The local cat boat fleet resumed informal racing at Sing Sing during the mid 1880s.  Starting in ‘85, half a dozen boats began a series of races for prizes that lead to the formation of the Sing Sing Boat Club three years later. The new Boat Club flourished in their first year and, side by side with the Shattemuc Canoe Club, enjoyed a golden year of sailing.   The following year, 1889, the club would be incorporated, change its name to the Sing Sing Yacht Club and lease its own clubhouse.  Enthusiasm and the number of new sail boats grew apace.  The Club absorbed many members of the Shattemuc Canoe Club and added canoeing to their boating activities.
 

The firing of a gun on the Camilla started the fleet off, and they got away well together with the exception of the Lena, which was very balky and could not be gotten up to the mark in time to take any part in the race.  The Beatrice came to grief before going one-half over the course by the breaking of her rudder.  Shortly afterward the Foam followed suit and also retired from the race in good order, though she met with no other mishap than falling too far to the rear to retrieve her proper place and stand any chance of victory.  This left the race between the Cora and Alice.  They fought the billows valiantly, and the mariners aboard them resorted to all the tricks of the trade to squeeze speed out of them.  After a very pretty struggle the Cora passed the home stake boat at 5:20, her elapsed time having been 2 hours 27½ minutes, her corrected time according to the time allowance – the Cora allowing here 4 minute and 25 seconds – being 2 hours and 23 minutes.

It is probable several other races may be arranged to take place some time during the summer. -- Democratic Register 06-27-1895

The Yacht Race.  In the afternoon there was a light breeze from the southeast, which gave indications of freshening up, and the following boats prepared once more to cross the line.  The time allowance was calculated upon the basis of one minute to the foot.

YACHT-OWNER         LENGTH    TIME AL.
                                                         M.S.

Aller-Philip Samstag….. 25.08……..0 00
Cora-Benjamin Smith… 23.11……..1 45
Pauline B-James Smith...22.06 …….3 10
Bon-Edward Delevanty..20.10……..4 50
Lena-Peter Smith………18.05……..7 15

The run out was a blanketing match between the Pauline and Aller, as the latter quickly picked up and passed the rest and tried to pass the Pauline to lee-ward.  This she failed to do and the Pauline hauled past the stake-boat ahead .

Then the beat down to the lower stake began and the Pauline still held her lead.  About five hundred yards below the stake-boat the crew of the Aller began to throw out their ballast carried under the flooring.  For about ten minutes it rained bricks and cobble stones and the boat began to loom up and walk along faster in the light breeze, which had a tendency to come around to south-southwest. The crew of the Pauline exercised themselves in emptying their sand bag in the meanwhile.  The Bon and Cora were quite a distance behind in the order named, and the Lena was virtually settled as far [as] the race was concerned.

The Pauline got around the lower stake- boat, off of Scarborough, about seventy-five yards ahead of the Aller, the Bon and Cora following some two hundred yards in the rear.  In the run up with booms to port the Aller picked the Pauline up off of Mt Murray, and the run up to the inner stake-boat was nip and tuck and the crews on either boat could have jumped on board the other craft so close were they together most of the way up.  The Pauline finally got a little puff of air that lifter her past the stake-boat about ten yards in advance of the Aller, and the same shoot of wind sent the Cora past the Bon off of Blakeslee’s new foundry.  The Cora got around the stake-boat about three yards ahead, and the Aller had caught the Pauline and run out to the upper stake-boat and went around about seventy-five yards ahead.  The Cora held about the same distance behind the Pauline as at

the inner stake, but was leading the Bon by eight yards or so.  The breeze was now freshening up and the Aller appeared to be running away from the Pauline, but whereas the former made a short leg in order to go around the lower stake-boat the Pauline held on the starboard tack and the boats rounded the lower stake-boat in the following order, unofficial time, although it shows the lead held by each craft:

YACHT          H. M. S.   YACHT   H. M. S.
Aller….…...5 20 01   Cora……5 25 03
   Pauline……5 20 36   Bon…….5 26 07  

The run up from the lower stake-boat was characterized by the Aller passing the Pauline, but she did not get far enough ahead to beat her competitor and allow her the three minutes and ten seconds due her.  The Cora and Bon came in as shown below.  It is due to the owner of the Cora to say that he did not expect his craft to win in the wind that was prevailing, and had the race taken place on the ensuing morning the result would have been entirely different as far as the Cora was concerned, as it was blowing a stiff northwester.  The following is taken from the official time and gives a complete summary of the race:

