Although quite a bit is known of Anthony's life in America, little is known of his life in England. He is believed to have been born about 1619, and some sources list, without documentation that I have found, his parents as being Anthony and Sarah Dorchester. Since Anthony himself had a wife named Sarah, I hope the two men are not being confused. I tend to believe his parents are not yet identified.
We don't know when Anthony came to America, either. Some believe it was as early as 1633, but Robert Charles Anderson hasn't covered him in any of the Great Migration publications that I've reviewed, so until there is some verification we will have to leave that as unknown. His second wife, Martha Chapman, may have been from Digswell, Hertfordshire, England but that may not be a clue since the marriage took place in Springfield, Massachusetts.
Savage, in his genealogical Dictionary of First Settlers of New England, says that Anthony went to Springfield about 1649 (probably soon after the death of his first wife, Sarah) but had been at Windsor, Ct. for some years prior (he is listed as a founding father of Windsor) and may have been at Hingham before that. Children by his first wife were John, Mary, and James, and were likely born in Windsor between 1644 and 1647. (Therefore, it is possible that a father or grandfather of Anthonhy's would have been John.) It is possible that Sarah died in or from complications of childbirth, since 1649 would have been about the time she would likely have had another pregnancy. With three small children to raise, Anthony needed a wife quickly, and less than three months after Sarah died, he was married to Martha Chapman Kitcherel, who was either from Digswell as indicated above or from Rolvenden, Kent, England. Apparently the jury is still out on her origins. Martha had children from her marriage, so it must have been a lively household as three more Dorchesters, Benjamin, Sarah and Hester, were added to the family. Martha died December 17, 1662 and Anthony next married Elizabeth possibly Cummins, his wife for the last 21 years of his life. She must have been an amazing woman to raise so many children who weren't "hers" by birth!
Anthony lived in very interesting times and the book "Colonial Justice in Western Massachusetts" tells at least one interesting story to indicate this. We don't generally think of slaves at that time period in Massachusetts, but it definitely was a fact of life. Jack ran away from his owner after one too many beatings, and 10 days later was at the Dorchester home. He asked for some tobacco, which the Dorchesters gave him, and then there was some sort of a struggle. It took Dorchester, his wife, and a daughter to subdue the man, possibly with the aid of a cutlass or possibly the cutlass "came out stiff" and therefore wasn't effective. When Jack was searched, he had in his pocket a knife belonging to Anthony. Jack was sent to jail until he was released into the custody of Lieut. William Clark. That night, the Clark house burned down, and Jack was soon found guilty of arson. He was sentenced to be hanged and his body to be burnt to ashes. It's not clear whether he ever stood trial for the events at the Dorchester home.
In addition to this story, Anthony and his wife were witnesses in a witchcraft case. It seems that an one time Anthony was working for Hugh Parsons, perhaps as a laborer, and he and Parsons each owned 1/4 interest in a certain cow. When the cow was killed, both men wanted the tongue. Dorchester got it, and it was put in the pot to be cooked but "mysteriously" disappeared. This was one of several incidents that got Hugh and his wife accused of witchcraft. Mrs. Parsons was tried in Boston for the death of her child, apparently believed to be witchcraft. She was found guilty but before she could be hanged she died in jail, apparently deranged. Mr. Parsons was also convicted of witchcraft but the General Court didn't confirm the conviction and he was allowed to leave Massachusetts. There's more to the Parsons story but our interest is in the Dorchesters, and it is interesting to see that both slavery and witchcraft touched their lives.
Anthony was a miller and a ferrier (ferryman? or farrier?) but he would have done at least some farming. We know he signed a petition in 1668 (along with a lot of other Allen ancestors and relatives) asking that the imposts, or tariffs, be lifted. We know that in 1663 he took an oath of fidelity, apparently routine, as part of the training band. He was on some local juries and was a selectman for Springfield. He was made a freeman of Springfield in 1661. He helped build the meeting house in Springfield, or at least was on a committee to supervise the building.
Anthony appears to have been relatively poor. He died without a will but his son John helped formulate an agreement with the heirs, including Martha, the daughter of Martha Chapman, who claimed that her mother had brought some property to the marriage. I'd love to find that inventory to see what was there when Anthony died August 28, 1683. Did he have a Bible and other books? Did he still have that cutlass? I'll keep looking!
The line of descent is:
Anthony Dorchester-Martha Chapman
Sarah Dorchester-Joseph Stebbins
Martha Stebbins-Samuel Lamb
Eunice Lamb-Martin Root
Martin Root Jr-Ruth Noble
Ruth Root-Samuel Falley
Clarissa Falley-John Havens Starr
Harriet Starr-John Wilson Knott
Edith Knott-Edward Allen
Richard Allen-Gladys Holbrook