My favorite thing about returning to a place after a long absence is realizing how much I missed the first time. It’s been 9 years since my last day trip to Winchester, and now that I’m back I’m starting to appreciate its details a lot more. From hidden gardens to riverside walks, there’s so much to love about this city.

Day Trip to Winchester

Day Trip to Winchester

My day trip from London starts at Waterloo, where I hop on a train to southeast England’s Hampshire and alight at Winchester station an hour later. From here it’s a quick walk to the city center, where I stop for a coffee and croissant on Jewry Street to energize for my expedition.

Winchester, England

Fueled, I start to wander down the road. Historic buildings vie for attention with little lanes, and the floral border around a local pub delights.

Jewry Street, Winchester, England

When I’m finished ducking down the side streets I walk to High Street to soak up more atmosphere and history. It’s said to be the oldest street in any English city, which is fitting given Winchester is one of the oldest cities in Britain. The Romans established a town here, and after they left Winchester became an ancient English capital under the Saxons.

High Street, Winchester

Another place I particularly enjoy taking in the city’s past is the Great Hall, a 13th-century medieval aisled hall with a round table rumored to be that of the legendary King Arthur. I visited on my last day trip to Winchester, and while I loved seeing the table I completely missed the secret garden.

Great Hall, Winchester

Its pink roses and arched walkway have me reaching for my camera as soon as I discover it. The garden feels like such a fairytale that I half expect Lancelot and Guinevere to stroll through.

Great Hall Garden, Winchester

Back outside, I make my way to Winchester’s most famous landmark: the cathedral. The building itself is impressive, but what’s inside is equally so. The cathedral is one of the world’s longest medieval churches, and Jane Austen and other important figures are buried here.

Winchester Cathedral

The only downside is that the queue to pay the entry fee moves so slowly that I have to give up before I’m able to get in. It’s a shame, as visiting the cathedral was one of the highlights of my last day trip to Winchester.

Winchester Cathedral

My disappointment quickly fades when I stumble upon the Dean Garnier Garden, another hidden green space. Its vines and grasses embody tranquility, and I’m tempted to sit all day soaking up the silence.

Winchester Cathedral Garden

But around the cathedral I go, heading down pretty back lanes and scenic Colebrook Street to get to the River Itchen.

River in Winchester

I make a quick stop at the 18th-century Winchester City Mill, believed to be the oldest working watermill in the United Kingdom. Afterwards I head downstream past some of the most beautiful doors I’ve seen on my travels.

Door on the River in Winchester

From there sections of ancient Roman wall and the scent of summer roses lead me to Wolvesey Castle. Ruins are all that’s left of this 12th-century bishops’ palace, but I close my eyes and imagine how it would have been in Anglo-Saxon times.

Wolvesey Castle, Winchester

Then it’s back to the river, where I can’t get enough of the bucolic atmosphere. I walk beside fields and along wooden fences as the path leads me farther from the city with every step.

Winchester River Walk

Soon I arrive at the Hospital of St Cross, which houses one of England’s oldest continuing almshouses. The quadrangle and its adjacent gardens were used for the filming of Wolf Hall, and as I duck into the Norman church and explore the green spaces I’m transported back in time.

Hospital of St Cross, Winchester

But not for long. My day trip to Winchester can’t last forever, and I have to return to the present to get home. It’s been such an amazing visit, and I’ve discovered so many new details that I almost feel like I was blind last time. As I travel back to London, I already hope to return and find more on my next trip. I just hope it doesn’t take 9 years.

House in Winchester

Have you been here? What are your favorite places in Winchester?

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Day Trip to Winchester

24 Comments on Lady’s Guide to a Day Trip to Winchester

  1. Winchester looks so beautiful! I’ve wanted to go there for ages now, hopefully I’ll manage to make that visit sooner rather than later – I really love the look of all those old, historic buildings and the peaceful nature.


  2. that looks so pretty! I do love a secret garden. I haven’t been to winchester for years – I must head back after reading this

  3. Winchester has been on my bucket list for soo long, I have to visit soon as your post made me realise its beauty again. Thanks for being an inspiration 😀

  4. It’s been 14 years since I’ve been to Winchester so I definitely need to get back as well. I loved the cathedral but didn’t really see anything else. Your post has made me curious about the rest of the town, it looks beautiful.

    When I was there 14 years ago, my father very nearly lost his life. We had just arrived in England and we went to cross a street and he was looking the wrong way. My mother screamed at him when he was just a few feet from walking right into a car going fairly fast. We learned pretty quickly that you have to look right as you venture out instead of left like many of us are programmed to do. It’s a good thing to think about for all who come from countries that drive on the opposite side of the road.

  5. Hello,

    Love you’re blog. My husband and I are walking The South downs Way and this LDW ends in Winchester . I googled “day trip in Winchester and. Stumbled on you’re blog.

    So we are planning a extra day to visit Winchester.

    Greetings Sandra and Tony.

  6. We’re heading down to Winchester this weekend and reading your blog post has me very excited. I’m adding Dean Garnier Garden to the itinerary!

  7. Travelling from Canada to London in February, primarily to go to the theatre. But your blog has inspired us to take a day trip to Winchester. I had already googled “guided walking tours of Winchester”, but I have a feeling that February is not prime tourist season. Oh, well, it’s bound to be warmer than Canada!

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