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Here is an open-ended challenge.

Find the longest series of English words such that the final four letters of word $n$ are the same as the first four letters of word $n+1$.

Example

(3 words) quintuplet plethora horary

At that point I stopped because I could find no dictionary words beginning with 'rary'.

Rules

  1. Only words that are defined in dictionary.com are allowed. Plurals and verb conjugation are allowed. If a word is doubtful then the community will decide by their votes.

  2. No repeats. No word must appear more than once in a list.

  3. Four letter words are allowed. But if you use one then it must be the last in the list.

  4. Before posting, check the longest answer so far. If you cannot do better then please don't post. This prevents many equal answers.

  5. If by chance two or more people post equal solutions at the same time then the one that is earliest on the SE system clock is counted and the others are not. As a courtesy, please delete your answer if you were beaten time-wise. If it is a dead-heat by the system clock then the answers will be considered equal.

5a. If by examining someone else's answer you are able to improve it by inserting one or more words then this is allowed and you may give it as a separate answer. Note that the consensus from reading other peoples' comments is that this is disapproved of. If you do it you may get down-voted unless you can justify it to the community.

  1. Please give your answer in the following format so that others can easily see what they have to beat.

Answer format

(3 words) quintuplet plethora horary

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    $\begingroup$ I am staunchly against rule 5a. Because right now @randal'thor is working on his list and has reached 49 words (at the time of this comment). Maybe he will reach 100 and then stop. And then someone comes along tomorrow and adds his own answer by inserting one word somewhere between rand's list, and that's a valid strategy? Hardly seems fair. $\endgroup$
    – CodeNewbie
    Aug 26 '15 at 12:44
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    $\begingroup$ I really don't wanna be "that guy", but this is one of those questions, that are too easily solved by a machine. The dumbest brute-forcing approach yielded a chain of length 885 pretty fast. $\endgroup$
    – dmg
    Aug 26 '15 at 13:26
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    $\begingroup$ So post your 885 word list and we can check it. $\endgroup$
    – Kingrames
    Aug 26 '15 at 14:10
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    $\begingroup$ Seems to me it would be a better puzzle if there were a restriction disallowing the use of the same four-letter link more than once. So that a sequence like this would be forbidden: makeover overturn turnover overcome $\endgroup$
    – dennisdeems
    Aug 26 '15 at 16:52
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    $\begingroup$ I’m voting to close this question because open-ended puzzles are off-topic as of May 2019 (and since this is explicitly no-computers, brute-force "optimization" isn't allowed) $\endgroup$
    – bobble
    Jul 12 '21 at 4:07
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(This answer previously had a solution probably found by computer search)

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    $\begingroup$ I did use a computer to verify that all of the words are on Dictionary.com. $\endgroup$
    – 2012rcampion
    Aug 27 '15 at 20:14
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    $\begingroup$ If you came up with this list without using a computer, I don't know whether to give you a medal or tell you to get a life! :-) $\endgroup$
    – Rand al'Thor
    Aug 27 '15 at 20:20
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    $\begingroup$ @randal'thor I have too much schoolwork to do this completely by hand; no medal for me I'm afraid =P $\endgroup$
    – 2012rcampion
    Aug 27 '15 at 20:21
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(4 words) monopoly polymath mathematically allying

(8 words) sleepover overwork workshop shoplift liftoffs offside sideburn burnout

(123 words) thigh highjack jackboot, bootstrap trapdoor doorstep stepbrother therein, reinterpret preterm termini minidrama ramada, madam adamant mantram tramp rampart, partake takeover overflow flowering ringside, sidestep stepmother there heretofore forevermore, moreover overfree freeform formant mantrap, trapdoor doorbell bellpull pullover overturn, turnover overwork workshop shoplift liftoffs, offspring ringtone toneless lessens sensitising, singsong songbird birdsong songbook bookkeepers, persistent tenterhook hooking kinglike likelihood, hoodwink winking kingship shipload loadmaster, stereotype typewriter iterant ranting tingling, lingering ringworm wormwood woodworm wormhole, holeless lessons sonship shipwreck reckoner, onerous rousing singalong longhorn hornbeam, beamish mishmash mashing hinge ingest, gesticulate latewood woodcock cockpits pitstop, stopping pinging gingerbread readership shipyard, yardland landlord lordship shipment mentoring, ringneck necklace lacewing wingspan spanking, kingfisher sherlock lockdown downside sidelong, longboat boatfuls fulsome somewhere herein, reinforcement menthol tholepins pinstripe riper

(commas every 5 words, to make the count easier)

Thanks to all those who helped me with this, including Kingrames, Anachor, Gordon K, Code Newbie, Rj Geraci, and others.

