Have you ever wondered how the name Pentland (and now Penland) came to be?  Some have written that the name Pentland is another name for Pictland, and pre-dates the Clans.  Following is an account of how the Pentland Firth got it's name about a thousand years ago:
    { P E N T L A N D }
  The derivation of the term "Pentland" is uncertain.   Blaeu, in his Geographical Atlas, gives the following tradition respecting the origin of the name.  The Picts, on being defeated by the Scots, fled to Duncans-Bay, whence they crossed over to Orkney, but meeting with opposition from the natives, they were forced to retire; and on their way back to Caithness, they all perished in the Firth, from which catastrophe it was ever after the Pictland or Pentland Firth.     Buchanan calls it "Fretum Penthlandicum" from one Penthus;  but who this Penthus was, he does not say.  It owes it's name most probably to some circumstance connected with the Picts.
{Quoted from "The Civil and Traditional History of Caithness from the 10th Century", by James T. Calder}

Our search is for:  Where did the name Pentland originate?  --  Who were
the first family members?  --  Where did they live?  --  Who was the Pentland immigrant  that first came to America duing the 1600s?  --   Was that person the ancestor of William, Robert, George and Alexander?  --  If not, who was their ancestor, or ancestors?  Who were connecting family members from that early ancestor to these four?

There is a story (unproven) about how the first Pentland family came about.   It starts with Galam Cennalath, the ancient "King of the Picts"
who died in 580 A.D.   The story goes that his descendants inter-married with the children of the Norse Jarls, (who had invaded from the north), for
at least five centuries.    Galam's son was Madach who became the "1st Earl of Atholl."  Madach married Margaret of Orkney and they had a son named Harold Maddadson.  {It should be noted that in those days in the Pict society, the children took the mother's name}   Harold married Gormlath MacHeth, who was also born in Scotland.  (Gormlath was also known as Hvarflod MacHeth)  They had two sons, David and John Haraldssen.   About  500 years later another David  gained the title of "Jarl David of Orkney" and also succeeded to the title of "Earl of Caithness" in 1205 A.D.    A mere five years later Jarl David asked his brother-in-law, Thorkel Petlandi to take his son William out of harm's way, for he feared for his life if he stayed in Orkney or Caithness.   Thorkel gathered some family members and moved to Edislaw in Perthshire near to their relatives, the Duffs and the Murry's.   There, William grew to be an adult, and he married Margeret Murry.   William and Margeret had three sons,  Jarl David died in 1214.   His brother John gained the title of "Jarl of Orkney and he also succeeded to the title of "Earl of Caithness."   His territory was confiscated by  King Alexander, II of Scotland for his unlawful killing of the Bishop of Caithness, although he was restored on John's payment of a huge fine.   John died in 1231, without a son.   He was murdered by his servants in revenge for his supposed implication in the murder of the Bishop of Caithness.  

Another Version:
The Viking Jarl that had been sent to Orkney with orders to kill all the Pictish population living there, instead lived peacefully with them.   He heard that an army was being dispatched from Norway to do the job he
had failed to do.   Because he was fearful for the safety of his family, he arranged for his three daughters to be married to three of the sons of the Pict leader(whose name was latinised to be Owen Pictlandii.    The three couples were put into a boat with sufficient wealth to enable them to establish themselves, and sent to the Scottish mainland. (This story was related to us by a Pentland relative who was researching his roots in Ireland)  
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     While researching the early history of Scotland, Patrick Penland has discovered that there really was a Pentland Clan.  The picture to the left shows the "Clan Badge" of that time. (notice the simularities to the "Pentland Coat of Arms")   Now, the Clan is only listed as an 'armigerous clan'.   An armigerous clan is a Scottish clan, family or name which is registered with the Court of Lord Lyon and once had a chief who bore the original coat of arms, but does not have a chief currently recognized as such by Lyon Court.  Before 1745 all chiefs had arms;  however, not all of these are recorded in the Public Register of All Arms and Bearings in Scotland, which was only established in 1672.
     In Scottish heraldry the original coat of arms was only held by chiefs or heads of clans, families or names.  A clan is considered a "noble incorporation" because
a clan chief is a title of honour in Scotland and the chief confers his or her noble status onto the clan.  Because armigerous clans do not have such chiefs, they are not recognized as noble communities and have no legal standing under Scots law.  Scottish clans have been around a long time (even before Christianity came to Scotland around 500 A.D.).  It may be reasonable to assume that the Pentland Clan held land in the Northern Highlands, when Robert the Bruce took it,  and gave it over to the Sinclair family in 1316.

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      An Early Pentland Badge
The Following both Refer to the Pentland Hills and the "Battle of Rullion Green in 1666
Battle-Song of the Pentlands
The Battle of the Pentlands was fought
on the side of a ridge called Rullion Green, in 1666, between a party of armed Covenanters under Colonel Wallace, and a superior force of Royal troops commanded by General Dalziel.
The Covenanters, mostly men from the West of Scotland, had taken up arms in defence of what they considered their national and constitutional liberties;  but, fatigued by exhausting marches, and over-powered by numbers, they were defeated after making a brave resistance.  About fifty of them were killed, but many more were taken prisoner, and dragged into Edinburg, where they were punished with merciless severity.          
Battle-Song of the Pentlands
     This day must set in blood!
       Each true man to his post! 
Strike for Christ's Crown and Covenant,
       And God be with His host!

      Though few and faint we be,
    And the tempests wildly blow.
   Yet here, upon this naked heath,
        We fearless dare the foe.
       Long hath the tyrant raged,
   And the people have been dumb.
  Sword of the Lord I avenge the past,
       And free the time to come!

          Not for the fading leaf,
   That decks the conqueror's head
   Nor sinful thirst for blood or gold,
          Our feet have hither led,
          We combat for our rights,
            For our heritage Divine.
O Lord!  look down from heaven in love,
           And visit this Thy vine. 

       Our homes in darkness lie,
   And our pleasant fields are waste,
     And our fathers and our brethern
      Like beasts of prey are chased.
       Our priests are driven forth,
       And our temples are defiled;
And the house of God must now be sought.
             Far in the desert wild.

     And now that, front to front,
  We have met the tyrant's horde,
Woe be to him that slacks his arm
        Or turns away his sword!
            Better to fall in fight
        For the charter of our land,
     Than pine in bondage and in fear,
          A crouching hunted band.

           And if we fall, this hill
         Like Lebanon shall grow,
    And other times in gladness reap
          What we in trouble sow,
         And where our ashes rest,
          Beneath the heather sod,
    The youth of Scotland shall renew
          Their Covenant with God.

         This day must set in blood!
          Each true man to his post!
  Strike for Christ's Crown and Covenant,
          And God be with His host!

NOTE:  The Covenanters who were killed in the Battle of "Rullion Green" are buried in a tomb in the village of "Pentland".