We arrived in Chepstow without much of a plan. Laura and I, along with my sister, had no reservations for a place to stay, nothing we needed to do, and no clear objective other than to move on. For us, Chepstow was merely a launching point on our hike through the Welsh countryside. We chose it because it was well-situated, nothing more.

But quickly we realized Chepstow was more than just a way station. Our first eye-opening experience came while looking for a place to stay. Chepstow is only home to about 15,000 people, but we arrived during an event that left much of the town’s lodging full. We spent our first hour or so in town knocking doors of places advertising rooms for rent — most of them with a simple piece of paper taped to a window — until we finally arrived at the home of Jan and Glyn.

We had never met Jan and Glyn, of course, but they answered the door so warmly that we immediately felt welcome. They didn’t have a room set up for three people, but told us to wait while they ran next door to retrieve a futon cushion that they could set up on the floor.

The next morning, Glyn made us a traditional Welsh breakfast while telling us about his town and life. It was a casual, ordinary experience, but it broke down the chasm of outsider-ness that’s often a part of traveling to a foreign country.

Our time in Chepstow continued to exceed our expectations. At Glyn’s suggestion, we ate dinner at the friendly neighborhood pub. Later, we explored a tiny local history museum and meandered along a self-guided tour in the heart of the city.

But the crown jewel of the town was the castle. Chepstow Castle was begun in 1067 on the orders of one of William the Conquerer’s advisors.


Today, it looms, a semi-ruin, magnificently on the cliffs above the Wye River. Apparently, it’s also the oldest post-Roman stone fortification in Britain that is still standing, and has the oldest wooden castle doors in Europe (though they’re kept inside now).

Though the site is far smaller than better-known castles in big cities — the Tower of London, for example, or Edinburgh Castle — it’s far less curated. That means visitors are free to wander from chamber to chamber, or spend time quietly gazing out across the valley. We walked the ramparts at our own pace, while below children played on the grass as if it were an ordinary park. It wasn’t crowded, and given Chepstow’s size and relative draw, I doubt it’s ever close to the tourist circus at big city castles.


By the time we left the castle, and shortly thereafter Chepstow itself, we were falling in love. Though we hadn’t gone in with great expectations, we left reminded of how visiting smaller, off-the-beaten path places is often one of the best parts of traveling.

— Jim Dalrymple II


Written by Jim Dalrymple II

Urbanism and travel writer. Also a journalist covering the news.


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