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Whaleboat Warfare

Americans and British cross Long Island Sound to stage surprise raids

By George DeWan | Staff Writer

At 1 p.m. on May 23, 1777, the Patriots began striking back at occupied Long Island.

Leaving Guilford, Conn., with 170 men in 13 whaleboats, escorted by two armed sloops, Lt. Col. Return Jonathan Meigs crossed Long Island Sound, skillfully avoiding armed British vessels. The raiding party landed about 6 p.m. on what is now Hashamomuck Beach in Southold, one of the narrowest points on the North Fork.

What took place early the next morning is commemorated on a granite monument near the Old Whalers' Church in Sag Harbor. The Battle of Sag Harbor was worth a monument.

Meigs and his troops -- men like Elnathan Jennings of Southampton and Christopher Vail of Southold -- carried their boats across 300 yards of land, re-entered the water and rowed across Southold Bay and Shelter Island Sound, landing at midnight on the beach four miles west of Sag Harbor.

At 2 a.m., Meigs struck, taking the British, many of whom were drunk, completely by surprise. The raiders burned 12 brigs and sloops, killed six men and captured 90, then returned with their prisoners the same way they came. Without losing a man, they were back in Connecticut 25 hours after they left.

This was whaleboat warfare.

Long Island Sound, however, was a two-way thoroughfare. In fact, the first cross-Sound raid was made by the British. On April 25, 1777, Gen. William Tryon, the colonial governor of New York, led a 2,000-man force across the water to destroy part of Danbury, Conn. The sortie by Meigs was in retaliation for Tryon's raid.

These whaleboats were of the type used for offshore whaling, though many were probably built solely for the purpose of revolutionary warfare. They were fast, and they were double-ended, for two-way rowing and for better handling in rough surf. Light enough to be carried on men's shoulders, the boats could be fitted with a single sail, and usually carried a small, swivel cannon in front. Six or eight oars were standard.

Most of the Patriot raids were made in Suffolk County, where anti-British sentiment was strongest. British forts at Lloyd Neck (Fort Franklin), what is now Fort Salonga (Fort Slongo), Mastic (Fort St. George) and Sag Harbor were successfully attacked. However, a raid on Setauket was repulsed by the British. The British made later raids on Greenwich, New Haven, Fairfield, Norwalk and New London.

The most spectacular Patriot whaleboat raid was made on Fort St. George in Mastic in the fall of 1780, led by 26-year-old Maj. Benjamin Tallmadge, Gen. George Washington's spy chief. The strategically placed fort had been built a month or so earlier by Loyalist troops from Rhode Island at the Manor of St. George on Smith's Point. The triangular fort included two houses from the manor in two corners, and an additional fortification in the third. The fort served as a supply base for British forces.

At 4 p.m. on Nov. 21, 1780, Tallmadge and 80 men shoved off in their whaleboats from Fairfield, Conn., landing at 9 p.m. at Old Man's -- now Mount Sinai. After a rain delay, they began their march the next day, arriving at the fort before sunup Nov. 23. With the prearranged cry of ``Washington and glory!'' three detachments attacked the fort, and it was quickly taken. But the main body of the British garrison was in the two houses. In a later memoir, Tallmadge told what happened next:

While we were standing, elated with victory, in the centre of the fort, a volley of musketry was discharged from the windows of one of the large houses, which induced me to order my whole detachment to load and return the fire. I soon found it necessary to lead the column directly to the house, which, being strongly barricaded, required the aid of the pioneers with their axes. As soon as the troops could enter, the confusion and conflict were great. A considerable portion of those who had fired after the fort was taken, and the colors had been struck, were thrown headlong from the windows of the second story to the ground. Having forfeited their lives by the usages of war, all would have been killed had I not ordered the slaughter to cease.

Tallmadge then had his men turn the fort's guns on a nearby ship, burning it to the water line. Then they destroyed the fort. By 8 a.m. it was over. Seven Loyalists were killed or wounded and 53 officers and men captured. Tallmadge lost no men, and only one was wounded.

`All things were now secured and quiet,'' Tallmadge wrote, ``and I had never seen the sun rise more pleasantly.''

Tallmadge was not finished. Taking a dozen men -- including 33-year-old Caleb Brewster, who was Agent 725, the whaleboat captain in the Culper Spy Ring -- and mounting them on Loyalist horses taken from the fort, Tallmadge headed for the 300 tons of hay stored at Coram. He sent the main body of troops with the prisoners back to the whaleboats. Reaching Coram in an hour and a half, Tallmadge's men overcame the guards, set fire to the hay, and went on to rendezvous with his troops. They reached the whaleboats at 4 p.m. on Nov. 23. By midnight they had crossed the Sound and were back in Fairfield.

Although Washington was pleased with Tallmadge's work, and Congress passed a resolution praising him, Loyalists saw the Battle of Fort St. George in a different light. Here is an excerpt from a Dec. 2, 1780, news report in the Royal Gazette, a Tory newspaper:

Mr. Isaac Hart of Newport in Rhode Island, formerly an eminent merchant and ever a loyal subject, was inhumanly fired upon and bayoneted, wounded in fifteen different parts of his body, and beat with their muskets in the most shocking manner in the very act of imploring quarter, and died of his wounds in a few hours after, universally regretted by every true lover of his King and country . . . A poor woman was also fired upon at another house and barbarously wounded through both breasts, of which wound she now lingers a specimen of rebel savageness and degeneracy.