along the river, where swans glide across the water and sheep graze in the meadows. When you reach College Walk, follow the path around the Warden’s Garden, then turn left onto College Street.
Winchester Winter Market – What to Do and See?
At the end of the street, you’ll come face to face with an old grey-brick building supported by a series of arches. Walk underneath the arches, where the wooden beams are exposed overhead. On the other side, you’ll emerge in front of a brick gateway decorated with an ornate coat of arms.
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Follow the road as it passes beneath the gate and continues through a small cluster of medieval timber-framed houses. At the end of this street, you’ll arrive at the Winchester Winter Market.
First launched in 2006 with just a handful of stalls, Winchester’s German-influenced Christmas Market has grown into a magical event featuring 112 chalets and welcoming over 400,000 visitors each year. As you enter the square, you’ll be greeted by giant cauldrons bubbling with mulled wine, filling the air with festive aromas.
Take your time wandering between the stalls, where you’ll find handcrafted gifts, seasonal treats, and Christmas decorations. When you reach the Cathedral, you’ll see the food market just opposite, at the centre of the square. Here you can enjoy a range of dishes and drinks—from French tartiflette and German-style sausages to soft drinks, beers, and other festive favourites.
Bon appetit!
After your food break, enjoy the sound of the carol singers performing in the food square. When they finish, follow them into the Cathedral for a 30-minute carol service, a wonderfully atmospheric pause in the middle of your visit.
As you leave the Cathedral, head up the nearby staircase to the Dean Garnier Garden, where you’ll find the Artisans’ Market.
When you’re ready to leave, exit the Winter Market and walk around the Cathedral, then begin making your way back toward the train station.
Have a safe journey back to London!
Final Thoughts on the Winchester Winter Market Walk
If you enjoy combining Christmas shopping with a scenic winter walk, why not explore my Best Winter Walks Near London selection? It’s the perfect way to embrace the crisp winter air and the festive atmosphere all in one day.
And you—what’s your favourite Christmas walk? Let me know in the comments below.
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