DAY 9 – TUESDAY, MAY 12, 2026
Today was another early start. Continuing with our now well-established routine, our luggage was out by 8:30 AM, followed by a big breakfast at our inn while we made the major decision of the day. Our tour company offered two options for today’s walk, both ending in the same destination:
Choice 1: a challenging 12-mile route along The Cotswold Way with two major climbs and sweeping ridge-top views.
Choice 2: an easier 9-mile walk through the valley with far less climbing, but without the scenic overlooks.
If you know us, or have been following this trip, you already know which route we chose.
We headed out feeling energized and ready for the challenge. We also left promptly after breakfast because the route notes warned us there was exactly one lunch option along the way and they only served food from 12:00 to 2:00 PM. Based on our pace, we estimated it would take us four to five hours to get there, so there was definitely some extra motivation in our step.
As we left the town of Winchcombe, we passed the ruins of Hailes Abbey, a once-prominent monastery that was largely destroyed during Henry VIII’s dissolution of the monasteries in the 1500s. A short while later we climbed up to Cromwell’s Seat, a plateau where Thomas Cromwell, Henry VIII’s infamous right-hand man, is said to have watched the abbey’s destruction. History in England really has a way of casually appearing along a walking trail.
The pep in our steps started to fade as we reached the first major incline, a climb of roughly 900 feet. Still, we steadily pushed upward through beautiful rolling fields, quiet pastures, and plenty of sheep for company.
With lunch still firmly on our minds, we continued on as the trail gently descended into the hamlet of Stanway, home to a remarkable Jacobean manor house that has reportedly only changed family ownership once in more than 1,300 years. About a mile farther down the trail we reached Stanton, our planned lunch stop.
Unfortunately, there was one final obstacle: the restaurant sat at the top of yet another hill.
We arrived at 1:10 PM feeling triumphant, hungry, and very ready to sit down. But when we stepped inside, the lone and very overwhelmed waiter informed us they could not accommodate any more lunch guests.
Not exactly the ending we had envisioned.
So, slightly defeated, we pulled out the protein bars we had thankfully packed and headed back to the trail. It was at about this moment we discovered we were beginning climb ascent number two and this one was steeper than the first.
Somewhere in the middle of that rocky, wooded ascent, surrounded by trees and heavy breathing, we started to question our choice. But after shedding a couple of layers and a large amount of effort, we reached the high point of the day at 973 feet and were rewarded with beautiful panoramic views across the countryside.
Thankfully, the remaining miles were mostly downhill as we wandered through more fields and pastures filled with cows, sheep, and horses. And after passing through our 49th gate of the day, yes, we counted, we finally arrived in the village of Broadway.
With the sun shining on the picturesque town center, we immediately agreed that Broadway was probably our favorite Cotswolds village so far. Since lunch had never materialized, our first priority was finding a tea room where we could gratefully sit down and enjoy an afternoon cream tea. We did manage to stop for a couple of postcards on the way to the hotel, but by that point our enthusiasm for additional sightseeing had faded right along with our leg strength.
Back at the hotel, we peeled off our hiking boots, stretched, showered, and enjoyed a few precious minutes of doing absolutely nothing.
Then it was time for dinner.
We’ve been especially grateful that our friend Bob, who had originally planned to join us on this trip, made dinner reservations for us throughout the Cotswolds. Most of them have been right at the hotels where we are staying, which after days like this has felt like a brilliant strategy.
Tonight’s dinner did not disappoint. A gin and tonic and a delicious meal felt very well earned after twelve miles and two major climbs. We were seated next to a friendly older couple who struck up a conversation after hearing our American accents. They shared that they had both held prominent federal government positions in Washington, DC, before retiring to Palm Beach, Florida. For the past 25 years they’ve spent two to three months every summer in the Cotswolds and prefer crossing the Atlantic by ship rather than flying. It was fascinating hearing their stories and honestly, a welcome distraction from our increasingly sore muscles.
The night ended with a hot bath for Karen and absolutely no trouble falling asleep.
Hammond Adventures 