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  4. Penn Street & Winchmore Hill

Penn Street & Winchmore Hill

Start:
Estimated Finish:
Amersham and District group logo.

Amersham & District Group

We are the Amersham & District Ramblers. We have walks most days in the lovely countryside of the Chiltern Hills. NO NEED TO PRE-BOOK WALKS, JUST TURN UP. FULL INFORMATION ON OUR WEBSITE www.amershamramblers.org.uk

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  • a library jam-packed with thousands of tried-and-tested routes
  • a welcome pack teeming with top tips plus our Walk magazine
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Overview

Starting from Car Park we go through Penn Wood and Common Wood and down to Penn Bottom. Return to Penn Street via Winchmore Hill. Mainly woodland and some open land with good views. Quite a few ups and downs but no stiles.

Saturday, 4 October 2025
Start time:
2:00 pm
Estimated finish time:
4:30 pm
Difficulty:
Moderate
Distance:
9.5km / 5.9mi
Ascent:
207.3m / 680ft
Type:
circular

There will be a short stop half way through walk. Very well behaved dog on short lead welcome.

 

Features

  • Car parking available

Starting point

Grid reference:
SU 92353 96150
Nearest postcode:
HP7 0PY
what3words:
passes.charmingly.estate
Start time:
2:00 pm

Holy Trinity Church Car Park, Penn Street. Follow driveway from the main road. Prompt departure.

Upcoming walks with Amersham & District Group

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Rickmansworth Aquadrome Walk

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Difficulty:
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Distance:
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Rickmansworth and Batchworth Heath

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Difficulty:
Leisurely
Distance:
4.5 miles
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Berkhamsted and Aldbury

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Difficulty:
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Distance:
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Penn Street & Surrounding Area

Start:

Difficulty:
Leisurely
Distance:
4.0 miles
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Stokenchurch slopes

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Difficulty:
Moderate
Distance:
6.0 miles
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Sarratt Chess Valley

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Difficulty:
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Distance:
4.0 miles
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Walk from Amersham

Start:

Difficulty:
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Distance:
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Pednor/The Hundridge Estate

Start:

Difficulty:
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Distance:
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The Lee/Swan Bottom

Start:

Difficulty:
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Distance:
4.0 miles
Trinity Church, Penn Street

Penn Street & Winchmore Hill

Start:

Difficulty:
Moderate
Distance:
5.9 miles
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Penn & Tylers Green Area

Start:

Difficulty:
Leisurely
Distance:
4.0 miles
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Ivy House round walk

Start:

Difficulty:
Moderate
Distance:
5.3 miles
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Hyde Heath/Little Missenden

Start:

Difficulty:
Leisurely
Distance:
4.0 miles
One non serious up hill

Wooburn Park

Start:

Difficulty:
Moderate
Distance:
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Aldbury

Start:

Difficulty:
Leisurely
Distance:
4.0 miles
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Bellingdon/Buckland Common

Start:

Difficulty:
Leisurely
Distance:
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Cookham

Start:

Difficulty:
Leisurely
Distance:
4.0 miles
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Flaunden down to the Chess River and back

Start:

Difficulty:
Leisurely
Distance:
4.5 miles
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Lane End to Fingest walkers Cafe for Tea!

Start:

Difficulty:
Moderate
Distance:
5.4 miles
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Whelpley Hill & Surrounding Area

Start:

Difficulty:
Leisurely
Distance:
4.0 miles
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Tring Park and Hastoe

Start:

Difficulty:
Leisurely
Distance:
3.6 miles
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Misbourne Valley

Start:

Difficulty:
Leisurely
Distance:
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Sarratt

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Difficulty:
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Distance:
4.0 miles
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Ashridge

Start:

Difficulty:
Leisurely
Distance:
4.0 miles
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Shardeloes/Mop End

Start:

Difficulty:
Leisurely
Distance:
4.3 miles
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Hyde Heath/South Heath

Start:

Difficulty:
Leisurely
Distance:
4.2 miles
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Downley and Bradenham

Start:

Difficulty:
Moderate
Distance:
5.6 miles
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Ashley Green to Hockeridge and Pancake Woods

Start:

Difficulty:
Leisurely
Distance:
4.0 miles
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Penn Street & Surrounding Area

Start:

Difficulty:
Leisurely
Distance:
4.0 miles
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Ashridge near Berkhamsted to Ivinghoe Common

Start:

Difficulty:
Leisurely
Distance:
4.0 miles

Join the Ramblers and enjoy

  • unlimited free access to 50,000 Ramblers group walks
  • a library jam-packed with thousands of tried-and-tested routes
  • a welcome pack teeming with top tips plus our Walk magazine
  • exclusive discounts from our partners
  • knowing your support is opening up more places to walk and helping more people discover the joy of walking
Join now for just £3.58 per month
Register for an account for FREE