Running around Winterbourne Steepleton is one of the best ways to explore more of this region. To help you discover the most beautiful places to run, we’ve reviewed our full collection of routes around Winterbourne Steepleton—and are proud to present the best running trails. Click on any of the routes for more details and browse real tips and photos uploaded by other runners.

Last updated: December 4, 2025

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1. Portesham & The Valley of Stones loop — Dorset

10.4km

01:13

220m

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

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Moderate

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2. Foxholes Coppice – Loscombe Wood loop from Littlebredy

21.8km

02:40

410m

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

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Hard

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3. Tumulus – Tumulus loop from Portesham

13.1km

01:22

140m

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

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Moderate

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4. Corton Hill – Friar Wadden Hill loop from Martinstown

24.6km

02:52

450m

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

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Hard

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5. Hardy Monument loop from Littlebredy

37.2km

04:30

730m

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

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Hard

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Browse the best Running Trails & Routes in other regions.

Bincombe Long Bredy Poxwell Stanton St. Gabriel Frome St. Quintin Burton Bradstock Dorchester Toller Fratrum Frome Vauchurch Chilfrome Maiden Newton Littlebredy Kingston Russell Wraxall Cattistock Cerne Abbas Lyme Regis Chideock Nether Cerne Frampton Evershot Stinsford Bridport Broadmayne Batcombe Godmanstone Compton Valence Alton Pancras Nether Compton Puncknowle Wootton Fitzpaine Litton Cheney Melbury Sampford Hog Cliff National Nature Reserve Seaborough Melbury Osmond Winterbourne Abbas Catherston Leweston Wynford Eagle Toller Porcorum Over Compton Valley Of Stones National Nature Reserve Minterne Magna Winterborne Herringston Bradford Abbas Buckland Newton Crossways Allington Melbury Bubb Winterborne Monkton Burstock Abbotsbury Charmouth Owermoigne Castleton Sydling St. Nicholas Broadwindsor Whitcombe West Knighton Chickerell Mosterton Langton Herring Piddlehinton Leweston Swyre Fleet Woodsford East Chelborough Winterborne Came Up Cerne Bradford Peverell Hermitage Stockwood Symondsbury Portesham West Compton Poyntington Pilsdon Puddletown Trent Whitchurch Canonicorum North Poorton Powerstock Askerswell Tincleton Rampisham Hilfield Ryme Intrinseca West Chelborough Athelhampton Stratton Goathill Loders Stoke Abbott Tolpuddle West Stafford Bradpole South Perrott Lillington Sherborne Mapperton Shipton Gorge Caundle Marsh Hooke Warmwell Chedington Piddletrenthide Winterborne St. Martin Sandford Orcas Longburton Marshwood Chilcombe North Wootton Folke Cheselbourne Melcombe Horsey Beaminster Thornford Haydon Burleston Dewlish Holnest Leigh Bothenhampton Yetminster Osmington Holwell Bishop'S Caundle Chetnole Halstock Puddletown Forest Corscombe Clifton Maybank Bettiscombe Oborne Beer Hackett Thorncombe Purse Caundle Netherbury Charminster

The best running trails around Winterbourne Steepleton

1. Portesham & The Valley of Stones loop — Dorset

2. Foxholes Coppice – Loscombe Wood loop from Littlebredy

3. Tumulus – Tumulus loop from Portesham

4. Corton Hill – Friar Wadden Hill loop from Martinstown

5. Hardy Monument loop from Littlebredy

Other adventures around Winterbourne Steepleton

Most popular routes around Winterbourne Steepleton

Most popular attractions around Winterbourne Steepleton

Get inspired with the komoot mobile app

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