September 2026 in North Yorkshire: A Hiker's Guide to Fairs, Walks and Festivals

Plan your walking trip around these real events, with practical advice on where to stay and how to get there.

Richmond and the Dales: Walking Festivals and Market Days

The Richmond Walking and Book Festival typically runs in late September, with guided walks ranging from 5 to 15 miles across Swaledale and Wensleydale. Most walks start from Richmond Market Place, where you can also browse the Saturday market. If you're based in Richmond, you can walk directly from your hotel; otherwise, the town is a 30-minute drive from Darlington station, which has direct trains from London King's Cross. Book accommodation early, as the festival draws crowds. For a quieter base, consider Reeth or Leyburn, both within a 20-minute drive.

The Dales Countryside Museum in Hawes hosts occasional guided walks, and the Hawes Tuesday market is a good place to stock up on local cheese and pies for a picnic. The Pennine Way passes through Hawes, so you can join a section without a car. The Herriot Way, a 52-mile circular route, also passes through the town. If you're hiking in September, expect mild days (15-18°C) but bring waterproofs; rainfall averages around 80mm for the month. Mid-September is ideal: schools are back, but the weather is still pleasant.

Coastal North Yorkshire: Festivals and Cliff Walks

Whitby's bi-annual Goth Weekend falls in late October, not September, but the town still buzzes in early September with the Whitby Regatta (usually mid-August) and the Whitby Walking Festival, which typically runs in September with routes along the Cleveland Way. The festival offers walks from 3 to 20 miles, including a popular 13-mile stretch from Whitby to Robin Hood's Bay. If you're staying in Whitby, book a hotel near the harbour or West Cliff for easy access to the start points. Parking is limited, so a hotel with parking is worth the extra cost.

Scarborough and Filey also host walking events. The Filey Folk Festival, usually in early September, is not hiking-focused but offers a lively base for coastal walks. The Cleveland Way National Trail runs for 109 miles from Helmsley to Filey, and September is one of the best months to tackle a section: the path is quieter, and the sea views are clear. For a challenging day, try the 9-mile stretch from Saltburn to Staithes, with steep climbs and dramatic cliffs. Stay in Staithes or Saltburn; both have small hotels and B&Bs that fill up quickly on weekends.

Moorland Events and Practical Logistics

The North York Moors host the annual Danby Show in early September, a traditional agricultural show with sheepdog trials and produce stalls. It's not a walking event, but it's a great way to experience local culture, and you can combine it with a walk on Danby Beacon or the Esk Valley Walk. The show is held at Danby, about 15 miles from Whitby. If you're staying in Pickering or Helmsley, it's a 30-minute drive. Accommodation in Helmsley is particularly convenient for both the show and the southern moors, with the Cleveland Way passing through the town.

For transport, the North Yorkshire Moors Railway runs steam trains from Pickering to Whitby, which is a scenic way to link walks. A day rover ticket allows you to hop on and off. Buses in the Dales are sparse; the 875 service from Wakefield to Richmond runs infrequently, so a car is often necessary. September is harvest season, so expect some farm traffic on narrow lanes. Book hotels with free cancellation in case of weather. The partner's site shows high demand for Whitby and York; if you're flexible, consider Malton or Thirsk as cheaper bases within 30 minutes of the moors.

Where to Book and What to Skip

For the Richmond festival, I'd book a hotel in Richmond town centre, ideally near the market square, so you can walk to the start points. The King's Head Hotel and the Richmond Arms are reliable, but they book up months in advance. For coastal walks, Whitby's YHA and the Angel Hotel offer good value, but check for minimum stays. If you're hiking the Cleveland Way, consider a luggage transfer service; several local companies operate along the route. Avoid staying in Scarborough if you want quick access to the moors; it's a 45-minute drive to Pickering.

Skip the big hotels in York if your focus is hiking; York is a 45-minute drive from the moors and parking is expensive. Instead, base yourself in Helmsley, Pickering or Richmond. For a splurge, the Feversham Arms in Helmsley is a comfortable post-walk treat. Budget travellers should look at independent hostels in Malton or Osmotherley. In September, mid-week rates are lower, and you'll have quieter trails. Book by July for the best choice, especially if your trip coincides with the Richmond Walking Festival. And always carry a paper map; phone signal is patchy in the dales.

Questions, answered

What are the best months for hiking in North Yorkshire?

May, June and September offer the best balance of weather and fewer crowds. July and August are busier, especially in Whitby and York. September often has stable weather and harvest scenery.

Do I need a car for North Yorkshire walking festivals?

Yes, for most events. Public transport is limited in the Dales and moors. However, the North Yorkshire Moors Railway connects Pickering and Whitby, useful for linear walks.

Where should I stay for the Richmond Walking Festival?

Book a hotel in Richmond town centre for walkable access to start points. Alternatively, Reeth or Leyburn are within 20 minutes by car and offer quieter settings.

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