I first visited Rochester a couple of years ago, after a lifetime of passing through it on the train in between Faversham and London. My partner has lived in Rochester all of his life, and so although I cannot claim to be a local, I am blessed with a degree of insider knowledge.
Rochester is, to say the least, a very strange place. sitting right in the midst of the Medway, right on the river, it is an oasis of calm quite different from the surrounding areas (the high street directly adjoins that of Chatham, which some argue is the birthplace of the term 'chav' - and having been there, I'm prepared to admit there may be some truth to the claim). Far from being dragged down along with the areas which surround it, Rochester stands proud and defiant in the centre, as if perfectly preserved in a Dickensian story. Take a stroll past the beautiful castle and Cathedral, down the quiant high street or into one of the many coffee shops, bespoke restaurants or pubs (Rochester is rumoured to have the highest density of pubs per square mile in its centre in the whole country - although I don't know how you'd go about verifying that), and you're bound to fall instantly for its charm and elegant sophistication.
Although it is this very nature, which while at first charming, that can turn out to be the town's biggest downfall. If you want a place to eat and drink out, or to browse endless charity and antique shops, look no further. however, if you want anything practical - a supermarket perhaps, or a DIY store, or somewhere to buy clothes - then be prepared to travel at the very least over the river into Strood, or more likely into Chatham. Also there is no fast food outlet in the town (unless you count the newly opened Subway; the opening of which was highly controversial in itself as it was seen by many as damaging to the town's character), no cinema, bowling alley, pool hall (although some of the pubs have tables). However, it's important not to overstate the inconvenience - the transport links are very good (both locally and more far afield - into London or down to the coast), and are being improved all the time, especially as Rochester features as a stop on the new Southeastern Highspeed service into London. And the local buses are fairly regular and easy to use. Also walking into Strood or Chatham from central Rochester is a doddle in good weather. For those who drive the problems are even less - and Bluewater is just around the corner. Having said that, if you are stuck in Rochester for whatever reason - there is very little to do for fun except for eat and drink.
Which brings me to the second small problem I have with the town - because of the high density of all kinds of pubs, bars and restaurants, the population of the medway towns tends to flock there in droves on Friday and Saturday nights. Whilst this tends not to be a problem, it can on occassion be a little rough, with the police in regular attendance in the early hours of the morning. However - the problems are no worse here than any other large town - it may just seem that way because the town is usually so quaint and quiet, and whilst it might get a little rough occassionally, I have never felt myself to be in any danger.
So; that pretty much sums up my view of the town, I'll sign off by giving those who might be planning a visit to Rochester a couple of little tips for places to visit off the beaten track.
Shozna: Seriously good award winning Indian restaurant with two locations; one just over the river into Strood, and another just outside of central Rochester. Well worth a look even if Indian food isn't your favourite - there's something for everyone. Much better than any of the more obvious Indian restaurants on the high street, and just as reasonably priced. It's definitely where the locals eat!
The Man of Kent: bit of a local secret in the you'd NEVER find it unless you were looking. Charming pub full of character - really friendly staff and locals (although being a local myself I'm somewhat biased), more that 15 beers on tap including local ales and cider and continental lagers from Germany and Belgium, and loads more in the fridges. On John's Street by the (recently demolished) old police station.
I was born and bred in Rochester and over the years have of course seen many changes,not all for the better. It is hard to believe that Rochester is actually a city as there is no shopping area to speak of.The High Street is a strange mix of pleasant restuarants and cafes, second-hand and antiques shops, some scruffy empty shops amd a few other places. Rochester is blessed with its history,the lovely cathedral and wonderful castle and this is used to promote tourism combined with the Dickens connection. It is a good place to visit for these reasons and despite the criticism of the High Street, it's still not a bad place to amble along for a browse. Tourism was not really a big thing when I was a child here but now the local council seems to want to make as much money out of it as possible,which is only natural I suppose, but it would be good if the shopping area was tarted up and developed a bit.