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  • $\begingroup$ change long to longing and then ginger or something else dunno. Or longest and gesture... dunno. Cool stuff. $\endgroup$
    – Going hamateur
    Aug 26 '15 at 17:38
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    $\begingroup$ Man you nuked our comments from orbit! I suppose I'll just be one of "the others" then, LOST-style. ;) $\endgroup$
    – Kingrames
    Aug 26 '15 at 20:38
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    $\begingroup$ You can extend any of the gaps between "...over" and "over...." with the following (and any others like them): overhand handover overpass passover overhang hangover overhung hungover overslip slipover overtake takeover overturn turnover overstep stepover $\endgroup$
    – NeedAName
    Aug 27 '15 at 1:31
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    $\begingroup$ Add to the above string: overhear heart earthmover $\endgroup$
    – NeedAName
    Aug 27 '15 at 1:45
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    $\begingroup$ @NeedAName That's Evil. $\endgroup$
    – Rohcana
    Aug 27 '15 at 6:45
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From exchange to stack overflow:

(45 words) exchange -> angelfish -> fishbone -> bonemeal -> mealtime -> timeline -> lineament -> mentalist -> listless -> lessons -> sonship -> shipside -> sidewalk -> walkyries -> riesling -> linguistic -> stickball -> ballgame -> gameplay -> playmate -> mateship -> shipyard -> yardland -> landlord -> lording -> dinging -> gingerbread -> readjust -> justifies -> fiesta -> establisher -> sherlock -> lockstep -> stepfather -> therefore -> forest -> restack -> tacking -> kingfish -> fishtail -> tailrace -> racemism -> mismove -> mover -> overflow

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    $\begingroup$ Nice one (and welcome to Puzzling.SE!) I've managed to beat it with 39 though :-) $\endgroup$
    – Rand al'Thor
    Aug 26 '15 at 12:12
  • $\begingroup$ Thanks ;-) Unfortunatelly my lunch break was over, so I had to stop. Maybe I'll continue tonight. $\endgroup$
    – Christoph
    Aug 26 '15 at 12:15
  • $\begingroup$ In the last word you used 5 letters from the previous word. You ended up at tack, not stack. $\endgroup$
    – CodeNewbie
    Aug 26 '15 at 12:36
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    $\begingroup$ Is that an overflow ? :o) $\endgroup$
    – The random guy
    Aug 26 '15 at 12:48
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    $\begingroup$ @CodeNewbie, you are right, I fixed it. All the way to overflow $\endgroup$
    – Christoph
    Aug 26 '15 at 13:11
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I think I have finally locked myself in at 174 words:

thigh, highjack, jackboot, bootstrap, trapdoor, doorstep, stepbrother, therein, reinterpret, preterm, termini, minidrama, ramada, madam, adamant, manta, antacid, acidifies, fiesta, establishment, mentalist, listen, stench, enchantment, menthols, holster, stereotype, typecast, castaways, wayside, sidearm, earmark, markdown, downcast, caste, aster, stertorous, rousing, singletons, tonsure, surefire, firearm, earmarking, kingpins, pinstripe, ripest, pestering, ringlike, likelihood, hoodwink, winking, kingship, shipload, loadstar, starch, archbishop, shopkeepers, persecute, cutest, testament, mentoring, ringside,sidecars, carsick, sickbeds, bedside, sidekick, kickback, backbone, bonehead, headband, bandanna, annalist, listens, tense, ensembles, blessing, singletree, treed, reedit, editorship, shipmate, materialising, singsong, songbird, birdbath, bathe, atheistic, stickleback, backdate, dateline, lineage, eagerest, restaff, taffrail, railroad, roadbeds, bedsore, sorehead, headgear, gearing, ringworm, wormwood, woodblock, lockouts, outscore, corespondent, dentistry, strychnine, ninepin, epinephrins, rinse, inseam, seamanship, shippers, perseverance, ancestor, storage, rageless, lessees, seesawing, wingspan, spanking, kingfishers, herself, selfish, fishbowl, bowlfuls, fulsome, somebody, bodysuit, suitcase, casein, seiner, inerrant, ranting, tinge, ingest, gestapos, apostleship, shipwreck, reckless, lessens, sensationalist, listener, enervating, tinging, gingerbread, readdressing, singe, ingesting, tingling, lingering, ringing, gingersnap, snapdragon, agonizing, zinging, ginghams, hamster, sterling, linguistic, stick, ticking, kingfisher, sheriff, riffing, fingering, ringmaster, sternest, nestling, linguines, inescapable, abled, bled

