Best castle ruins between London, Cheltenham, Shrewsbury?

I recommend visiting Ludlow Castle. This is on the way to Shrewsbury, and is a vast ruin that you can walk around. See: https://www.ludlowcastle.com/. The town of Ludlow is one of the most attractive market towns in England with some excellent restaurants. However, it seems to attract few tourists and is therefore rarely crowded. Just over the border in Wales is Powis Castle. This is a cross between a castle and a stately home, with a superb museum of some of the prizes that Robery Clive looted from India. See https://www.nationaltrust.org.uk/powis-castle-and-garden.

Have a great time.

Look on the English Heritage UK web site. They have a list with photos of most of the Castles with public access. They have a Pass available. They also have Abbeys and other Historic sites. Also check the National Trust UK site for other great ideas. They have Touring Pass. I enjoyed the walled town of Chester as a great place to stay. The kids will have a great time running along the Walls. The foundation is from the time of the Roman Regiment XX. The town has timbered houses in the Tudor style. The shopping Rows are Famous. We have stayed there twice and would go back again.

The foodies had discovered Ludlow when I was there in August 2017. Chester is larger and is worth a longer visit, I think, but it's north of Shrewsbury.

Kenilworth is on the way, sort of. Warwick is just down the road from there but the problem is that it isn't ruined.

Shrewsbury has one, but that isn't ruined either. Of course London has two - one called the Tower of London has fabulous battlement walks (just did that walk again last week) and more towers than you can count but only one of the towers is ruined (near the White Tower), but the problem is that it is in daily use - and the other called Windsor Castle is still a Royal residence and not at all ruined.

You sure that a non-ruined one would be no good?

I’m not going to talk about ruins but your assumption that November weather will be cold, rainy and dark.

I travel to London quite often in November. Yes Day light starts to disappear around 3:30pm and it can be in the 40’s but not always. It might rain but it shouldn’t be more than an occasional drizzle and not an every day all day affair.

In my experience you’ll also experience clear blue skies and sunshine.

Dress in layers and be pleased the hordes won’t be as large as what you’d find in summer months.

Definitely Ludlow if you’re going to be in Shrewsbury. A gorgeous town with excellent castle ruins. The perfect level of ruined, as well - I mean enough of the structure still stands so you can climb to the top of the tower for great views and the walls are still standing but nonetheless ruined enough to be romantic.

Chester is just over 40 miles north of Shrewsbury or 70 miles north of Ludlow and 47 miles to Conwy.

Here is a good round trip day tour from Cheltenham. Click the link for a map of the area:> https://www.google.co.uk/maps/@51.7366828,-2.437324,40490m/data=!3m1!1e3!5m1!1e1

Leave Cheltenham & head SW skirting Gloucester on A40 and then take A48 to CHEPSTOW - see the CASTLE. (Local road network is complicates with one way streets - zoom down and check it out). Then take A466 going north. If you take the minor road signposted ‘Wyndcliff’ on the first bend after St.Arvans - park in parking area on R just before sharp bend to L. Walk for 17 minutes up the zig zag track going uphill through the woods. Where it levels off - walk a few paces to right and you will come to the ‘Eagles Nest’ viewing platform over the Wye Valley. Then, return to car & continue up A466 to TINTERN ABBEY (ruin).

After Tintern, proceed N up the A466 following the river Wye. Look on the map - can you see ‘Area of Outstanding Natural Beauty’? If you head there, you will come to the YAT ROCK car park and the short walk to the VIEWPOINT. (Zoom map to see). After that, proceed in a loop out of the car park & and you can either head straight back to Cheltenham via A4136 or proceed down the hill (which is steep & very narrow) to Goodrich & Ross before going back to Cheltenham.

Also consider as day trip from Cheltenham to Cardiff - which has a Castle with a Norman keep plus later Victorian additions. If driving to Cardiff, it is best to use the M5 towards Bristol and then take the M4 over the Severn Bridge. (The section around Newport often jams up - so, you may wish to take the train - which would also avoid you having to find parking in central Cardiff - which has a complicated traffic system whilst the main shopping streets are pedestrian only zones). Trains = www.nationalrail.co.uk
(If you have time, you may wish to purchase in Cardiff, another return ticket to Caerphilly - which is about a 20 minute journey and has a huge medieval castle surrounded by a moat). http://cadw.gov.wales/daysout/caerphilly-castle/?lang=en
https://www.cardiffcastle.com

