Hiking The Cotswold Way Part II: Stanton, Winchcombe and Cheltenham

Hiking The Cotswold Way Part II: Stanton, Winchcombe and Cheltenham

For our final hiking training trip before our big Swiss hike, we spent a lovely weekend in the Cotswolds hiking the Cotswold Way. We started in Moreton-in-Marsh, eventually catching the Costwold Way in Broadway and then onto Stanton from there, where we spent the night in a gorgeous B&B, the Old Post House (read all about it here). Our second day of hiking was spent entirely on the Cotswold Way, taking us from Stanton through Winchcombe and eventually onto Cheltenham, where we caught the train home.

Cleeve Hill, Cotswold Way

The Cotswold Way is just gorgeous. It took us up over the rolling hills of this beautiful area of countryside, through golf courses and poppy fields, over hills past ancient structures, and past many, many sheep. We covered around twenty miles of the over 100 miles of trail on that Sunday, that started in brilliant sunshine before clouds rolled in. The trail is both interesting and beautiful through this part of the western Cotswolds.

The Cotswold Way From Stanton to Cheltenham

To plan this day’s journey, we used this hike planner and our trusty OS maps app. The Cotswold Way is mostly well-marked, but OS maps was helpful as usual when things seemed a little hairy.

Stanton to Winchcombe on the Cotswold Way

After a nice breakfast at the Old Post House, we set out on foot toward Cheltenham. This was going to be a long day of walking, but the sun was shining, the horses and cows were grazing and the flowers were in blooming splendor.

Field along the Cotswold Way, Stanton, Cotswold

The Cotswold Way

How to scare me on a countryside walk: cows and BULLS

Soon we passed by Stanway House, a Jacobean manor house. The manor is home to a water garden, which contains the largest water fountain in Britain. With many more miles to go, we didn’t have time to take a look, but the photos I’ve seen are stunning. The house and gardens are open to visitors during June, July and August.

Stanway House, The Cotswolds

We passed several groups of school children hiking along on what appeared to be a camping weekend. We climbed the first of our 1,000 foot ascents during this leg of the walk.

The Cotswold Way

The Cotswold Way from Stanton to Cheltenham

After climbing this first hill, we passed our first patch of poppies. The red flowers were so beautiful against the green fields and grey skies.

Poppies along the Cotswold Way

Just before lunch time, we reached Hailes Abbey. We had hours left of hiking so we didn’t stop into this English Heritage site, but we did walk around and snag a couple pictures! You can see the remains of the abbey from the trail, built in 1246. Pretty neat!

Hailes Abbey, The Cotswold Way

From the abbey, it was a short walk into Winchcombe, a quintessential stone Cotswolds village.


We arrived in Winchcombe at midday. By then the weather had turned to grey and rainy. We were lucky enough to stop during some showers that ended just before we got back onto the trail after a lovely meal.

Winchcombe, The Cotswolds

Layton’s Fish & Chips, pictured here, serves gluten-free fish and chips, but is closed on Sundays, tear!!

We stopped for lunch at Food Fanatics, which was a lovely deli and upscale grocery with delicious coffee. They were able to make all of their sandwiches on gluten-free bread, so I was a happy lady (and we got a gluten-free cheesecake brownie to share!). Two days of gluten-free sandwiches in the Cotswolds and a gluten-free toffee pudding. Success.

Gluten free sandwich at Food Fanatics, Winchcombe, Cotswolds

After fueling up, we got back in our gear and rain gear and walked back along the Cotswold Way.

Cotswold Way from Winchcombe to Cheltenham

The Cotswold Way twists and turns itself along the way from Winchcombe to Cheltenham. With more hills on this day of our hike, I was feeling much more tired after lunch. The twists and turns took us around versus straight on through to Cheltenham, which my tired feet may have wished it might. The views and sights were well worth the walking, though.

The trail takes you right by the entrance to Sudeley Castle, which we have heard from friends is just lovely, particularly the gardens in summertime. Near there we passed my favorite sheep of the day, who we affectionately named Pancake Sheep.

Pancake sheep, The Cotswold Way

Hello, Pancake!

The trail became more established with paving stones as we approached Belas Knap Long Barrow. Constructed in 3000 BC, it served as a burial ground and features a false entrance to the chambers in addition to the real entrance. You can peek inside, which is pretty cool!

The Belas Knapp Long Barrow, The Cotwolds

On this leg of the walk, we passed by several more poppy fields. And lots and lots more sheep!

Poppies along the Cotswold Way

Our final ascent, just before reaching Cheltenham, was to climb Cleeve Hill. This hill is the highest peak in the Cotswolds, looking over Chelteham from above at 1,083 feet.

The Cotswold Way, Cleeve Hill, Cheltenham

Almost there!

The trail winds around a golf course, which is so cool! The views from the green are spectacular.

The Cotswold Way, Cheltenham

We walked along, taking in the beautiful views as we went.

The Cotswold Way, CLeeve HIll, Cheltenham

After a ways, we split off from the Cotswold Way to descend into Cheltenham to catch the train back to London.

Cleeve Hill

The descent was interesting and perhaps less a trail as a dried up stream, but we made it down into the city with no trouble.

Cleeve Hill, Cotswold Way

We finally caught a cab about twenty minutes into our walk to the train station, making it just in time to catch a train that would help us get back to London after our direct train was canceled. We caught a train first to near Bristol, then switched to another that would take us into Paddington.

Getting up to stand again after the hour train ride to Paddington, I suddenly found I could barely walk for pain in my calf muscle! It was so strange. I hobbled along to the Tube and then to Pizza Express for dinner. The great Pizza Express would surely heal me.


They had run out of their normal gluten-free pizza bases, so I got two little ones. Obviously, two pizzas is better than just one pizza so I was a happy camper. Pizza and a well-earned glass of red wine to end a long and fabulous day on the trail!

After this training hike, we were less than two weeks out from our Swiss hiking adventure, coming to the blog next week!


Jenn is an American expat living in London, spending her time freelancing, traveling and writing on this here blog. Thank you for reading. Are you planning a trip here? Tell me your plans in the comments!

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  1. August 9, 2018 / 3:56 am

    Two pizzas are DEF better than one 😉 hehe. Love reading all your adventures. These are the memories you’ll share with grandbabies some day!! <3

    • Jenn
      August 9, 2018 / 7:14 am

      Pizza forever ❤️

  2. September 10, 2018 / 8:11 am

    My sister will agree with you about the cows. Love this account and hope to do some of the Cotswold way myself someone. Popped a link on my post about Walking in Winchcombe.

    • Jenn
      September 11, 2018 / 2:02 pm

      Hi, Sally! Thanks for stopping by and reading! You absolutely should, it is a lovely trail though challenging beyond Winchcombe. I enjoyed reading about your experience walking there and am totally jealous you grew up in such a beautiful area!

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