Most of the people who lived on Hill Road, Jockey Hill and in Stony Hollow were Irish. (The thriving stone trade encouraged the growth and flourishing of the area.) The St. Ann's Catholic Church was opened on Jockey Hill in 1869 and a school began operating soon afterward. AS a youngster Historian Harry Siemsen recalled:

At the school one of the first things was to put up the flag, there was a flag pole out in front of the school. And then a regular chore was to go after a pail of drinking water for the school. That was usually a hike of about a mile or so. And of course we had a sanitary dipper there, we all drank from the same thing. We were normal children so it didn't bother us too much. We put wood or coal in the stove, the stove was in the center of the room. Besides learning the three R's we learned how to play `shinny',' duck on the rock', `curly over'. We found out that sumacs make good shinny sticks. Of course today they call them hockey sticks but that time was it shinny. We found out that if you climb young saplings you can swing off in the air and they will lower you to the ground by bending over. We used to take the sumac, the sumac has a curved root, you get a straight stem of the sumac and then with the curve, that would make the hook, you know, of your hockey stick.

Then of course for pucks, we used a tin can. Unfortunately, the tin can got battered down to a lump of metal. One of the boys got hit with the puck, it cut this whole lip open. So after that we had to use a piece of wood or otherwise we had to stop.

Though we had plenty of room to play ball we didn't. Balls and bats cost money and we didn't have any. Another thing, you learned to set your lunch pail near the stove in winter so the sandwiches didn't freeze, if you had sandwiches. Usually, there was no milk, it was just sandwiches. And of course some kids they would just have bread and lard or something that they put on or black strap molasses Another thing we learned going to school was to track rabbits to their dens in the stone walls and rubbish piles. You learned to dig'em out then have rabbit stew for supper. I ain't kidding you, these pretty little bunnies that the children today admire meant meat in the pot for us. In the morning some boys were lucky, they got time off from school to carry a lunch. They'd go home, get their father's dinner pail and take it to them in the quarries.

Another little incident, in order to instruct the students in our government, on election time the teacher resolved to have an election in the school. We were not only supposed to elect the most popular boy in the school; this was before women had the right to vote, so girls had nothing to do with this, this was just purely boys, we were supposed to elect a whole town list of officers. Well, comes the morning, there were two brothers selected to he candidates for the most liked boy in the school. One was a democrat, the other a republican. One was Charlie McCaffery, we knew him as `Pug' and the other was `Goosie' that was John McCaffery. John was a better politician than `Pug'. He went to the republican candidate and said, `Now listen, we're going to have an election down at school, I want to swing it your way, give me some money and I'll get some candy.' Nope, he wouldn't have anything to do with it. So he went to the other candidate Bud Brophy, and Bud gave him about fifteen cents which he used quite prudently in the candy store or the general store where they sold penny candy and about a half an hour before we went in to vote, which was to be after recess, `Goosie' called us all over to a vacant house that stood near by and he divided the candy out between us. So we went in to vote eating `Goosie's' candy. You know who won the election.

Harry Siemsen's farm neighbored along a heavily worked quarry known as Terry's Ledge (today the site of Camp Woodcliff). During the first half of this century, this area was mined on a smaller scale by local stonemen. Siemsen recalled that:

Quarrying was a tricky and involved business that the quarrymen had to know well. The bluestone was beneath layers of soil, clay and stone. This overlay material had to be stripped. After stripping down to the block of good stone the quarryman then looked for the natural vertical joints called side seams running north and south, and then the east and west joints called headoffs. He then had to know how to delicately tap wedges into the horizontal seams so that he could pry up perfect slabs of bluestone called lifts. It was a precise operation and he had to know how to use his tools well: the hammers, points, drills, wedges, crowbars, plugs and feathers, shovels and picks. The quarrymen were always taking a gamble, as they never knew if they would get a good block, or, if they did, whether or not their `stone boats' or wagons, would make it down the side of the mountain. Also, the quarrymen had to pay `quarry rent', generally 5% of the selling price to the landowner . Cartage, tolls, and rent where due were deducted at the time the stone was paid for at the stone dock. One time after the deductions for a two horse load of stone at the dock, there remained $ .76 for the quarrymen. Around 1869 intense competition and cutthroat operations, coupled with a slowing of the Canal economy (which being challenged by railroads) began to have impact on the Bluestone workers.

