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The first and most famous Maypole erected in Massachusetts was the one put up by Thomas Morton at his colony of Merrymount in 1624. Morton was a well-educated English lawyer who had come to Massachusetts as part of a colonial expedition. Their colony, in what is now the city of Quincy, was initially called Mount Wollaston after Captain Wollaston, the commander of the expedition's ship. When Morton learned the captain was selling indentured servants to another colony in Virginia he encouraged the other servants to rebel. Wollaston fled, and Morton became the new leader of the calling. Preferring to call himself the colony's "host," he renamed it Merrymount.

Since Thomas Morton was an educated, literary type of guy, the name Merrymount had a variety of meanings to it. First, it indicated that the colony was to be a place of happiness now that Captain Wollaston was gone. Second, it was a play on the Latin word for the sea, mare, since the colony was on the coast. Ma-re-mount, get it? Finally, there was a sexual connotation to the colony's name, indicating it was someplace where the mounting (aka sex) was merry.

As May 1st approached the colonists Merrymount erected an 80' Maypole topped with a pair of deer antlers. They fired rifles and pistols in celebration, and Morton composed a poem that was nailed to the pole. Morton's poem mentions various Roman sea deities like Neptune, Amphitrite and Triton, and ends with these lines:
 

With proclamation that the first of May
At Ma-re-Mount shall be kept holiday

Morton and the other colonists invited the local Indians to join them at their celebration, particularly the Indian women. Beer flowed, people got drunk, and a good time was had by all. The Merrymount men sang a song that was composed in honor of the celebration. Here are some of the lyrics:
 

Drink and be merry, merry, merry boys;
Let all your delight be in Hymen's joys
Iô to Hymen, now the day is come,
About the merry Maypole take a roam. 

Make green garlands, bring bottles out
And fill sweet Nectar freely about.
Uncover thy head and fear no harm,
For here's good liquor to keepe it warm. 

Give to the Nymph that's free from scorn
No Irish stuff nor Scotch overworn.
Lasses in beaver coats come away,
Ye shall be welcome to us night and day

The "Hymen" mentioned in this poem is the Greco-Roman god of marriage, but again I am sure there is a double entrendre intended. 

I suppose if Merrymount had survived as a colony the history of New England would have been quite different, but it didn't survive. Shortly after the May Day celebration the Pilgrims from Plymouth Colony marched on Merrymount. They chopped down the May Pole, arrested Thomas Morton, and exiled him from New England. Morton made his way back to Merrymount in 1630, but most of the inhabitants had scattered by then. This time, the Puritans of Boston arrested Morton and burned Merrymount to the ground. Morton was sent back to England.

Back in England, Morton and his wealthy patron Fernando Gorges successfully sued to revoke the Plymouth Colony charter, but Morton's victory was short-lived because the English Civil War started. Morton fled from the chaos back to New England, where he died penniless in York, Maine in 1647. I believe he is buried somewhere in York, but I couldn't find a location for his grave. Perhaps it has been lost?

The New England Puritans and Thomas Morton came into conflict for three big reasons:

RELIGION

The Puritans followed a very strict version of Christianity that had rigid rules about how people should behave. They also didn't celebrate holidays like May Day or even Christmas, which they associated with the Catholic and Anglican Churches. Holidays were one of the things they were trying to purge from the English church.

Thomas Morton, on the other hand, was an Anglican who clearly enjoyed a good holiday. He was also well-educated and appreciated the ancient paganism of Greece and Rome. I don't think he was a practicing pagan, but he did enjoy the literature and mythology of the Classical World, as evidenced by his poem's references to Roman gods. This was quite common for educated people of his time. For example, Shakespeare's late romances Cymbeline, Pericles and The Tempest all include pagan gods.

The Puritans specifically cast Morton as a sinful pagan, calling Merrymount Mount Dagon (after the ancient Canaanite sea god) and saying the maypole was a modern version of the Golden Calf. Morton took up this mantle proudly. He titled his book about New England The New English Canaan, and urged readers to help protect the new Canaan from the invading Puritans.

SEX

As mentioned above, the Puritans expected people to follow very strict codes of behavior. Sex was intended for married couples. Morton and the settlers at Merrymount had a more relaxed view on these matters.

I think it is useful to note that many of the Puritan settlers were already married and brought their families to New England with them, while most of the Merrymounters were unmarried men with no problem enjoying the company of the local Indian women or possibly even marrying them. Intermarriage between European colonists and indigenous people was common in parts of the New World where the colonists were single men, but the Puritans took a dim view of this practice.

Some historians have also suggested that homosexuality may have been tolerated at Merrymount. For example, the authors of the Boston History Project's book Improper Bostonians point out that Morton mentions Jupiter, the king of the gods, and Ganymede, his male mortal lover, when writing about Merrymount. Of course, Ganymede was also Jupiter's cupbearer so he may have been mentioned because of his connection with getting drunk. Still, male homosexuality was somewhat tolerated among educated Englishmen like Morton. For example, the character of Antonio in Shakespeare's Twelfth Night is clearly in love with Sebastian, something the other characters do not question.

Morton himself never married, for whatever reason, so he would have personally benefited from "hosting" a sexually liberal colony.

MONEY

The Merrymounters were trading with the local Indians for beaver pelts, which brought them into direct conflict with the Puritans, who wanted to corner the trade in pelts. Morton and his men were also giving the Indians guns in return for the pelts, which the Puritans definitely didn't want. This just gave the Pilgrims one more good reason to shut down Morton's colony.
 

Peter Muise

http://newenglandfolklore.blogspot.com/2018/04/the-maypole-of-merrymount-religion-sex.html