If driving from Cheltenham to Shrewsbury, Eastnor Castle (Victorian) is almost on the route - as is Lower Brockhampton Hall (near Bromyard). As others have mentioned - LUDLOW is worth a visit but 1 mile N of Ludlow is Stokesay Castle = a fortified Manor House.https://eastnorcastle.com
https://www.nationaltrust.org.uk/brockhampton-estate/features/discover-the-manor-house
https://www.english-heritage.org.uk/visit/places/stokesay-castle/

From Shrewsbury, as has been mentioned - Powis Castle is good. Also consider a day trip to Chester - which could be done by train or car.https://www.visitcheshire.com/chester
(If driving, consider a short detour to see:>https://www.pontcysyllte-aqueduct.co.uk).

Thanks for the wonderful suggestions- I appreciate it so much!

Not to worry, @Nigel- I’m sure we will take in some non-ruined castles! :) thanks for the ideas.

And @Claudia, I don’t expect it to be too dark or wet for fun- but I know folks often like to warn tourists who travel in off season that it must be planned for, so I wanted folks to be reassured that we are hardy! :)

And as for the detailed instructions - goodness! Thank you!

Once we have itinerary worked out we will be sure to report back! Cheers!

OP Update! We had nine magical days in England (with a quick stop in southern Wales). I was right that adding northern Wales would be too much, and I'm glad I talked myself out of it.

Cheltenham/Cotswolds: We went to the ruins of Hailes Abbey, but it was already closed for the season. However, we were able to observe over the fence from fairly close, and it was interesting. There's also a tiny 11th century church immediately next door that was open - that ended up being a highlight of our day.

Avebury/Silbury Hill/W Kennet Long Barrow: We did this as a day trip from Cheltenham. Totally do-able, even including an extended walk around all of the Avebury stones and a cream tea at the Trust cafe. We walked up to the long barrow and, if you go to Avebury, DO NOT miss this! It was a beautiful and easy stroll up the hill with gorgeous views and a chance to go inside a portion of a Stone Age burial chamber. Absolute trip highlight.

Tintern Abbey: Absolutely breathtaking. We spent 3 hours or so exploring the ruins, including the excellent plumbing still visible. This was the 8yo's favorite (and probably mine too). We ate tea at the little tearoom right next door, but then realized there was a whole little village about half a mile beyond that probably had better options.

Ludlow Castle: Fantastic. We tried to do this after Tintern, but we spent too much time there and then the castle was closed by the time we got to Ludlow. We unanimously decided it looked cool enough to go back to on our way out of Shrewsbury though, and we weren't disappointed. So many nooks and crooks and excellent "poop chambers" (as my 8yo called them - garderobe to others). Definitely buy the 1pound guide on your way in - we bought it on the way out and wished we had had it earlier.

Shrewsbury Castle: This was closed on the day we were in town! I should have read ahead. And you can only see small portions of the castle from outside it; it was not terribly interesting, sadly. Next time! :)

We did also do the Tower of London after all of this. It was super - but for us, hardly anything could compare with being able to walk around and in and touch the stones of Ludlow and Tintern Abbey. In short, a fabulous trip.

Thanks for all the excellent advice! It' was so appreciated.

Many thanks for coming back. It is always worthwhile to hear whether or not the suggestions made were good or bad. I note that you enjoyed in particular Tintern Abbey - which was one off my suggestions. Many times I have seen Glastonbury mentioned as a potential place to visit by Americans on this forum. I reckon that Tintern Abbey is a better ruin to visit and is under an hour’s drive from Bath - which is understandably one of the favourite places to visit outside of London.

Yes, it is quite a way from Tintern up to Ludlow - that is why I suggested going to the Yat Rock viewpoint before heading back to Cheltenham.

Thank you for sharing. So pleased you had a great few days of exploration!

Thank you for coming back and giving us a trip report.
It's always nice to hear from people who have gotten advice here, and had an enjoyable trip because of it.
So glad you had a good time!

I'm glad you came back with a report.

Never enough time is there?

Yep the W.K.Long Barrow is a beauty. That was our 2d day in the UK after arriving at a friend's in Shrivenham, Wiltshire. A drive to Avebury, awesome. Silbury Hill, amazing and bewildering. Then a walk through a cornfield up to the Long Barrow. That is a pretty special don't you think?