Weymouth is an administrative area within the county of Dorset and I think that it deserves to be a separate entity on CS (Dorset is far too large to be useful). Weymouth District is defined in OSM. Can this be added please?
Is this the Dorset, England - CityStrides you’re referring to?
There’s A Whole Thing™ about many places in England - Replace England's admin level 6 (and 8 in some cases) with admin level 10
The community is (as far as I remember) quite divided on the issue. A handful of people contact me about an area too large existing in CityStrides … I replace it with the smaller areas … A handful of other people contact me about an area too small existing in CityStrides 
If you’re a Supporter, you can zoom out a bit to see all fo England & enable the city border view (globe icon button on the map) … you’ll see areas with more space e.g. Dorset … and you’ll see areas with smaller borders e.g. Wells just a bit northwest from Dorset.
If you click the top left “Run” button here - overpass turbo - you can zoom in and click on the displayed cities to get a sense of what would replace Dorset (this includes your example Weymouth).
I’d urge you (and anyone else reading along who’s local) to click around on a few places and check to see if they all seem more representative of “city” (as loaded of a term as it is) … maybe Dorset feels more like a county (from my own US perspective) and places like Winterborne Stickland feel more relevant
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I think I usually consider this from the perspective of “What do you say when people ask you where you’re from?” … if you say “I’m from Dorset” then, we’re done here - apologies for the number of streets ahead of you 
And I realize this isn’t a perfect approach, either … from the more pedantic side of there being likely 0 people saying they’re from “Dorchester Town Council” as opposed to just Dorchester … and 
maybe people from Arne say they’re from Wareham … since this situation is definitely not a one-size-fits all, I’m just looking for the least worst option 
Thanks, I’ve continued the discussion in the original thread.
I don’t envy you trying to find a solution that works well enough for every one! Boundaries in UK are often ill defined using historical references to church parishes that make no sense today.
I live in Kingston and the other side of the road is Richmond. The boundary between the two Boroughs has changed a few times, it used to go through a block of flats, and even now it has an odd shape locally so that a school is kept within Kingston though logically it should be on the Richmond side of the border.
I could talk for many hours about borders but I’ll try not to do so here!
Richmond is another good example of how things change…
I’ve got Richmondshire in CityStrides, but it’s now marked as historic in OSM - Relation: ‪Richmondshire‬ (‪150871‬) | OpenStreetMap
Its replacement would be - similar to your Weymouth example - Richmond at admin level 10 Relation: ‪Richmond‬ (‪7759387‬) | OpenStreetMap
…I don’t see a neighboring Kingston though…
That Richmondshire you’ve shown is different to the Richmond adjacent to Kingston. It’s up in Yorkshire (northern England). Richmond and Kingston are two adjacent boroughs in outer, leafy London.
And then there’s an adjacent borough of Kingston (technically 'Royal Borough of Kingston upon Thames).
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Thanks Liz, you make a good point for people not familiar with London; while most London Boroughs were given brand new names when they were formed in 1965, e.g. Brent or Hillingdon, both Kingston upon Thames and Richmond upon Thames were given the name of their most prominent towns, which still annoys people living in other prominent towns, e.g. Twickenham (rugby!) in Richmond.
The Borough was created by merging the Metropolitan Boroughs of Kingston-upon-Thames, Malden and Coombe, and Surbiton. These areas were also composed of more than one population area, e.g. Surbiton contains Tolworth.
While places like Tolworth and Surbiton still exist today geographically (if I lived there I would use those place names) there are no administrative, post code or physical boundaries that define them. I would also know that I lived in Borough of Kingston because that’s where I pay my Council Tax!
Therefore having Royal Borough of Kingston upon Thames as a city in CS makes absolute sense and having it nested with London also makes sense as they merge seamlessly on the ground; on my regular monthly walk to a bar in West Hampstead I walk in 6 or 7 boroughs depending on the route.