4.5
(1801)
10,383
hikers
7
hikes
Family friendly hiking trails around Grassmoor, Hasland And Winswick traverse a landscape shaped by both agricultural land and reclaimed industrial sites. The area features a blend of farming and pasture land, interspersed with pockets of forestry. Former colliery sites have been transformed into recreational areas, offering varied habitats including hay meadows and woodlands. Several reservoirs and ponds contribute to the region's natural features.
Last updated: July 1, 2026
4.4
(16)
88
hikers
10.2km
02:39
70m
70m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.
16
hikers
7.83km
02:04
70m
70m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

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5.0
(1)
6
hikers
19.2km
05:06
190m
190m
Hard hike. Very good fitness required. Easily-accessible paths. Suitable for all skill levels.
5
hikers
5.34km
01:25
50m
50m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
4
hikers
14.2km
03:45
130m
130m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.
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Five Pits Trail Snowy Walk offers views over williamthorpe ponds
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looked incredible with the ponds frozen and the snow
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fishing ponds along the 5 pits trail, looked good when the pond was frozen over
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At either end of the Tom Hulatt Mile between Pilsley and Tibshelf, there are memorials that celebrate the life of the Derbyshire athlete who came 3rd in the historic race in which Roger Bannister ran the first sub-four-minute mile in 1954. Hulatt worked in coal mines at Holmewood and Williamthorpe, walking the four miles there from his home in Tibshelf and running back along the old railway line. He died aged 59 in 1990 and is buried in the village churchyard.
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Locko Plantation was once a slag heap for Pilsley Colliery.
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There has been a church at Tibshelf since the twelfth century though no trace remains of the original building. The oldest remaining part of the church is the tower which dates from the 15th century. Parts of the north aisle date from 1729. The chancel and south aisle date from 1910 after a fire destroyed that which had been built in the 18th century. In the church yard are the graves of six local men who died in World War 1 and three who died in World War 2, as well as a war memorial with names of the fallen from the village.
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Great for beginners and kids, outdoor gym & activities too.
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There are 5 family-friendly hiking trails in the Grassmoor, Hasland And Winswick area, ranging from easy strolls to more moderate adventures. These routes are carefully selected to be suitable for families looking to explore the local landscape.
Yes, the region offers routes suitable for prams and younger children. The Wolfie Pond loop from Tupton is an easy 6.2 km route with minimal elevation, making it a great choice for families with pushchairs. The Five Pits Trail, which runs through Grassmoor Country Park, also features level, surfaced tracks ideal for prams.
The trails in Grassmoor, Hasland And Winswick offer a mix of reclaimed industrial landscapes, woodlands, and water features. You can explore areas like Grassmoor Country Park, which was once a colliery, now transformed into a recreational space with ponds and diverse habitats. Nearby, the Pleasley Pit Colliery and Nature Reserve offers views and a glimpse into the area's heritage. The Miner Statue is another notable landmark.
Many of the trails in the Grassmoor, Hasland And Winswick area are dog-friendly, especially those on the Five Pits Trail and within Grassmoor Country Park. However, it's always recommended to keep dogs on a lead, especially near wildlife, livestock, or in designated nature reserve areas, and to clean up after them.
The region is enjoyable year-round. Spring brings beautiful bluebells to the woodlands around Linacre Reservoirs and new life to the nature reserves. Summer offers pleasant conditions for longer walks. Autumn showcases vibrant foliage, particularly in the wooded sections, and winter can provide crisp, quiet walks, though some paths might be muddy. Grassmoor Country Park and the Five Pits Trail, with their surfaced paths, are generally accessible in most weather conditions.
Yes, several routes are circular, making them convenient for family outings. For example, the Five Pits Trail – Adventure Bike Trail loop from Tupton is a moderate 10.2 km circular hike. Another option is the Adventure Bike Trail – Five Pits Trail loop from Tupton, which is a moderate 7.8 km circular route.
Parking is generally available at key access points for popular trails. For instance, Grassmoor Country Park, a central point for many family walks, has dedicated parking facilities. When planning your specific route, it's advisable to check the starting point for available parking options.
The area is highly rated by the komoot community, with an average score of 4.5 stars. Reviewers often praise the well-maintained paths, the blend of natural beauty and reclaimed industrial heritage, and the suitability of the trails for all ages, making them perfect for family adventures.
While specific establishments directly on the trails may be limited, the nearby villages of Grassmoor, Hasland, and Winswick, as well as the larger town of Chesterfield, offer a selection of family-friendly cafes and pubs where you can refuel after your hike. Grassmoor Country Park is a good starting point to find local amenities.
The longest family-friendly hike listed is the Adventure Bike Trail – View of the Five Pits Trail loop from Tupton, which covers a distance of 14.2 km. This moderate route offers a good challenge for families looking for a longer day out.
Public transport options, primarily bus services, connect the local villages and towns, including Grassmoor, Hasland, and Winswick. Some bus routes may have stops conveniently located near access points for trails like the Five Pits Trail and Grassmoor Country Park. It's recommended to check local bus schedules for the most up-to-date information.


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