Ask the Square First: Twelve Checks Before You Book a Kirkbymoorside Cottage

The photos do the persuading, don't they. Beams, a woodburner, a kitchen with a farmhouse sink, and somewhere in the corner of frame three, a slice of moorland that looks close enough to touch. Four minutes later you've paid a deposit on a cottage two streets back from the Market Place, and you're already planning the mornings.

Nothing wrong with that. But a week in a small Yorkshire market town is a slightly different proposition from a week in a resort, and most of the surprises people get here aren't unpleasant — they're just unplanned for. So before you book, or before you commit to something longer than a week, sit down with these twelve questions. They aren't a property survey. They're a reality check, and each one has a place in town where you can go and find the truthful answer.

The practical ones, which catch most people out

1. Can you arrive and leave without a car?

Yes, technically. The 128 runs between Pickering and Helmsley through the town, and it's a decent service by rural standards rather than a generous one — gaps of a couple of hours in the middle of the day, thin on Sundays, and nothing much after early evening. The seasonal moorland buses are a summer treat, not a year-round safety net. Test it properly: stand at the stop on the Market Place with a coffee and watch one go past that you weren't planning to catch. If the timetable makes you irritable rather than relaxed, book somewhere with a station.

2. Do you know what time the light goes?

In June, half past nine and still blue over the rooftops. In late November, dusk is settling by half four, and in the run-up to Christmas it's dark before four. Add a moor that hoards low cloud and a town that sits in a slight hollow, and winter afternoons here are short in a way that photographs never convey. The test: on any winter visit, walk up the Gillamoor road at three in the afternoon and see how much day is left. If you find that cosy rather than depressing, you'll be fine. If not, come in May.

3. Do you know which day the town actually works?

Wednesday is market day, and the square has a different pulse — stalls out, vans parked at angles, conversations happening across the street rather than on the pavement. Monday and Tuesday are quieter, some kitchens shut early in the week, and a few shops keep hours that suit their owners rather than their visitors. There's nothing wrong with any of it. It just means that a Tuesday-to-Tuesday booking is a different holiday from a Friday-to-Friday one, so check the days before you fix the dates. And always read the board on the door rather than the website.

The ones about noise, neighbours and being a guest

4. Can you sleep through a working town?

Deliveries to the shops start early. If the ringers are practising at All Saints, you'll hear the bells. There'll be a bin lorry, a tractor that seems to arrive from nowhere, and on the right evening, people leaving the pubs in good humour at closing time. None of it is rowdy; all of it is audible. If you need absolute silence to sleep, ask for a cottage off the square and at the back of the building.

5. Are you happy being a visitor in a place where people live?

This is the honest heart of it. Kirkbymoorside isn't a preserved village or a stage set — it's a small working town with a school, a doctor's surgery, a hardware shop that will sell you one screw, and a butcher who knows what you bought last time. The test is easy. Go into a shop, ask a genuinely stupid question about something, and see how you're treated. Then behave accordingly: don't block the pavement for a photograph, don't treat the square as a car park, and buy something.

The walking ones, because that's why you came

6. Do you actually enjoy walking uphill on wet grass?

A lot of moorland walking is exactly that: a gradient, a stile, a squelch, a view that's worth all three. If the answer is no, be honest about it. The old railway line out of town is flat, drained and lovely in any weather, and the lanes towards Sinnington and Wombleton are gentle without being dull. There's no shame in a week of level ambles — but do plan them, rather than discovering on day two that every route you fancied starts with a climb.

7. Will you drive twenty minutes for a view, or walk forty for a better one?

Both are legitimate. But the second is the thing this town is unusually good at. Kirkdale, a short valley just east of here, gives you a walk, a stream, a Saxon churchyard and one of the finest little minsters in the county, and it's reachable on foot from the square if you've got the legs and the daylight. Test the mood before you book: if the idea of a three-hour round trip on foot for a church and a view makes you smile, you're in the right place.

8. What's your plan for the day the moor disappears?

It happens, and often. Low cloud comes down, the tops go grey, the famous views become a wall of wet nothing, and anyone whose entire itinerary is ridge walking ends up cross in a holiday cottage. Have a bad-weather card up your sleeve: the valley walk, the church, a slow lunch, an afternoon in Helmsley or Pickering, a second pot of tea. The people who love this area in all seasons are the ones who've stopped treating weather as an interruption.

The social ones

9. Do you want a pub with a fire, or a pub with a following?

You've got choices on and around the square, and they're genuinely different from each other — one leans towards food in the evening, one towards conversation at the bar, one towards whatever's on the telly. Spend a midweek evening in two of them before you commit to a favourite for the week. And check the hours: several pubs here don't do food late, and a few keep short hours in the winter.

10. Are you a joiner?

If you are, small towns reward it enormously: quiz nights, church events, the allotments, the noticeboards by the shops that carry half the town's social life in photocopied form. If you're not, that's fine too — nobody will force a raffle ticket on you. But be aware that in a town this size, you will be greeted, and repeated, and eventually recognised. Some people find that the best part of the week.

And the two for anyone thinking longer term

11. Have you been here in February?

Not a sunny Saturday in June. A wet, grey, four-o'clock-dark Tuesday in February, with the wind coming across the square and nowhere open until five. If you're considering a move rather than a week, that's the day to test — and if you can walk home from the pub in it and still feel pleased with your decision, you've got your answer.

12. Do you want to be known, or left alone?

Because you'll be known. That's the trade here: a butcher who remembers your order, a neighbour who notices your gate is open, a town where the gossip travels faster than the bus. For plenty of people that's the whole point. For others it's a reason to book a fortnight rather than a mortgage.

None of these questions are meant to put you off. This is a generous, quietly stubborn little town in a beautiful corner of the moors, and a week here, properly planned, is hard to beat. Just book with your eyes open, pack a torch and a copy of the timetable, and let the square tell you the rest.