Chester City Walls

Wrapping right around the heart of Chester, the Chester City Walls are one of those rare things that actually live up to the hype. They're the oldest, longest, and most complete city walls in Britain, with parts dating back nearly 2,000 years — and you can walk almost the entire circuit with your dog. The full loop is roughly 2 miles, taking about an hour at a relaxed pace, though realistically you'll stop plenty for the Eastgate Clock, medieval towers, river views, and constant little glimpses down into the city.

It's elevated most of the way, which gives you that slightly different perspective on Chester — rooftops, streets, and snippets of history all stitched together as you go. You can dip on and off at different points too, so it works whether you're committing to the full loop or just doing sections between coffee stops. Some sections are narrow with drops, so it's one for steady walking rather than full zoomies.

For dogs, it's one of the best city walks going. They're welcome to join you on the walls, which isn't always the case in other historic cities, making it a proper shared experience rather than a compromise.