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United Kingdom
England
Yorkshire And The Humber
North Yorkshire
Ryedale

Upper Helmsley

The best running trails around Upper Helmsley

4.4

(32)

4,204

runners

269

runs

Jogging around Upper Helmsley offers access to varied yet accessible landscapes, making it suitable for a range of fitness levels. The region is characterized by a mix of agricultural fields, small woodlands, and paths along the River Derwent. Its generally flat to gently rolling terrain provides a pleasant environment for running.

Best jogging routes around Upper Helmsley

  • The most popular jogging route is Wilson's Plantation loop from Stamford Bridge, a 4.8 miles (7.7 km) trail that takes about 53…

Last updated: May 12, 2026

21

runners

#1.

Wilson's Plantation loop from Stamford Bridge

7.67km

00:53

10m

10m

Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Moderate

15

runners

Easy run. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Easy
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Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate

Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard

Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate
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Popular around Upper Helmsley

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Tips from the Community

Trev
July 2, 2025, Stamford Bridge and Battle of 1066 Site

Go into the village and visit the whiskyshop.

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This is the site of the Battle of Stamford Bridge on 25/09/1066, a turning point in English history. It was here that King Harold of England defeated the Viking King Harald Harada and Harold's own brother Tostig. This resulted in the end of the Viking era in England, such was the loss of life. Though from here, King Harold and his men had to march to Hastings on the south coast of England to meet William of Normandy who was challenging Harold's ascension to the throne. Harold's exhausted and much depleted men were defeated at the Battle of Hastings and Harold killed. This lead to the Norman Conquest of England. The Battle of Stamford Bridge is depicted in the Bayeux Tapestry. There are monuments to the Battle of Stamford Bridge in the village and on the site of battle at the end of Whiterose Drive.

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High Catton Hill 37.1m P21.6 (122ft) County of Yorkshire Definitive List Summit

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The field to the north east of the road is the site of the Battle of Stamford Bridge on 25/09/1066, a turning point in English history. It was here that King Harold of England defeated the Viking King Harald Harada and Harold's own brother Tostig. This resulted in the end of the Viking era in England, such was the loss of life. Though from here, King Harold and his men had to march to Hastings on the south coast of England to meet William of Normandy who was challenging Harold's ascension to the throne. Harold's exhausted and much depleted men were defeated at the Battle of Hastings and Harold killed. This lead to the Norman Conquest of England. The Battle of Stamford Bridge is depicted in the Bayeux Tapestry. There are monuments to the Battle of Stamford Bridge in the village and on the site of battle at the end of Whiterose Drive.

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Nice place to stop and enjoy the trees, perhaps have picnic etc.

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A bridge has crossed over the River Derwent in Stamford Bridge since the Roman times. Over the centuries, the bridge has been upgraded from a timber-framed bridge to stone during the 13th century. The bridge as we know it today was designed by Willam Etty in 1725. It is a Grade-II listed monument.

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Frequently Asked Questions

How many running routes are available in Upper Helmsley?

Upper Helmsley offers a wide variety of running routes, with over 290 trails to explore. These range from easy, leisurely jogs to more challenging distances, catering to all fitness levels.

What do other runners say about the trails in Upper Helmsley?

The running trails around Upper Helmsley are highly regarded by the komoot community, boasting an average rating of 4.5 stars from more than 30 reviews. Over 4,000 runners have used komoot to discover the varied terrain, often praising the peaceful woodlands and scenic riverside paths.

Are there easy running routes suitable for beginners in Upper Helmsley?

Yes, Upper Helmsley has a good selection of easy running routes, with 31 trails specifically rated as easy. A great option for beginners is the Running loop from Stamford Bridge, an easy 4.8 km path that offers a less strenuous outing on mostly paved surfaces.

Can I find shorter running routes, like 5k, in Upper Helmsley?

Absolutely. For a quick run, the Running loop from Stamford Bridge is an easy 4.8 km (approximately 3 miles) path, perfect for a 5k distance. It's ideal for those seeking a less strenuous outing on mostly paved surfaces.

Are there more challenging running trails for experienced runners?

Yes, for those seeking a greater challenge, Upper Helmsley features 36 difficult running routes. An example is the Wilson's Plantation loop from High Catton, which spans over 16.5 km and offers a more demanding experience through varied terrain.

Are the running routes in Upper Helmsley suitable for families?

Many of the routes in Upper Helmsley are suitable for families, especially those rated as easy or moderate. The generally flat to gently rolling terrain, combined with well-defined paths through agricultural fields and small woodlands, makes for an enjoyable outing. Consider shorter loops like the Running loop from Stamford Bridge for a family-friendly experience.

Can I bring my dog on the running trails in Upper Helmsley?

Generally, dogs are welcome on many of the public footpaths and trails around Upper Helmsley. The mix of agricultural fields and woodlands provides a great environment for running with your canine companion. However, always keep dogs under control, especially near livestock, and adhere to local signage regarding lead requirements.

Are there circular running routes around Upper Helmsley?

Yes, the majority of running routes in Upper Helmsley are circular, offering convenient starting and ending points. This allows you to explore the diverse landscapes, including woodlands like Wilson's Plantation and Town End Plantation, and riverside sections along the River Derwent, without retracing your steps.

What kind of scenery can I expect on the running routes?

Runners in Upper Helmsley can expect picturesque and refreshing scenery. The area is characterized by a charming mix of agricultural fields, small woodlands such as Wilson's Plantation and Town End Plantation, and peaceful paths along the River Derwent. These features provide a tranquil backdrop for your run.

Are there any interesting landmarks or attractions near the running routes?

While running, you'll primarily enjoy the natural beauty of the fields and woodlands. However, the wider region offers historical sites. For example, you can find highlights like Clifford's Tower and Kirkham Priory Ruins a short distance away, providing opportunities to explore local history after your run.

What are some popular running routes that feature woodlands?

Many routes incorporate the area's lovely woodlands. The Wilson's Plantation loop from Stamford Bridge is a popular 7.7 km trail that takes you through local woodlands and open fields. Another great option is the Town End Plantation loop from Stamford Bridge, a 9.8 km trail winding through farmland and smaller wooded areas.

Are there any running routes along the River Derwent?

Yes, the River Derwent offers peaceful and scenic sections for running. While specific routes are not detailed here, the region research indicates that paths along the River Derwent provide a tranquil atmosphere for outdoor exercise, often integrated into longer loops that combine riverside sections with field edges.

Most popular routes around Upper Helmsley

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