According to the Daily Freeman in May 1876:

Unified by ethnicity, trade, low social status and poverty, the Irish quarrymen banded together and became a strong political machine on Jockey Hill. This boisterous group overwhelmed the older, more staid traditional government of property owners. The Irish leaders (sometimes known as Molly Maquires, and also called Red Shirts because they always wore red long underwear) used strongarm tactics to support corrupt officials of the Democratic Party. In return, the loyalty of the Irish was rewarded by the Democratic politicians but not out of the gratitude of their own hearts or their own pockets. Instead, tax money was used to finance an expanded "Pauper List" providing merchandise or cash to each who was owed a favor. This list grew to such an extent that by 1879 the Town of Kingston's expenses for assistance to the poor were $15,976.00 compared to the Countywide average town cost of $484.00. Needless to say, property owners had had enough. (Kingston Daily Freeman, 13 February 1879)

After a bitter and violent election night in 1879, the State commenced a long and thorough investigation into the corrupt activities of the odious Town of Kingston. This led to the demise of the Democratic Party and the merciless division of the Town. "The Undesirable Town of Kingston-The petition which circulated about the division of the present territory of the Town of Kingston and its apportionment into other towns. was sent to the State Legislature and spoke strongly in favor of it. It said when he old town was divided it left the present Town of Kingston a territory small in extent, feeble in population, and mountainous in character, rocky with a thin sterile soil, poorly watered, and with scarcely an acre of tillable or grazing land. No hay, grain, vegetables, poultry or cattle could be produced for sale. The flagstone quarries, which had been for many years the main source of revenue, were nearly exhausted. The population had diminished from year to year; the young people such as could get away, moved to other places where they could make a living. The taxes were now so great and heavy, being nearly 107 on a fair valuation, as to bankrupt them, their homes being confiscated. In fact, they are too few in number, only 73 in 1881, and too poor to support the machinery and expense of a separate ownership."

The town struggled and survived and became the smaller, quieter force intended by State officials. Bluestone quarrying continued on a lesser scale, typically by local residents who also farmed and did "piecework" at none as a means of support. During the early part of the century "taking" summer boarders became a popular pastime with town people as well as a boost to the economy.

For the Irish families and other Catholics who remained in Sawkill, St. Ann's church continued to be an integral part of the community. On property acquired in 1868 for a cemetery, a second St. Ann's Church was constructed c.1878. The original Church on Jockey Hill was then converted to a two-family home known as the "long shanty". In 1913 the second St. Ann's was destroyed by fire and rebuilt the same year on the old foundation.

The outdoor shrine was built in 1944 when the parish was 75 years old, and St. Ann's became famous throughout New York, New England and Canada. (Kingston Daily Freeman, 13 March 1883). Many people made pilgrimages to the shrine during the Feast of St. Ann particularly during, the novena held every year in August. (Kingston Freeman, 28 August 1913). Mass was celebrated outside on the stone altar and chairs set up on the grounds for the many people who attended. It is said that a crippled girl was cured at the shrine during one of these services when she stood up from her wheelchair and walked to the altar, St. Ann's was assigned as a mission church of St. Catherine 1,aboure Parish in Lake Katrine in 1961. It was not popular change among Sawkill's communicants, and when the Church was closed altogether in , local residents formed a group to preserve the Church and its traditions Between 19211922 a new school was built (present site of the Town Hall but only because the previous school on Jockey Hill had burned down.

Growth of the town was stymied until the end of W.W.II because of its relative isolation and the slow development of a good road system. Due to the establishment of new and expanding industry in Ulster County during the 1950's and the 1960's, the town experienced the national trend of suburban growth. In recent years, it has also had to grapple with important environmental issues and the question of a return to Bluestone quarrying. But its present-day scale, established approximately 100 years ago by the State, allows the town to retain its essential rural, small town character and effective local government. (Kingston Daily Freeman, 7 June 1969).