Outdoor Activities in Chesterfield

Cuckoo Way

30.4 km · 6h 45m · Challenging

Cuckoo Way · 0.5 mi

Trans-Pennine Trail (Staveley to Chesterfield spur)

8.7 km · 1h 56m · Moderate

Trans-Pennine Trail (Staveley to Chesterfield spur) · 0.5 mi

Trans-Pennine Trail (Staveley to Chesterfield spur - alternative route)

7.6 km · 1h 42m · Easy

Trans-Pennine Trail (Staveley to Chesterfield spur - alternative route) · 0.8 mi

North Chesterfield Way

14.2 km · 3h 10m · Moderate

North Chesterfield Way · 1.1 mi

Drone Valley Way

4.3 km · 57m · Easy

Drone Valley Way · 2.3 mi

Whittington and the Handleys

7.7 km · 1h 43m · Easy

Whittington and the Handleys · 2.7 mi

Poolsbrook parkrun

Saturdays

Poolsbrook · 2.9 mi

Linacre and Cordwell Valleys Circular Walk

18.4 km · 4h 6m · Challenging

Linacre and Cordwell Valleys Circular Walk · 3.6 mi

Frith wood, Summerley and Unstone

3.7 km · 49m · Easy

Frith wood, Summerley and Unstone · 3.9 mi

Round Holmesfield Walk

4.8 km · 1h 4m · Easy

Round Holmesfield Walk · 4.0 mi

Five Pits Trail

15.4 km · 3h 25m · Moderate

Five Pits Trail · 4.3 mi

Chesterfield Round Walk

52.6 km · 11h 41m · Challenging

Chesterfield Round Walk · 4.4 mi

A Walk On The Wild Side

8.4 km · 1h 52m · Moderate

A Walk On The Wild Side · 4.8 mi

Barlborough Heritage Trail

1.6 km · 21m · Easy

Barlborough Heritage Trail · 4.9 mi

The Chaffinch Trail

1.1 km · 14m · Easy

The Chaffinch Trail · 4.9 mi

North Wingfield Walk

4.6 km · 1h 2m · Easy

North Wingfield Walk · 5.3 mi

The Miners Way

2.1 km · 29m · Easy

The Miners Way · 5.3 mi

South Chesterfield Way

15.5 km · 3h 27m · Moderate

South Chesterfield Way · 5.7 mi

Dronfield Rotary Walk

17.1 km · 3h 48m · Challenging

Dronfield Rotary Walk · 5.9 mi

Peak District Boundary Walk Stage 11

16.6 km · 3h 41m · Challenging

Peak District Boundary Walk Stage 11 · 6.1 mi

Astwith Walk

7.6 km · 1h 42m · Easy

Astwith Walk · 6.1 mi

The Sculpture Trail, Hardwick

4.9 km · 1h 5m · Easy

The Sculpture Trail, Hardwick · 6.2 mi

Graves parkrun

Saturdays

Graves · 6.5 mi

The Miller's Walk, Hardwick

2.7 km · 36m · Easy

The Miller's Walk, Hardwick · 6.7 mi

The Welly Walk, Hardwick

5.3 km · 1h 10m · Easy

The Welly Walk, Hardwick · 6.7 mi

Pilsley Walk

5.0 km · 1h 7m · Easy

Pilsley Walk · 6.8 mi

Trans-Pennine Trail (Beighton to Staveley spur)

7.4 km · 1h 38m · Easy

Trans-Pennine Trail (Beighton to Staveley spur) · 7.1 mi

Millhouses parkrun

Saturdays

Millhouses · 7.1 mi

The Oak Walk, Hardwick

6.3 km · 1h 24m · Easy

The Oak Walk, Hardwick · 7.4 mi

River Sheaf Walk

8.6 km · 1h 54m · Moderate

River Sheaf Walk · 7.5 mi

GHB Ward Walk

17.6 km · 3h 55m · Challenging

GHB Ward Walk · 7.5 mi

Rother Valley parkrun

Saturdays

Rother Valley · 7.5 mi

Tibshelf Walk

4.6 km · 1h 2m · Easy

Tibshelf Walk · 7.8 mi

Frogatt, Curbar and White Edge Red Deer Circular Walk, Longshaw Estate

9.7 km · 2h 9m · Moderate

Frogatt, Curbar and White Edge Red Deer Circular Walk, Longshaw Estate · 8.0 mi

Sheffield Castle parkrun

Saturdays

Sheffield Castle · 8.1 mi

Rotherham Ring

4.5 km · 1h 0m · Easy

Rotherham Ring · 8.2 mi

Sheffield Round Walk

24.2 km · 5h 23m · Challenging

Sheffield Round Walk · 8.2 mi

Peak District Boundary Walk Stage 12

10.3 km · 2h 17m · Moderate

Peak District Boundary Walk Stage 12 · 8.3 mi

Derwent Valley Heritage Way

83.3 km · 18h 31m · Challenging

Derwent Valley Heritage Way · 8.5 mi

Blue Route, Longshaw Estate

5.0 km · 1h 7m · Easy

Blue Route, Longshaw Estate · 8.5 mi

Norfolk Heritage Walk

4.3 km · 57m · Easy

Norfolk Heritage Walk · 8.6 mi

Summer Holiday Activities – Tudor Cheer Week

Sheffield Manor Lodge · 8.6 mi

Summer Holiday Activities – Pesky Pirates Week

Sheffield Manor Lodge · 8.6 mi

Skegby Trail

2.5 km · 33m · Easy

Skegby Trail · 8.7 mi

Archaeological Way (old route)

23.2 km · 5h 10m · Challenging

Archaeological Way (old route) · 8.8 mi

Archaeological Way

9.2 km · 2h 2m · Moderate

Archaeological Way · 8.9 mi

Silverhill Trail

6.2 km · 1h 23m · Easy

Silverhill Trail · 8.9 mi

Views and Woodlands Walk at Longshaw, Longshaw Estate

9.2 km · 2h 3m · Moderate

Views and Woodlands Walk at Longshaw, Longshaw Estate · 8.9 mi

Orange Route, Longshaw Estate

3.3 km · 44m · Easy

Orange Route, Longshaw Estate · 8.9 mi

2026 Peak District Highland Games

Matlock Farm Park