Thanks to rand al'thor, Ian MacDonald, and Anachor for the help!

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  • $\begingroup$ Sorry, "correspondent" is mis-spelled and this invalidates the link. $\endgroup$
    – Rand al'Thor
    Aug 26 '15 at 16:05
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    $\begingroup$ Actually it isn't. dictionary.reference.com/browse/corespondent?s=t Though I have to confess, I wasn't expecting that to be a real word! $\endgroup$
    – Kingrames
    Aug 26 '15 at 16:19
  • $\begingroup$ OK, my mistake! +1 then, although I've just beaten you with 104 :-) $\endgroup$
    – Rand al'Thor
    Aug 26 '15 at 16:21
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    $\begingroup$ Take off the first couple words and put in dictionary.reference.com/browse/overboot instead? $\endgroup$
    – f''
    Aug 27 '15 at 2:12
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    $\begingroup$ You could replace "thigh" with "overtake, takeover, overhang, hangover, overhigh" which leads into highjack. You could say that was ... overdone? over the top? game over? okay I'll stop... $\endgroup$
    – corsiKa
    Aug 27 '15 at 4:09
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350 and counting :)

highball balladeer deerflys flyspeck pecking kingfish fishable ables bless lessees seesawing wingback backache aches chestfuls fulsome somebody bodybuilding dinging gingerbread readapting tinge ingest gestapos apostasies siesta establisher sherbert berthing hinge ingestant tantalic alice licence enceinte integrate raters tersest sestet stethoscope copenhagen agency encyclic cliches chestier tiering ringbolt bolthead headaches chestnuts nutshell hellbent benthal thalami lamia amias miasmas smash masher sherd herdswomen omens menschen chenille illegal egalite liter iterant ranting tinging gingering ringdove dover overabundance ancestor storables blessedest destain tainting tingling lingering ringing gingersnap snapback backbencher cherish rishis shist histamin amino minoring ringlike likelihood hoodless lessens sensate sateen teener energizing zinging ginghams hamster stereochemistry strychnine ninefold foldboat boatbill billeter eterne ernest nester stereoscope coper opera peradventure tureen reenactment mentalist listen stench enchainment menthol thole holeless lessons sonships hipshot shotguns gunship shipload loadstar starch archaistic stick ticking kingfisher sheriff riffing fingering ringmaster stereoscopy copybook bookcase casebook bookend kendo endomorph orphan phantast taste aster stereotape tapeline lineage eagerest restack tackifies fiesta establishment menthols holster stereotype typebars barstool toolhead headachier hierarch archbishop shope hoper operandi andiron ironbark barkeep keepers persecute cutest testament mentioner onerous rousing singletons tonsorial rialto altogether therapist pistil stilbestrol troll rollback backbenchers herself selfheal healer alertest testee steeling linguistic sticking kingpins pinscher cherisher sherlock locking kingship shipmaster stereotypers persevering ringneck neckband bandanna annalist listens tense ensembles blessing singletree treed reedit edith dither there hereabout boutiques quester sternest nestlike likest kestrel trellising singsong songbird birdbath bathe atheistic stickleback backbone boneblack lackeyed eyedroppers persimmons monseigneur neurogram grammars marseille illegitimate materialist lister stertorous roustabout bouts outscore corelate lateen teenyboppers persist sisterhood hoodwink winking kingside sidearm earmark markdown downcast castaways wayside sideband bandoleer leering ringside sideburn burnouts outscoring ringtail tailbone bonefish fishbone bonehead headband bandwagon agonise niseis seismicity cityward wardens dense enserfing fingernail nailhead headgear gearcase caseload loadstone tones oneself selfhood hoodwinking kingwood woodblock lockouts outsell sellout louts outsets setscrew crewelwork workboat boatswain wainscot scotland landfall fallback backdate dateline linear nearest restaff taffrail railbird birdbrain rainbows bowshot shots hotshots hotspur spurge urgency encyclopedic edict dictaphone honest nestor store toreador adoring ringtoss tosspot spots potshard hardback backdoor doorbell belletristic stickouts outshone honeycomb combatant tantalum alumina minacity citywide widely...

