Unexpected Essex

Episode 5: The Highwayman

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Summary

On this episode of Unexpected Essex, your host Eri Berry deep dives into the murky world of 18th century highway robbery. Today, we answer the question: just who was Dick Turpin, how was he connected to Essex, and exactly what was the real deal with highwaymen?

This episode explores the life of highwayman Dick Turpin, the circumstances of his eventual execution, and how society came to romanticise the figure of the gentleman highwayman in popular culture. Turpin was born in Hempstead, a small village in the north west of Essex. Initially working as a butcher, it isn’t long before he’s drawn into a shady world of poaching, robbery, and even murder.

Key Names and Places

Dick Turpin, Hempstead, Epping Forest, York, London, Thaxted, Waltham Forest, Lincolnshire

Transcript

Ep 5 – The HighwaymanDownload

Sources and Further Reading

Book: Dick Turpin: The Myth of the English Highwayman by James Sharpe (Profile Books, 2004) – An examination of how an 18th-century criminal was transformed into the legendary, romanticized highwayman of British folklore.

DISCLAIMER

While I do my best to bring you accurate, well-researched content, I’m only human! If you spot a mistake, have a correction, or want to share additional context, please feel free to reach out via email at unexpectedessex@gmail.com.

Image Attribution:

Episode Images:

