{"id":3962,"date":"2026-08-14T20:00:06","date_gmt":"2026-08-15T00:00:06","guid":{"rendered":"https:\/\/storiesofappalachia.com\/?p=3962"},"modified":"2026-08-12T09:52:27","modified_gmt":"2026-08-12T13:52:27","slug":"old-dill-asher-the-kentucky-pioneer-who-became-a-legend","status":"publish","type":"post","link":"https:\/\/storiesofappalachia.com\/?p=3962","title":{"rendered":"Old Dill Asher: The Kentucky Pioneer Who Became a Legend"},"content":{"rendered":"<p><span class=\"embed-youtube\" style=\"text-align:center; display: block;\"><iframe loading=\"lazy\" class=\"youtube-player\" width=\"640\" height=\"360\" src=\"https:\/\/www.youtube.com\/embed\/jsqtim0LSts?version=3&#038;rel=1&#038;showsearch=0&#038;showinfo=1&#038;iv_load_policy=1&#038;fs=1&#038;hl=en-US&#038;autohide=2&#038;wmode=transparent\" allowfullscreen=\"true\" style=\"border:0;\" sandbox=\"allow-scripts allow-same-origin allow-popups allow-presentation allow-popups-to-escape-sandbox\"><\/iframe><\/span><\/p>\n<p>Dillion \u201cOld Dill\u201d Asher was one of the early pioneers of southeastern Kentucky, a frontier soldier and farmer who became the toll keeper at the Cumberland River ford at what\u2019s now Pineville, giving him a front row seat to the early settlement of the state.<\/p>\n<p>In this episode, we tell Old Dill\u2019s story, from his connection to the first settlers in what became Tennessee, his military service, his journeys into Kentucky along the Wilderness Road, the settlement of Red Bird Valley, and his, shall we say, \u201ccomplicated family life.\u201d<\/p>\n<p>Along the way, we try to separate what can be documented from the rich folklore that grew up around one of eastern Kentucky&#8217;s most colorful pioneers.\u00a0<\/p>\n<p>If you enjoy stories like this, please subscribe to the Stories podcast so you don\u2019t miss any of them.<\/p>\n<p>Thanks for listening!<\/p>\n<div class=\"powerpress_player\" id=\"powerpress_player_5781\"><audio class=\"wp-audio-shortcode\" id=\"audio-3962-1\" preload=\"none\" style=\"width: 100%;\" controls=\"controls\"><source type=\"audio\/mpeg\" src=\"https:\/\/dts.podtrac.com\/redirect.mp3\/api.spreaker.com\/v2\/episodes\/73847601\/download.mp3?_=1\" \/><a href=\"https:\/\/dts.podtrac.com\/redirect.mp3\/api.spreaker.com\/v2\/episodes\/73847601\/download.mp3\">https:\/\/dts.podtrac.com\/redirect.mp3\/api.spreaker.com\/v2\/episodes\/73847601\/download.mp3<\/a><\/audio><\/div><p class=\"powerpress_links powerpress_links_mp3\" style=\"margin-bottom: 1px !important;\">Podcast: <a href=\"https:\/\/dts.podtrac.com\/redirect.mp3\/api.spreaker.com\/v2\/episodes\/73847601\/download.mp3\" class=\"powerpress_link_pinw\" target=\"_blank\" title=\"Play in new window\" onclick=\"return powerpress_pinw('https:\/\/storiesofappalachia.com\/?powerpress_pinw=3962-podcast');\" rel=\"nofollow\">Play in new window<\/a> | <a href=\"https:\/\/dts.podtrac.com\/redirect.mp3\/api.spreaker.com\/v2\/episodes\/73847601\/download.mp3\" class=\"powerpress_link_d\" title=\"Download\" rel=\"nofollow\" download=\"download.mp3\">Download<\/a><\/p><p class=\"powerpress_links powerpress_subscribe_links\">Subscribe: <a href=\"https:\/\/storiesofappalachia.com\/?feed=podcast\" class=\"powerpress_link_subscribe powerpress_link_subscribe_rss\" target=\"_blank\" title=\"Subscribe via RSS\" rel=\"nofollow\">RSS<\/a><\/p><!--powerpress_player-->","protected":false},"excerpt":{"rendered":"<p>Dillion \u201cOld Dill\u201d Asher was one of the early pioneers of southeastern Kentucky, a frontier soldier and farmer who became the toll keeper at the Cumberland River ford at what\u2019s now Pineville, giving him a front row seat to the early settlement of the state. In this episode, we tell Old Dill\u2019s story, from his [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_jetpack_newsletter_access":"","_jetpack_dont_email_post_to_subs":false,"_jetpack_newsletter_tier_id":0,"_jetpack_memberships_contains_paywalled_content":false,"_jetpack_feature_clip_id":0,"_jetpack_memberships_contains_paid_content":false,"footnotes":"","jetpack_publicize_message":"","jetpack_publicize_feature_enabled":true,"jetpack_social_post_already_shared":true,"jetpack_social_options":{"image_generator_settings":{"template":"highway","default_image_id":0,"font":"","enabled":false},"version":2},"jetpack_post_was_ever_published":false},"categories":[9,13],"tags":[479,104,1047,1908,1904,88,1898,1905,1901,1274,1907,89,796,1900,1906,1899,501,1902,1903,90],"class_list":["post-3962","post","type-post","status-publish","format-standard","hentry","category-personalities","category-the-appalachian-frontier","tag-appalachian-folklore","tag-appalachian-history","tag-appalachian-pioneers","tag-chief-red-bird","tag-clay-county-kentucky","tag-daniel-boone","tag-dillion-asher","tag-early-kentucky","tag-eastern-kentucky-history","tag-frontier-history","tag-kentucky-folklore","tag-kentucky-frontier","tag-kentucky-history","tag-kentucky-pioneer","tag-kentucky-settlers","tag-old-dill-asher","tag-pioneer-life","tag-red-bird-kentucky","tag-red-bird-valley","tag-wilderness-road"],"jetpack_publicize_connections":[],"jetpack_sharing_enabled":true,"jetpack_shortlink":"https:\/\/wp.me\/p6TX4A-11U","jetpack_featured_media_url":"","_links":{"self":[{"href":"https:\/\/storiesofappalachia.com\/index.php?rest_route=\/wp\/v2\/posts\/3962","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/storiesofappalachia.com\/index.php?rest_route=\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/storiesofappalachia.com\/index.php?rest_route=\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/storiesofappalachia.com\/index.php?rest_route=\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/storiesofappalachia.com\/index.php?rest_route=%2Fwp%2Fv2%2Fcomments&post=3962"}],"version-history":[{"count":3,"href":"https:\/\/storiesofappalachia.com\/index.php?rest_route=\/wp\/v2\/posts\/3962\/revisions"}],"predecessor-version":[{"id":3965,"href":"https:\/\/storiesofappalachia.com\/index.php?rest_route=\/wp\/v2\/posts\/3962\/revisions\/3965"}],"wp:attachment":[{"href":"https:\/\/storiesofappalachia.com\/index.php?rest_route=%2Fwp%2Fv2%2Fmedia&parent=3962"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/storiesofappalachia.com\/index.php?rest_route=%2Fwp%2Fv2%2Fcategories&post=3962"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/storiesofappalachia.com\/index.php?rest_route=%2Fwp%2Fv2%2Ftags&post=3962"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}