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    $\begingroup$ Pretty good answer, but the question states "no computers". (I do think that that's an unreasonable restriction though.) $\endgroup$
    – Deusovi ♦
    Aug 27 '15 at 9:46
  • $\begingroup$ Oops ! You are right I cheated! I had fun to buid up this little program, though. I'm sorry, please all feel free to get inspired by this answer =) $\endgroup$
    – Bitoubi
    Aug 27 '15 at 10:00
  • $\begingroup$ You don't need to apologize! Hope to see you around on Puzzling.SE more often! $\endgroup$
    – Deusovi ♦
    Aug 27 '15 at 10:09
  • $\begingroup$ @Deusovi what if I don't use a computer, but I use an answer of someone that did? (But then again, how did I post an answer if I didn't use a computer?) $\endgroup$
    – John Dvorak
    Sep 22 '17 at 17:38
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A very similar puzzle to this was posted on PPCG, and I answered it, but it's significantly harder with an overlap of four letters instead of three. I modified my code from that problem (after digging through old files to find it and fixing some bugs), and, after a few minutes, I got this chain of length 300:

Aachen -> chenille -> illegitimate -> materialistic -> stick -> tick -> tickling -> linguistic -> stickpins -> pins -> pinstripe -> ripens -> pens -> pensioner -> onerous -> rousing -> singletons -> tonsuring -> ringside -> sidetrack -> racketeering -> ring -> ringmaster -> sterling -> lingering -> ringing -> gingerbread -> readjust -> justifies -> fiestas -> stashed -> shed -> shedding -> dinging -> gingersnap -> snap -> snappers -> persecute -> cutest -> test -> tester -> sternest -> nesting -> tinge -> ingest -> gesticulate -> late -> latent -> tenth -> enthronement -> mentoring -> ringworm -> wormwood -> wood -> woodwork -> workmanlike -> like -> likewise -> wisecracking -> kingship -> shippers -> persist -> sisterhood -> hoodwinking -> kingfishers -> herself -> selfish -> fisher -> sheriff -> riffraff -> raffish -> fish -> fishtail -> tailgate -> gate -> gatepost -> poster -> stereotype -> typeface -> facet -> acetaminophen -> phenomenons -> nonsupport -> portables -> blessing -> sing -> singsong -> songbird -> birdwatcher -> cheroot -> root -> rootless -> lessens -> sensationalist -> listens -> tense -> ensembles -> bless -> less -> lessees -> seesawing -> wing -> wingspread -> readership -> shipload -> load -> loadstar -> star -> starch -> archdeacons -> consign -> sign -> signpost -> postmark -> markdown -> down -> downwind -> windmill -> millipede -> pedestal -> stalwart -> wartime -> timekeepers -> perseverance -> ancestry -> strychnine -> nineteenth -> enthusiastic -> stickleback -> backfire -> firetrap -> trapdoor -> doorways -> ways -> wayside -> sideshows -> hows -> howsoever -> ever -> everybody -> body -> bodywork -> workbook -> bookkeepers -> persimmons -> monstrous -> roustabout -> bout -> bouts -> outs -> outstrip -> trip -> tripled -> pled -> pledge -> edgewise -> wise -> wiseacres -> crescent -> cent -> centigram -> gramophone -> honeymoon -> moonstruck -> rucksack -> sackfuls -> fulsome -> somewhere -> heretofore -> forestall -> tall -> tallyhoed -> hoedown -> downcast -> cast -> castor -> storybook -> book -> bookcase -> casework -> work -> workshop -> shoplift -> liftoffs -> offs -> offside -> sidewalk -> walkouts -> outspread -> read -> readouts -> outside -> sideline -> linemen -> emend -> mend -> mendicant -> cant -> cantilever -> evermore -> moreover -> overkill -> killdeer -> deerskin -> skin -> skinhead -> headword -> word -> wordplay -> play -> playback -> backstairs -> airsick -> sickbeds -> beds -> bedsore -> sore -> sorehead -> head -> headline -> line -> linefeed -> feed -> feedback -> backside -> sideshow -> showdown -> downhill -> hillock -> lockstep -> stepbrother -> therein -> rein -> reinterpret -> pretend -> tend -> tenderfoot -> foot -> footstep -> stepmother -> therapist -> pistons -> tons -> tonsure -> sure -> surefire -> fireside -> sidekick -> kickback -> backhand -> hand -> handpick -> pickaback -> back -> backstops -> topsoil -> soil -> soils -> oils -> oilskin -> skins -> kinswomen -> omens -> menswear -> wearisome -> somewhat -> what -> whatever -> everywhere -> here -> herewith -> with -> withhold -> hold -> holdover -> overland -> landlady -> ladybird -> bird -> birdbath -> bathes -> thespian -> pianissimi -> simile -> milepost -> posture -> tureen -> reenlist -> listen -> stenches -> chestnuts -> nuts -> nutshell -> hell -> hellion -> lion -> lionizing -> zing -> zinging -> gingersnaps -> naps