                                              ELAP’D  COR’D
YACHT      START   FINISH     TIME      TIME.
Pauline B…3.00.58    5.38.25     2.37.27   2.34.17
Bon ………3.01.05    5.45.19     2.44.14   2.39.14
Cora………3.01.18    5.44.16     2.42.58   2.41.13
Lena...…….3.01.28    Withdrawn
Aller………3.01.37    5.37.11     2.35.34

Thus the Pauline B beats the Aller 1 minute and 17 seconds on time allowance. The Aller beats the Cora 5 minutes and 39 seconds allowing time allowance, and the Bon by 3 minutes and 40 seconds corrected time.  The Aller’s actual time over the course makes her beat the Pauline B by 1 minute and 53 seconds. --The Republican 10.07.1886

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Sport on the River.  After waiting a week, our local yachtsmen were favored with favorable breezes on Tuesday last for settling their differences as to speed and had their regatta.  There were seven  [sic] entries as follows:

                          FIRST CLASS
     Yacht.              Owner.          Length.
Whileaway……..William Walker……27.07
Aller Philip……..Samstag………….. .25.06
Cora…………….Benjamin Smith…..  23.11
Pauline B……….James Smith……….22.07

                      SECOND CLASS
Beatrice…………Lorenzo Sniffin…..19.00
Lena…………….Peter Smith…….….18.06

At the signal for the start, the little fleet got away in a bunch and as the wind was blowing from the southeast they flew away on the port tack with the crews sitting well up to windward keeping company with the sand bags taken along for ballast.  They each strove to steal the wind of their nearest adversary and pocket it, and in many instances were successful.  By the time the prison was reached, the respective merits of the boats began to tell and the fleetest took the lead, leaving the others to fight it out amongst themselves. The course for the first class yachts was from the Upper Dock toward and around some buoy off Dobbs Ferry and return, and for the second class yachts to and around the Tarrytown buoy.  William Tallcott’s twenty-one foot yacht, Daisy, started with them, but did not go over the entire course. The yachts were all well sailed and good time was made.

When the course had been completed, it was found that the Aller had beaten the Cora in 4:20:08, winning in 2m 36s, corrected time.  The first prize, a preserve dish present by Col. Franklin Brandreth and Collector Charles S Raymond, was given the Aller. A handsome ice-water pitcher from the same donors was given the Cora.

In the second-class race the Beatrice defeated the Lena in 3:16:22, winning by 9m. 26s corrected time.  A silver card receiver was given the Beatrice.  All the other yachts were badly distanced. The Whileaway was all of ten minutes behind the Pauline B.

The Judges were Charles S Raymond, Capt. Charles Hilbert, and Robert T Dennis.

It is intimated that these yachts will have another race soon in Haverstraw Bay to try conclusions under different conditions, as the defeated ones of Tuesday think they can change the result.

In the evening the victory of the Beatrice was celebrated at the Upper Dock by the letting off of fireworks, in the enjoyment of which the whole village participated, for the rockets went very high -- The Republican 07.23.1887

The Sing Sing Yacht Club.  On Friday, October 14^th 1887, a trio of Sing Singers found shelter in the lee of the plot house of the little steamer that was running in the place of the Nyack-Tarrytown ferryboat Tappan Zee, on its return trip from Nyack.  They were William W Washburne, Charles Schade and Robert T Dennis, who were returning from a trip to Nyack where they had just put the yachts Lotta and Alice J in winter quarters.  In the course of conversation the subject was broached of forming an aquatic organization in this village.  Within two weeks what was the foundation of the Sing Sing Yacht Club was formed under the name of the Sing Sing Boat Club. -- The Republican 06.06.1889

 

