Obviously this is a rhetorical question right now! Lockdown shows no signs of ending, we’re all on tenterhooks to see what the government does next, and there has been no real mention of tourism when talking about easing of restrictions (although bumbling Boris alluded to “a great British summer” last week – so that’s put the kiss of death on things – and the transport secretary has warned against anyone booking holidays right now, which is a kick in the teeth).

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As difficult as it is to remember, or even imagine, stuck as we are in the depths of lockdown 3 with no sign of improvement in the short term, there was a brief interlude last year when the country opened up a little bit and we could get out and about and actually go places.

During those halcyon days, and in between campervan trips, I suggested a UK mini break somewhere pretty in a nice B&B. Which is how we ended up in Chepstow.

Actually, that’s not entirely true. I suggested Ludlow. The husband has never been, and I haven’t been for many years. It has a river, and a castle, a good food scene and isn’t too far to drive. So I booked us a great room with a balcony and we were all set. Until I searched my emails to look for the check in time a few days before and found I hadn’t actually booked it at all. A quick phone call to the hotel confirmed there was no booking, and that I had royally screwed up.

One of the big differences between my husband and I is that he will throw the towel in and admit defeat, whereas I cling on to any hope long past the point it’s reasonable to do so. Throw in a situation where the mistake is on me, and I’m the most stubborn mule you can imagine. Ludlow was, by this point, pretty much fully booked so alternative accommodation was a no-no but I refused to just stay home and started looking for an alternative destination.

Which is how I came upon Chepstow.

It’s not really that different; it has a castle, a river, and it ends in “ow”. Almost identical no?

Two things really surprised us about Chepstow. One – it’s really steep. Really steep. From the river up into the town and then beyond is on an incline. One of the roads in the middle of the town is called Steep Street, and it really is a case of steep by name, steep by nature. Guess where we were staying? At the top of a really steep bit. More on that later.

The other thing we were surprised by was the really great food we ate, and how well my husband’s gluten intolerance was catered for on standard menus. We had two wonderful Italian meals; one at Una Vita and another at Panevino (where I tried beef carpaccio for the first time), and both were excellent.

So, what is there to do in Chepstow and the surrounding area?

Chepstow itself is rather pretty, with narrow lanes and boutique shops in addition to the usual UK high street offerings.

You can still see sections of the 14th century mediaeval town walls, although I’m sure the legacy Christmas decorations visible near the ramparts are from more recent times!

Chepstow is situated on the River Wye, and I had visions of idyllic river walks as the sun glistened on the flowing water. Unfortunately it was quite an overcast weekend, albeit warm, and the river was about as dull and murky as you can get. Not quite so picturesque!

The river walk doesn’t go along the banks of the river, but up and around the outskirts at height. The husband was having some back problems at the time, so rather than exacerbate them we gave that a swerve, and settled for a beer garden instead.

The most prominent building in Chepstow is obviously the castle. We almost didn’t get to see it, despite it being one of the main reasons for our visit, because ongoing Coronavirus restrictions meant booking a pre-timed arrival slot, which we didn’t do far enough in advance to get the time we wanted! So, prior to our visit, there was some time killing in a pub beer garden (not a real hardship, I know).

Now, there’s no way to say this without sounding like a dick, but limited visitor numbers really improves the overall experience as a tourist (I know it’s not good for the economy, etc, just looking for a silver lining). There were only a handful of people in there, even though it was sold out, which meant we could wander at leisure with no queues and no discomfort. We were able to easily read the information displays and get photographs without other people on!

The castle is obviously a ruin, but a lot of the structure is still in place and there’s evidence from it’s residential status hundreds of years ago.

How amazing is this bench, carved into the shape of the castle?

I love castles anyway, and Chepstow didn’t disappoint. Even better, it was free for us to get in thanks to our English Heritage membership, so happy days!

There’s lots of good stuff in the vicinity of Chepstow, including Tintern Abbey (I wanted to visit but it was closed – thanks Covid) and Clearwell Caves which were fully booked (thanks again Covid). The whole Wye Valley region is an Area of Outstanding Natural Beauty, so there are lots of beautiful walks if that’s your bag.

Where to stay

My tip would be to stay as close to the river area as possible. The hotel we were booked into was only about 3/4 mile away from the river, but as I mentioned it was on a super steep hill, so walking down was tough and walking back even tougher. After checking out the route on foot in the afternoon, we actually got a taxi to the restaurant on the first night! Being city people as we are we thought we’d just flag a cab down at the end of the night, but it took 45 minutes of calling local companies, an argument between ourselves and a huffy partial walk before we were able to get one. We checked out the next morning, and relocated to a B&B opposite the castle!

Eating and drinking

I’ve already mentioned the two great Italian restaurants we ate at; both of which I would highly recommend. There were also some cute independent cafes and restaurants we liked the look of that were unfortunately still closed post lockdown.

The Boat Inn is situated on the river and, when we visited, was only offering outdoor table service on both food and drinks, and doing a brisk trade in both.

The Three Tuns is right outside the castle and has an idyllic hidden away beer garden full of wooden tables and fairy lights; we spent a very pleasant time there having pre-castle refreshments and meeting up with friends who live locally we hadn’t seen in a while.

The Woodfield Arms is also opposite the castle; it’s a B&B with a restaurant and beautiful hidden away garden, but unfortunately it closed early for food and drinks on Sundays so we didn’t get chance to spend any time there, which is a shame.

Visiting the castle

At the time of writing this blog the castle is currently closed, as are all attractions in Wales. Who knows what the future will bring in terms of restrictions, bookings and tickets, but you can find all the information you need on the Cadw website.

Before I go, little bit of trivia, on one side of the bridge crossing the River Wye you’re in Chepstow, and therefore Wales, and on the other side you’re in Gloucestershire, and therefore England!

You literally cross from one country to another. Chepstow Bridge opened in July 2016, and at the time it was the third largest iron arch bridge in the world.

When lockdown 3 is over and the UK opens up again, would you consider a trip to Chepstow?

Thanks, as always, for reading. x