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  • $\begingroup$ You have a lot of 4 letter words. tick, pins pens, ring, shed, snap, test... These are invalid as per rule 3. Only the last word snap is a valid four letter word, given the rules. $\endgroup$
    – CodeNewbie
    Aug 27 '15 at 4:31
  • $\begingroup$ @CodeNewbie I didn't notice that rule. I have modified my program and am generating a valid sequence now. $\endgroup$
    – KSFT
    Aug 27 '15 at 5:13
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    $\begingroup$ @KSFT note the no computers tag $\endgroup$
    – Rohcana
    Aug 27 '15 at 7:36
  • $\begingroup$ @KSFT: And you still have 4-letter word inside (cent, cast, sign, offs, back, sure, and many others) $\endgroup$
    – justhalf
    Aug 27 '15 at 10:49
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    $\begingroup$ Actually you can just remove those 4-letter words, since they can be removed while keeping the chain valid. $\endgroup$
    – justhalf
    Aug 28 '15 at 5:08
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(4 words) building ding dinge inge

(13 word) backdoor doorpost postface facedown downspouts outsprang rangeland landmass masacres crescendo endocardial Dialogues Guesswork workmate material rialto altocumulus ulus

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  • $\begingroup$ hope the answer is in a correct way :) $\endgroup$
    – Megasa3
    Aug 26 '15 at 11:12
  • $\begingroup$ @randal'thor so you mean that a 4 letter word cant be in the middle? Then there can be only maximum one word and it has to be at end? $\endgroup$
    – Megasa3
    Aug 26 '15 at 11:18
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    $\begingroup$ I'm not sure. The OP says words can't be repeated, therefore 4-letter words can only be at the end; but that logic seems to be wrong. $\endgroup$
    – Rand al'Thor
    Aug 26 '15 at 11:18
  • $\begingroup$ I too believe OP is incorrect in his logic. The example of "building ding dinge" seems completely appropriate. I'd frown on something like "takeover over overtake take taken", I don't think that's in the spirit of it. But with ding being so different from the other words, that seems completely legit. $\endgroup$
    – corsiKa
    Aug 27 '15 at 4:13
  • $\begingroup$ I agree with the OP. There is no need for the intermediary "ding" to link bulding and dinge, and in a puzzle what is unnecessary is de trop. $\endgroup$
    – dennisdeems
    Aug 27 '15 at 14:50

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