Short Days, Full Pints: Six Winter Routes Out of Kirkbymoorside

Winter walking around Kirkbymoorside is less about bagging summits and more about timing. The sun clocks off early, the field edges turn to brown soup, and the best views are often the ones you get from a pub window with your boots steaming under the table. The six routes below all start and finish in or near town, and each one ends at a specific pub with a specific reward. They are not heroic. They are the sort of walks you can do on a Saturday in November, a frosty Boxing Day, or a bright February morning when the moors have that tinny, washed-out light.

Take OS Explorer OL26, a headtorch, and a spare pair of socks. Check pub hours before you set off — winter opening can be shorter than the website suggests. And if the weather turns, turn back. The moors will still be there.

1. The Gillamoor Loop — 4.5 miles

Start in Market Place and head north on the Gillamoor road, picking up the field path past Kirkby Mills. It is a steady climb, but the reward is the view back over the town and, on a clear day, the white horse at Kilburn. The return drops through Keldholme, where the lane can be icy in the shade.

Pub: The Royal Oak, Gillamoor. Order: steak pie if it is on, and a pint of Black Sheep. Winter note: the last road section is unlit, so bring a headtorch.

2. Fadmoor and Douthwaite Dale — 5.5 miles

From the top of town, take the lane towards Fadmoor and loop west through Douthwaite Dale. This is proper winter walking: muddy gateways, low sun in your eyes, and the smell of woodsmoke from the farms. The dale is sheltered, which makes it a good choice when the wind is up on the moor.

Pub: The Plough Inn, Fadmoor. Order: soup of the day and a cheese sandwich. Winter note: some field edges are deep mud after rain; gaiters are not a fashion statement here.

3. Hutton-le-Hole via Keldholme — 6 miles

Follow the old lane to Keldholme, then field paths east to Hutton-le-Hole. The village is quieter in winter, and the steam from the beck looks good in cold air. There is a short road stretch near the end — keep left and wear something bright.

Pub: The Crown Inn, Hutton-le-Hole. Order: ham, egg and chips. Winter note: the museum may be closed, but the green and the beck are free.

4. Lastingham and Cauklass Bank — 7 miles

This one has a proper moor-edge feel. Head north over Cauklass Bank, with long views towards the Esk Valley, then drop into Lastingham. The church crypt is worth a look if it is open, and the village feels tucked away in the best possible sense.

Pub: The Black Swan, Lastingham. Order: a pint of bitter and the fish pie. Winter note: the bank can be exposed; turn back if the cloud drops.

5. Sinnington and the Seven — 5 miles

A gentler river-and-field walk south-east of town, following lanes and paths towards Sinnington. After heavy rain, the Seven can be high, so check the forecast and avoid the low-lying fields. This is a good route for a short winter day when you want distance without a big climb.

Pub: The Fox and Hounds, Sinnington. Order: Sunday roast if you have timed it right; otherwise a sandwich and a local ale. Winter note: the river path can flood, so have a road alternative in mind.

6. Helmsley via Riccal Dale — 8 miles

The longest of the six, and the one that feels most like a day out. Head south-west from town, follow the Riccal Dale paths, and arrive in Helmsley with time for a late lunch. You can catch the bus back or arrange a lift; either way, do not leave the return too late.

Pub: The Feathers, Helmsley. Order: a pint of Yorkshire ale and whatever is on the specials board. Winter note: this is a full-day walk in December — start by 9am and carry a flask.

Winter kit and pub etiquette

The essentials are simple: waterproof boots, warm layers, a map and compass, a headtorch, a flask, and a phone battery pack. Cash helps in pubs that prefer it. Muddy boots should come off at the door, and dogs are welcome in many bars but not all — ring ahead if you are bringing one. Most winter sunsets here arrive before 4pm in December, so plan to be off the high ground by 3pm.

The town-centre fallback

If the weather cancels everything, the King's Head Hotel in Kirkbymoorside is the obvious bolthole. It is warm, central, and close enough to the bus stop to make a sensible Plan B. Sometimes the best winter walk is the one you abandon for a pint.