Thestoryissetcirca1790intheDutchsettlementofTarryTown,inasecludedglencalledSleepyHollow.IttellsthestoryofIchabodCrane,asycophantic,lean,lanky,andextremelysuperstitiousschoolmasterfromConnecticut,whocompeteswithAbraham"BromBones"VanBrunt,thetownrowdy,forthehandof18-year-oldKatrinaVanTassel,thedaughterandsolechildofawealthyfarmer,BaltusVanTassel.AsCraneleavesapartyheattendedattheVanTasselhomeonanautumnnight,heispursuedbytheHeadlessHorseman,whoissupposedlytheghostofaHessiantrooperwhohadhisheadshotoffbyastraycannonballduring"somenamelessbattle"oftheAmericanRevolutionaryWar,andwho"ridesforthtothesceneofbattleinnightlyquestofhishead".Ichabodmysteriouslydisappearsfromtown,leavingKatrinatomarryBromBones,whowas"tolookexceedinglyknowingwheneverthestoryofIchabodwasrelated".AlthoughthenatureoftheHeadlessHorsemanisleftopentointerpretation,thestoryimpliesthattheHorsemanwasreallyBromBonesindisguise.
TheLegendofSleepyHollowwasbasedonaGermanfolktale,setintheDutchcultureofPost-RevolutionaryWarinNewYorkState.TheoriginalfolktalewasrecordedbyKarlMusäus.AnexcerptofMusäus:
Theheadlesshorsemanwasoftenseenhere.AnoldmanwhodidnotbelieveinghoststoldofmeetingtheheadlesshorsemancomingfromhistripintotheHollow.Thehorsemanmadehimclimbupbehind.Theyrodeoverbushes,hills,andswamps.Whentheyreachedthebridge,thehorsemansuddenlyturnedintoaskeleton.Hethrewtheoldmanintothebrookandsprangawayoverthetreetopswithaclapofthunder.[1]
ThedénouementofthefictionaltaleissetatthebridgeoverthePocanticoRiverintheareaoftheOldDutchChurchandBuryingGroundinSleepyHollow.ThecharactersofIchabodCraneandKatrinaVanTasselmayhavebeenbasedonlocalresidentsknowntotheauthor.ThecharacterofKatrinaisthoughttohavebeenbaseduponEleanorVanTasselBrush,inwhichcasehernameisderivedfromthatofEleanor'sauntCatrienaEckerVanTessel.
Irving,whilehewasanaide-de-camptoNewYorkGov.DanielD.Tompkins,metanarmycaptainnamedIchabodCraneinSacketsHarbor,NewYorkduringaninspectiontouroffortificationsin1814.Hemayhaveborrowedthenamefromthecaptainandpatternedthecharacterin"TheLegend"afterJesseMerwin,whotaughtatthelocalschoolhouseinKinderhook,furthernorthalongtheHudsonRiver,whereIrvingspentseveralmonthsin1809.[2]
"TheLegendofSleepyHollow"followsatraditionoffolktalesandpoemsinvolvingasupernaturalwildchase,includingRobertBurns'sTamO'Shanter(1790),andBürger'sDerwildeJäger,translatedasTheWildHuntsman(1796).