My grandfather was a duck trapper
He could do it with just dragnets and ropes
My grandmother could sew new dresses out of old cloth
I don't know if they had any dreams or hopes
I had 'em once though, I suppose, to go along
With all the ring dancin' Christmas carols on all of the Christmas Eves
I left all my dreams and hopes
Buried under tobacco leaves.
- Lyrics from Bob Dylan's Floater
The story of tobacco and the history of the Americas are intertwined.
Indians, it is believed, began using tobacco for smoking 2000 years ago. A Huron myth:
Huron Indian myth has it that in ancient times, when the land was barren and the people were starving, the Great Spirit sent forth a woman to save humanity. As she traveled over the world, everywhere her right hand touched the soil, there grew potatoes. And everywhere her left hand touched the soil, there grew corn. And when the world was rich and fertile, she sat down and rested. When she arose, there grew tobacco . . .
The Spanish were responsible for bringing tobacco to Europe on the mid-1500s, and cultivated tobacco rapidly became a major export of the Spanish islands (especially Cuba) and of Brazil. Thus began the era of tobacco use in southern Europe, as snuff or smoked, and especially smoked with pipes. It was variously regarded as a wonderful new medicine, as a pleasant habit, or as something to be forbidden.
The route to England was famously initiated via Sir Francis Drake via Sir Walter Raleigh around 1565. By 1620 40,000 lbs. of Virginia tobacco were sent to English markets, and lonely colonists could buy a wife for 120 lbs of it, and have her shipped over.
More fascinating details of tobacco history here, with the development of snuff, pipe-smoking, cigars and cigarettes.
But to get to the point, English settlers first cultivated tobacco in the Connecticut River Valley around 1630 (in Windsor, CT). The lucrative crop spread rapidly up the fertile valley to Massachusetts.
A Massachusetts blogger notes:
Connecticut tobacco farming reached it's apex in 1921, with over 30,000 acres planted with broad-leaf 'shade' tobacco, the large leaves of which are used primarily as the outer wrappers of cigars. Production declined in the 1990s, falling as low as 2,000 acres cultivated in 1992. Views on tobacco use have contributed to the plant's demise, the long wide fields covered with the shade tents no longer a staple of roadside scenery on a slow summer Sunday drive through the Valley.
As cigars became popular in the 1800s, CT growers gradually specialized in the more valuable shade-grown leaf which was dried and shipped to Cuba and elsewhere for cigar wrappers. The fields with their special drying barns remain a familiar sight in the CT valley.
A cigar history site explains it thus:
Soon there was a demand for higher quality cigars in Europe, and Spanish cigars were superseded by those made in Cuba, which was then a Spanish colony, where cigar production had started during the mid-18th century. Cigars, European smokers discovered, traveled better than tobacco. The cigar probably arrived in North America in 1762, when Israel Putnam, later an American general in the American War of Independence (1774-1778), returned from Cuba, where he had served in the British army. He came back to his home in Connecticut, where tobacco had been grown by settlers since the 17th century, with a selection of Havana cigars and large amounts of Cuban tobacco seed. Cigar factories were later set up in the Connecticut area, processing the tobacco grown from the Cuban seed. In the early 19th century American domestic production started to take off and Cuban cigars also began to be imported in significant
numbers. But cigar smoking did not really boom in the United States until around the time of the Civil War in the 1860s, with individual brands emerging by the late 19th century. By then the cigar had become a status symbol in the United States.During the same period, cigar smoking had become so popular among gentlemen in Britain and France that European trains introduced smoking cars to accommodate them, and hotels and clubs boasted smoking rooms. The after-dinner cigar, accompanied by glasses of port or brandy, also became a tradition. This ritual was given an added boost by the fact that the Prince of Wales, the future Edward VII and a leader of fashion, was a devotee, much to the annoyance of his mother, Queen Victoria, who disliked smoking.
Yes, it was Gen. Israel Putnam who brought the good Cuban seed to CT.

Photos:
1. Shade tobacco on a Massachusetts farm
2. Tobacco barn in New Thompsonville, CT, 1940
3. Tobacco barn at The Connecticut Valley Tobacco Museum in Windsor, CT
4. Connecticut's Revolutionary War hero Gen. Israel Putnam
5. Tobacco fields and barn in Hadley, MA