Looking for the best cycling routes around Winterborne Monkton? On this page, we bring you the best bike rides around Winterborne Monkton so you can just get out and go. All you’ve got to do is choose your route!

Last updated: October 20, 2025

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1. Around Portland loop from Dorchester

61.6km

04:11

760m

Expert bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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2. Dorchester and West Knighton loop - Dorset

19.4km

01:15

190m

Intermediate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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3. Beaminster, Bridport & Burton Bradstock loop from Dorchester

87.3km

06:04

1,020m

Expert bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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4. The Frome Valley and Cerne Abbas loop from Dorchester

37.2km

02:39

490m

Expert bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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5. Hardy Monument – View from Crow Hill loop from Upwey

40.5km

02:45

580m

Expert bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Browse the best Cycling routes in other regions.

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

The best cycling routes around Winterborne Monkton

1. Around Portland loop from Dorchester

2. Dorchester and West Knighton loop - Dorset

3. Beaminster, Bridport & Burton Bradstock loop from Dorchester

4. The Frome Valley and Cerne Abbas loop from Dorchester

5. Hardy Monument – View from Crow Hill loop from Upwey

Most popular routes around Winterborne Monkton

Most popular attractions around Winterborne Monkton

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