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East Midlands
Derbyshire
North East Derbyshire

Grassmoor, Hasland And Winswick

The best family-friendly hikes and walks around Grassmoor, Hasland And Winswick

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.

Best family friendly hiking trails around Grassmoor, Hasland And Winswick

  • The most popular family friendly hiking route…

Last updated: July 1, 2026

4.4

(16)

88

hikers

#1.

Five Pits Trail – Adventure Bike Trail loop from New Tupton

10.2km

02:39

70m

70m

Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

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Moderate

Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

Moderate
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Hard hike. Very good fitness required. Easily-accessible paths. Suitable for all skill levels.

Hard

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy

Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

Moderate
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Tips from the Community

Chris Shannon
January 10, 2026, Five Pits Trail

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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Chris Shannon
December 31, 2025, Wolfie Pond

fishing ponds along the 5 pits trail, looked good when the pond was frozen over

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A pretty fishing pond situated on the Five Pits Trail.

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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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Stumpy Ed
February 19, 2024, Five Pits Trail

Great for beginners and kids, outdoor gym & activities too.

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Frequently Asked Questions

How many family-friendly hiking trails are available in Grassmoor, Hasland And Winswick?

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.

Are there any easy, pram-friendly walks in the area?

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.

What kind of natural features or landmarks can we expect to see on these family hikes?

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.

Are the family-friendly trails suitable for dogs?

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.

What is the best time of year to go hiking with family in this region?

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.

Are there any circular routes suitable for families?

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.

Where can we park when visiting the family-friendly trails?

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.

What do other hikers enjoy most about the family-friendly trails in Grassmoor, Hasland And Winswick?

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.

Are there any cafes or pubs near the family-friendly hiking routes?

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.

What is the longest family-friendly hike available?

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.

Can we reach the trails using public transport?

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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