Village stay in May, 2023

You might enjoy some time with HF Hoidays on one of their “gentle walking” breaks, such as this one in the Yorkshire Dales, near the village of Sedbergh,, a small market town.

https://www.hfholidays.co.uk/holidays-and-tours/gentle-walking-sedbergh-3

More opportunities at other HF Holidays locations, including two in the Lake District, or Isle of Wight, Northumberland, and others.
Also look at their special interest breaks, which have themes like art, photography, nature, etc.

We have enjoyed several short holidays with this group. The accommodations and meals are high quality, and the camaraderie of the other guests makes for an enjoyable experience.

I’ve stayed in charming villages in the Cotswalds, but the walking paths in May could be very muddy, and that’s not what I’d call easy.

Potentially much easier, with available public transportation, and lots of history as well, a few years ago, my husband and I walked the Hadrian’s Wall path. We completely crossed England, from west to east, coast to coast. You could stay in a village (or several), and not necessarily have to do the full route. We had a baggage transfer service deliver our bags to the next pre-determined B&B along the route, and slept in a different town each night, over a week and a half. The paths were well marked, and fairly easy to walk, although we wore hiking boots. The one challenging section, with some steep, hilly ascents and descents, was the popular part between Twice Brewed and Housesteads Fort. I believe there are buses, and also tour companies, that provide transportation in that area.

Over the past 1,900 years, parts of the ancient Roman wall that separated the civilized Roman Britain from the uncivilized Picts to the north (today’s civilized Scotland) have been torn down, with the pre-cut stones used to build homes, churches, and other buildings. Much of the wall remains standing centuries later, with remnants of Roman forts and milecastles still there to explore. Here are also several amazing museums along the way.

Carlisle, Brampton, Haltwhistle, Gisland, and Hexam, for starters, might all be worth considering. You wouldn’t have to do one night stands, but stay and explore the surrounding paths. Seeing a bit of Hadrian’s Wall could be a bonus.

Hadrians Wall path is great but not for the faint hearted as the middle section does have a lot of up and down work.... Also gateways and stiles can get very muddy, especially if there are cattle around to churn up the soil. I seem to remember Shield on the Hill just east of Haltwhistle was always particularly bad.

It is possible to break the walk up into sections and walk 'both ways' from a central point, but this is going to increase the mileage as you may have to walk a distance off the wall to reach you B&B accommodation. If planning to walk from end to end, with overnight stops, you do need to plan a baggage carrier as you won't want to be carrying all your belongings as you walk! The bus service Cyn is referring to is AD122 which runs every two hours from Greenhead to Hexham, following the line of the wall.

The Yorkshire Dales is a possible, basing yourself in places like Settle/Giggleswick, Horton in Ribblesdale, Hawes. There is plenty of walking from any of these without the need for using public transport.

On the South Western Railway line there are some lovely towns (the SWR Exeter-London route) with walking paths. Sherborne is a small town with an 8th century abbey and footpaths to the villages and hamlets nearby.
Crewkerne is somewhat similar, there is the Monarch's Way which is the escape route King Charles ii took. Castle Cary and Wells also fall along this path.
Both footpaths, from the bits I've walked, are not nearly as difficult as the Cotswold Way or Hadrian's Wall. However bring boots as they can be muddy.
The Monarch's Way starts all the way in Worcester and ends on the South coast and there are many more towns along it

Make it easy on yourself.

Enjoying walking in London’s Richmond Park. Isabella Planation should be lovely in May. So should Kew Gardens.

You can also stroll along the The Thames Path. There are benches to rest on and you’ll enjoy seeing rowers.

Lastly, the Regent’s canal path is enjoyable. Limehouse to Victoria park is pleasant or from Granary Square up to Camden Lock. Good strolls.

On my last trip i stayed with friends in Richmond. I took a 10 minute train ride from the Richmond Quadrant to Putney . Got off and walked 4 blocks to Putney Bridge and down to the river path.

Followed it all the way to the Hammersmith Bridge (its closed for renovation) and on a bit farther to a favorite pub, The Dove.

All of the above in London environs. Easy public transport. Just a thought. Richmond and Chiswick are lovely London Neighborhoods to explore.