Cat-boat Race  There was a race for cat-boats, owned in this vicinity, on Tuesday last which, owing to a stiff northwest wind and high sea, was an exciting event.  The entries were the Aller, owned by Philip Samstag; Cora, Benjamin Smith; Pauline B, James Smith; Lotta, Washburne Bros.; Alice J, Schade and James.  The start was at about 1:30 P.M. and they sailed over a triangular course from the Upper Dock to the Point, near the channel, to Scarborough, and thence back to the Upper Dock, this to be sailed over twice.  They started off in the following order: Aller, Cora, Pauline B, Alice J, and Lotta.  Shortly after the start, several of the little fleet came to grief.  They were all going with full sails and the Lotta unstepped its mast and presently broke its forestay at the lower stake boat.  When out in the channel the Cora broke a side stay, missed stays, and had to withdraw from the contest.  All the others remained in.  The Alice J when down by Scarborough, came near being swamped by the big swells from the steamer Albany and came home disabled.  This left only the Aller and Pauline B in the race and the former finished in 2:10:40, the Pauline B being 5:52 by corrected time, behind her.  The first prize was a whip pennant and American yacht ensign, and the second a silver ice-water pitcher, both presented by Collector Charles S Raymond.  The Judges were Robert T Dennis and Cady Champlain. -- The Republican 10.15.1887

1888 Advertisement for Allcock’s Porous Plasters linking a winning product with local enthusiasm for sailboat racing.

Twenty Years Ago  At the annual meeting of the Sing Sing Boat Club, the following officers were elected: Ralph Brandreth, commodore; W W Washburn, vice-commodore; William Henry Rowe, secretary; Joseph Thompson, treasurer; Benjamin R Smith, measurer. --The Democratc Republican 03.03.1908

Brief Mention The Sing Sing Boat Club are making preparations for a regatta to take place off this village on Decoration Day.  The regatta committee has the matter in charge and will endeavor to make it a notable aquatic event in this vicinity.  The club is making its new quarters in the Brandreth boat house attractive and will have a float put out as soon as it is built for them. --The Republcan 04.07.1888

The Yacht Race.  The yacht race, which for want of wind was postponed on Memorial Day until Saturday last, took place then, and the little craft had a roaring southwester.  The following were the entries:

	SLOOPS
Name	Owners
Waif	S W Edgerton, E T James
Lurline	Isaac Washburn
	CATBOATS
Aller	P Samstag & Brother
Cora	B R Smith & Brother
Pauline B	James Smith
Lotta	Washburne Brothers
Helen B	Franklin Washburn
Alice J	Charles Schade

They made a lively looking fleet as they were tacking about, south of the starting line, waiting for the signal to go.  The regatta was in charge of Acting Commodore B S Gibson, who at the half past one o’clock fired the first gun for the skippers to get in readiness to cross the imaginary line between a stake boat anchored off the club house and the end of the pier.  So far everything went well, but when it came to firing the gun to start the fleet, the patent primer simply flashed and succeeded in effectively spiking the gun.  None other being at hand, the Acting Commodore made use of the lung power and yelled to them to “go” which they did, though it appeared, after the race that there was a good deal of confusion thus occasioned, as

some were waiting for the gun to be fired, while the others were making time toward the first stake boat off the end of Croton Pont.  One noticeable instance of this was the sloop Waif, which virtually drifted stern first over the line and for about five minutes lay with her nose in the wind and sails flapping.  Her crew did not then realize they had crossed the line, and that all that loafing was counting in their time and that she should be on her way.  Finally she got under way and started off.  This mistake cost her the race.

As the little yachts bounded on over the course – which was the club’s triangular one -- from the club-house to Croton Pont, to a boat anchored off Scarborough, and thence home again, to be sailed over twice, making a run of about twelve miles – they presented a most beautiful sight.  Men and sandbags were piled up high to windward, while even then the lee rails were well under water.  Every now and then a huge swell would throw a shower of spray over the crews, but they did not mind that, they expected to get wet.  Soon after starting, the Helen B struck a sunken shad pole, and was so disabled that she had to retire from the race and return to dock.  When the race was almost over the Alice J, sailed by her owner, Charles Schade, when sailing handsomely near the Scarborough boats, cracked her mast near the deck and had to let down her sail and retire from the race.  She came back to the dock under shortened sail, with wind and tide in her favor. 

Meanwhile, the Aller and Pauline B both having broken their gaff throat were having a pretty race by themselves each straining every nerve so to speak to win the pennant and prize.  The Waif had picked up the Lurline and passed her some distance, but the time she had to allow her and that which she lost at the start were too much to overcome.  The pretty Cora did not loaf any, and the natty Lotta, had she had a larger crew and more sandbags would have done faster work.  She was well sailed, but the lack of ballast was evident to all who viewed the race. At last the fleet came home, the Aller leading with a big white bone in her teeth, followed by the Pauline B, Cora, Lotta, Waif and Lurline, in the order named.  --The Republican 06.09.1888