Image:Source Name:Source URL:Licence Type:Attribution:Date Downloaded:
01 Dick Turpin.jpgWikimedia Commonshttps://commons.wikimedia.org/wiki/File:Dickturpin.jpgPublic DomainUnknown Artist, Public Domain, via Wikimedia Commons07/09/2026
02 Dick Turpin (1925).jpgWikimedia Commonshttps://commons.wikimedia.org/wiki/File:Dick_Turpin_(1925)_-_2.jpgPublic DomainFox Film Corporation, Public domain, via Wikimedia Commons07/09/2026
03 Black Horse.jpgFlickrhttps://flic.kr/p/dEtbXtCC BY 2.0“Black beauty” by Seniju, CC BY 2.007/09/2026
04 Adam Ant Brixton.jpgWikimedia Commonshttps://commons.wikimedia.org/wiki/File:AdamAntBrixt121220-41.jpgCC BY 2.0Raph_PH, CC BY 2.0, via Wikimedia Commons07/09/2026
05 William Powell Frith.jpgWikimedia Commonshttps://commons.wikimedia.org/wiki/File:William_Powell_Frith04a.jpgPublic DomainMaull & Polyblank, Public domain, via Wikimedia Commons07/09/2026
06 Highwayman and a Woman.jpgWikimedia Commonshttps://commons.wikimedia.org/wiki/File:Life_on_the_road_-_or,_Claude,_Turpin,_and_Jack,_being_a_complete_account_of_the_most_daring_adventures_of_the_notorious_highwaymen,_Claude_Duval,_Dick_Turpin,_and_Sixteen-string_Jack_(1800)_(14763476751).jpgPublic DomainInternet Archive Book Images, No restrictions, via Wikimedia Commons07/09/2026
07 A Highway Robbery.jpgWikimedia Commonshttps://commons.wikimedia.org/wiki/File:A_Highway_Robbery,_Fig_4.jpgPublic DomainAudrey Teago, Public domain, via Wikimedia Commons07/09/2026
08 A Highway Robbery.pngWikimedia Commonshttps://commons.wikimedia.org/wiki/File:Cham_-_Charivari_-_V3d119-c.pngPublic DomainAmédée de Noé, Public domain, via Wikimedia Commons07/09/2026
09 Dick Turpin Parish Register.jpgWikimedia Commonshttps://commons.wikimedia.org/wiki/File:Dick_turpin_parish_register.jpgPublic Domainunknown (18th century parish register), Public domain, via Wikimedia Commons07/09/2026
10 Dick Turpin’s Birthplace.jpgWikimedia Commonshttps://commons.wikimedia.org/wiki/File:Dick_Turpin%27s_Birthplace,_Hempstead,_Essex_-_geograph.org.uk_-_1820575.jpgCC BY-SA 2.0Dick Turpin’s Birthplace, Hempstead, Essex by Derek Voller, CC BY-SA 2.0, via Wikimedia Commons07/09/2026
11 Bluebell Inn.jpgWikimedia Commonshttps://commons.wikimedia.org/wiki/File:%27The_Bluebell_Inn%27,_Hempstead,_Essex_-_geograph.org.uk_-_148780.jpgCC BY-SA 2.0Robert Edwards / ‘The Bluebell Inn’, Hempstead, Essex /  CC BY-SA 2.0, via Wikimedia Commons07/09/2026
12 Quill and Ink.jpgFlickrhttps://flic.kr/p/6YEhtvCC BY 2.0“ink jar and quills” by Student of Rhythm, CC BY 2.007/09/2026
13 Thaxted.jpgWikimedia Commonshttps://commons.wikimedia.org/wiki/File:Thaxted_1744092_55a2e00f.jpgCC BY-SA 2.0Ben Brooksbank / Thaxted /  CC BY-SA 2.0, via Wikimedia Commons07/09/2026
14 Turpin’s Butchers’ Shop Thaxted.jpgWikimedia Commonshttps://commons.wikimedia.org/wiki/File:Shops,_Watling_Street,_Thaxted_-_geograph.org.uk_-_1363086.jpgCC BY-SA 2.0Humphrey Bolton / Shops, Watling Street, Thaxted /  CC BY-SA 2.0 via Wikimedia Commons07/09/2026
15 ‘Dick Turpin’s Cottage’ Thaxted.jpgWikimedia Commonshttps://commons.wikimedia.org/wiki/File:%27Dick_Turpin%27s_Cottage%27_Thaxted_Essex_England.jpgCC BY-SA 4.0Acabashi, CC BY-SA 4.0, via Wikimedia Commons07/09/2026
16 Deer.jpgWikimedia Commonshttps://commons.wikimedia.org/wiki/File:Deer_Family_Drawing.jpgPublic Domainno identifying information within book, Public domain, via Wikimedia Commons07/09/2026
17 King George II.jpgWikimedia Commonshttps://commons.wikimedia.org/wiki/File:King_George_II_by_Charles_Jervas.jpgPublic DomainStudio of Charles Jervas, Public domain, via Wikimedia Commons07/09/2026
18 Waltham Forest.jpgWikimedia Commonshttps://commons.wikimedia.org/wiki/File:London_Borough_of_Waltham_Forest_Sign_-_geograph.org.uk_-_3042138.jpgCC BY-SA 2.0London Borough of Waltham Forest Sign by David Anstiss, CC BY-SA 2.0, via Wikimedia Commons07/09/2026
19 Turpin Putting a Woman on the Fire.jpgWikimedia Commonshttps://commons.wikimedia.org/wiki/File:Turpin_Putting_a_Woman_on_the_Fire.JPGPublic DomainSee page for author, Public domain, via Wikimedia Commons07/09/2026
20 Raid.jpgWikimedia Commonshttps://commons.wikimedia.org/wiki/File:Life_on_the_road_-_or,_Claude,_Turpin,_and_Jack,_being_a_complete_account_of_the_most_daring_adventures_of_the_notorious_highwaymen,_Claude_Duval,_Dick_Turpin,_and_Sixteen-string_Jack_(1800)_(14580173887).jpgPublic DomainInternet Archive Book Images, Public Domain, via Wikimedia Commons07/09/2026
21 Duke of Newcastle.jpgWikimedia Commonshttps://commons.wikimedia.org/wiki/File:Thomas_Holles,_Duke_of_Newcastle_(BM_1902,1011.3354).jpgPublic DomainBritish Museum, Public domain, via Wikimedia Commons07/09/2026
22 Pub Sketch.jpgWikimedia Commonshttps://commons.wikimedia.org/wiki/File:Life_on_the_road_-_or,_Claude,_Turpin,_and_Jack,_being_a_complete_account_of_the_most_daring_adventures_of_the_notorious_highwaymen,_Claude_Duval,_Dick_Turpin,_and_Sixteen-string_Jack_(1800)_(14743633846).jpgPublic DomainInternet Archive Book Images, Public Domain, via Wikimedia Commons07/09/2026
23 Tyburn Tree.jpgWikimedia Commonshttps://commons.wikimedia.org/wiki/File:Tyburn_Tree_(4372859400).jpgCC BY 2.0Simon Harriyott from Uckfield, England, CC BY 2.0, via Wikimedia Commons07/09/2026
24 Chicken.jpgWikimedia Commonshttps://commons.wikimedia.org/wiki/File:Thai_Game_chicken_-_red_3.JPGvCC BY-SA 4.0PumpkinSky, CC BY-SA 4.0, via Wikimedia Commons07/09/2026
25 Whitestockings.jpgCanva AIN/AN/AGenerated by Eri Berry using Canva’s AI under Canva’s usage policies07/09/2026
26 Epping Forest, Loughton Camp.jpgWikimedia Commonshttps://commons.wikimedia.org/wiki/File:Epping_Forest,_Loughton_Camp_-_geograph.org.uk_-_548885.jpgCC BY-SA 2.0Nigel Cox / Epping Forest: Loughton Camp /  CC BY-SA 2.007/09/2026
27 Turpin’s Cave, Epping.jpgWikimedia Commonshttps://commons.wikimedia.org/wiki/File:Turpin%E2%80%99s_Cave,_Epping.jpgPublic DomainW.D. & H.O. Wills, Public domain, via Wikimedia Commons07/09/2026
28 Dick Turpin Murderer.gifWikimedia Commonshttps://commons.wikimedia.org/wiki/File:Dick_turpin_murderer.jpgPublic DomainThe Complete Newgate Calendar Volume III, Public domain, via Wikimedia Commons07/09/2026
29 Horses.jpgWikimedia Commonshttps://commons.wikimedia.org/wiki/File:%D0%A2%D1%80%D0%B8_%D0%BA%D0%BE%D0%BD%D1%96.jpgCC BY-SA 4.0Byrdyak, CC BY-SA 4.0, via Wikimedia Commons07/09/2026
30 Rooster.jpgFlickrhttps://flic.kr/p/cKypQyCC BY-SA 2.0“Rooster” by Andy Rogers, CC BY-SA 2.007/09/2026
31 Sheep.jpgFlickrhttps://flic.kr/p/JwzSaqCC BY 2.0“Sheep” by John Fowler, CC BY 2.007/09/2026
32 York Castle.pngFlickrhttps://flic.kr/p/2nxkWVDCC BY 2.0“Cliffords tower York” by The Hidden Hide with Ray, CC BY 2.007/09/2026
33 Saffron Walden.jpgFlickrhttps://flic.kr/p/2juiM2XPublic Domain“Postcard – Cross Keys Hotel, Saffron Walden, Essex” by Mark Crombie, Public Domain Mark07/09/2026
34 Trial Pamphlet.jpgWikimedia Commonshttps://commons.wikimedia.org/wiki/File:Trial_of_dick_turpin.jpgPublic DomainWard and Chandler, York, 1739, Public domain, via Wikimedia Commons07/09/2026
35 Gravestone of Dick Turpin.jpgWikimedia Commonshttps://commons.wikimedia.org/wiki/File:Gravestone_of_Dick_Turpin_York_Sep25.jpgCC BY-SA 4.0Malcolmxl5, CC BY-SA 4.0, via Wikimedia Commons07/09/2026
36 Daniel Defoe.jpgWikimedia Commonshttps://commons.wikimedia.org/wiki/File:Daniel_Defoe_Kneller_Style.jpgPublic DomainUnknownUnknown , style of Sir Godfrey Kneller, Public domain, via Wikimedia Commons07/09/2026
37 William Ainsworth.jpgWikimedia Commonshttps://commons.wikimedia.org/wiki/File:William_Harrison_Ainsworth_by_Daniel_Maclise.jpgPublic DomainDaniel Maclise, Public domain, via Wikimedia Commons07/09/2026
38 Rookwood Cover.pngWikimedia Commonshttps://commons.wikimedia.org/wiki/File:RookwoodCover.pngPublic DomainWilliam Harrison Ainsworth, Public domain, via Wikimedia Commons07/09/2026
39 Dick Turpin jumping Hornsey Tollgate.jpgWikimedia Commonshttps://commons.wikimedia.org/wiki/File:Dick_turpin_jumping_hornsey_tollgate.jpgPublic DomainGeorge Cruikshank; the book was written by William Harrison Ainsworth, Public domain, via Wikimedia Commons07/09/2026
40 The Ride to York.jpgWikimedia Commonshttps://commons.wikimedia.org/wiki/File:%E2%80%9CThe_Ride_to_York%E2%80%9D.jpgPublic DomainW.D. & H.O. Wills, Public domain, via Wikimedia Commons07/09/2026
41 Robin Hood shoots with Sir Guy.pngWikimedia Commonshttps://commons.wikimedia.org/wiki/File:Robin_shoots_with_sir_Guy_by_Louis_Rhead_1912.pngPublic DomainLouis Rhead, Public domain, via Wikimedia Commons07/09/2026
42 Penny Dreadful – Turpin.jpgWikimedia Commonshttps://commons.wikimedia.org/wiki/File:Penny_Dreadful_Turpin.jpgPublic DomainViles, Edward, Public domain, via Wikimedia Commons07/09/2026
43 Dick Turpin (1925) poster.jpgWikimedia Commonshttps://commons.wikimedia.org/wiki/File:Dick_Turpin_(1925)_poster.jpgPublic DomainFox Film Corporation, Public domain, via Wikimedia Commons07/09/2026
44 Dick Turpin and Tom King pottery figures.jpgWikimedia Commonshttps://commons.wikimedia.org/wiki/File:Dick_Turpin_and_Tom_King_pottery_figures_01.jpgCC014GTR, CC0, via Wikimedia Commons07/09/2026
45 Dick Turpin Information Board, George Street.jpgWikimedia Commonshttps://commons.wikimedia.org/wiki/File:Dick_Turpin_Information_Board,_George_Street_-_geograph.org.uk_-_7970734.jpgCC BY-SA 2.0Dick Turpin Information Board, George Street by David Hillas, CC BY-SA 2.0, via Wikimedia Commons07/09/2026
46 Eight Bells, Hatfield Plaque.jpgFlickrhttps://flic.kr/p/2rLvRWkCC BY 4.0“History of the Eight Bells” by Matt Brown, CC BY 4.007/09/2026
47 Bungay heritage plaque, Dick Turpin comes to Bungay.jpgWikimedia Commonshttps://commons.wikimedia.org/wiki/File:Bungay_heritage_plaque,_Dick_Turpin_comes_to_Bungay_-_geograph.org.uk_-_7553045.jpgCC BY-SA 2.0Bungay heritage plaque, Dick Turpin comes to Bungay by Adrian S Pye, CC BY-SA 2.0, via Wikimedia Commons07/09/2026

Intro images:

Image:Source Name:Source URL:Attribution:Licence Type:Date Downloaded:Modified?
Bridge End Gardens Saffron Walden.jpgFlickrhttps://flic.kr/p/dxR7Ki“Meeting up with Ola, Lisa, and Rex in Saffron Walden” by Tim Regan, CC BY 2.0CC BY 2.031/08/2026No
Chelmsford Cathedral.jpgFlickrhttps://flic.kr/p/7u9rHa“Chelmsford Cathedral” by fourthandfifteen, CC BY 2.0CC BY 2.031/08/2026No
Southend Pier With Greenery.jpgFlickrhttps://flic.kr/p/6Fe3eX“Southend Pier.” by Jim Linwood, CC BY 2.0CC BY 2.031/08/2026No
Colchester Castle.jpgFlickrhttps://flic.kr/p/DqxK3b“Colchester Castle” by William Marnoch, CC BY 2.0CC BY 2.031/08/2026No
Mersea Island Beach Huts.jpgFlickrhttps://flic.kr/p/2kYHhzg“Pretty pastel beach huts” by Jerry Clack, CC BY 2.0CC BY 2.031/08/2026No
Hobbs Cross Harlow.jpgFlickrhttps://flic.kr/p/2jtpvVB“Hobbs Cross, Harlow” by Sludge G, CC BY-SA 2.0CC BY-SA 2.031/08/2026No
Finchingfield.jpgFlickrhttps://flic.kr/p/7TWVL6“Finchingfield” by Brian Snelson, CC BY 2.0CC BY 2.031/08/2026No
Harlow Riverboats Sunset.jpgFlickrhttps://flic.kr/p/2f1Tuvv“Harlow” by Kent Wang, CC BY-SA 2.0CC BY-SA 2.031/08/2026No
St Peter on the Wall.jpgFlickrhttps://flic.kr/p/2pbUhCC“Chapel of St Peter on the Wall” by Tom Bastin, CC BY 2.0CC BY 2.031/08/2026No
Swans River Stour.jpgFlickrhttps://flic.kr/p/2jwdsfA“River Stour” by Jason Boldero, CC BY 2.0CC BY 2.031/08/2026No
Thaxted Guildhall and Church.jpgFlickrhttps://flic.kr/p/4qhScp“Thaxted guildhall” by Marco Chiesa, CC BY 2.0CC BY 2.031/08/2026No
Hedingham Castle.jpgFlickrhttps://flic.kr/p/2m7mEwe“Hedingham Castle – Norman Keep in England” by Steve Knight, CC BY 2.0CC BY 2.005/09/2026No
Hatfield Forest Lake.jpgFlickrhttps://flic.kr/p/2cXBELC“Hatfield Forest Lake” by Jason Boldero, CC BY 2.0CC BY 2.031/08/2026No

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