History of the 5th Connecticut Regiment 1775-1783

(Prepared in 1978 by F. Lee Betz from “Record of Service of Connecticut Men in the War of the Revolution — Compiled by Authority of the General Assembly under the direction of the Adjutants General.)

The regiment was initially formed in May 1775, when the Connecticut legislature created six regiments in response to the hostilities begun at Lexington and Concord. The regiment was then composed almost entirely from officers and men of Fairfield County. David Waterbury of Stamford was named first colonel. His fellow officers hailed from Greenwich, Stamford, Stratford, Fairfield, Norwalk, Ridgefield, Danbury, Greenfield Hill, Newtown, Ripton, New Fairfield, North Stratford and Redding.

In June 1775, the 5th was sent briefly to New York City, but by July began its northward trek along the Hudson River with town other Connecticut Regiments to invade Canada and secure Lakes George and Champlain. The regiment received its first hostile fire from a force of Indians just prior to laying siege to the British fort at St. John’s. Together with New York troops they engaged in a long siege that eventually led to the capture of Fort St. John in early November. Brigaded under General David Wooster, the 5th then joined the van of American forces under General Richard Montgomery and marched to Canada ten days later.

Although enemy action caused some casualties the regiment suffered greatly from severe weather and large numbers were discharged early due to sickness. Because they were enlisted only until years end, the unit was mustered out by December 13, although some members remained in Canada to form part of a provisional regiment under David Wooster. These men participated in the ill-fated December 31 attempt by Montgomery and Benedict Arnold to storm Quebec City. Only a handful survived the failed assault and the subsequent retreat through a brutal Canadian winter.

A second 5th Connecticut formation mustered for Continental duty in early 1777, when Congress recognized the inadequacy of one-year enlistments and provided for a greatly expanded 88-regiment army to be raised for continuous service until the end of the war. Eight regiments would come from Connecticut. Philip Burr Bradley was named colonel of the new 5th Connecticut and served until the beginning of 1781. While the regiment was forming (many were in quarantine from smallpox vaccination), British General Tryon launched his successful raid on the patriot supply depot at Danbury in April 1777. Colonel Bradley and perhaps fifty raw recruits in the area supported the local militia under General Benedict Arnold to engage the redcoats at Ridgefield. Private Bradley Dean was killed, and Sergeant Clement Lloyd died in action next day as the redcoats returned to their ships off Compo Beach in present day Westport.

By June, the Connecticut regiments were encamped at Peekskill, New York, where they became part of the defense force in the Highlands and were put to work constructing fortifications at Constitution Island. After Washington’s main army suffered defeat at Brandywine Creek in Pennsylvania, the 5th was one of four Connecticut regiments rushed southward to Washington’s aid under General McDougall. They arrived in time to participate in the action at Germantown, where they formed part of General Nathaniel Greene’s division to the left of the American line. Bradley’s regiment distinguished itself and suffered heavy losses including a large number of prisoners.

In mid-October 1777, the 5th was assigned to the Brigade of Connecticut general Jedediah Huntington and would serve under this durable officer for most of their remaining history. They tramped into Valley Forge that December and lost over 35 men to cold, disease, and starvation over that legendary winter. The survivors were taught the new drill by Baron Von Steuben.

The 5th was present at the Battle of Monmouth on June 28, 1778, and distinguished itself under Bradley and Huntington in the second line that Washington formed after General Lee’s precipitous retreat. They then went into camp with the main army at White Plains, New York until winter when the Connecticut brigades quartered in huts at Redding Connecticut. Patrols were maintained along the Long Island sound coast. Suffering from cold and starvation, their pay in arrears, the men of Huntington’s brigade assembled under arms at Redding and determined to march to Hartford and petition the legislature for redress of their grievances. When addressed kindly and firmly by General Putnam who commanded at Redding, the troops dispersed to their huts and remained quiet until spring.

With hostilities in the north now reduced to skirmishes and raids, the 5th spent its remaining history in Washington’s defense force erecting fortifications at West Point. During the summer of 1779, the unit was dispatched as part of two Connecticut brigades to the Connecticut coast in response to a British assault that left Norwalk, Fairfield and parts of New Haven in ashes. Lead units clashed with redcoat units as they withdrew to their shipping after torching Norwalk. The 5th’s light infantry company under Captain St. John was temporarily assigned to General Anthony Wayne’s light infantry brigade and participated in the glorious midnight bayonet assault that captured the entire British garrison at Stony Point on July 14, 1779. As part of Wayne’s right column in taking Stony Point, Lt. Edward Palmer was wounded in the arm and thigh, while Ensign Samuel DeForest (of Wilton) behaved gallantly.

On December 1st, the regiment was assigned to winter quarters in Morristown, New Jersey and occupied the first line of three in the general line of battle. After suffering a much more severe winter than at Valley Forge, the regiment was detached to serve on outpost duty providing a buffer between Washington’s main army and British foraging parties from Manhattan. Other small detachments served on the northeastern Pennsylvania frontier to protect settlers in the Connecticut grants at Westmoreland from Indian attacks. The full Connecticut Division marched back to the Hudson Highlands in June 1780, and took up post near Robinson’s Farm on the east side of the Hudson. The 5th then wintered at Connecticut Village, a series of log huts constructed opposite West Point, until Colonel Bradley’s formation was disbanded in December 1780.

Because Continental army troop strength had fallen to less than half 1777 levels, Congress consolidated the remaining men into a smaller number of units in the field. Effective January 1, 1781, Colonel Bradley retired and remaining soldiers of the 5th became the core of the new 2nd Connecticut regiment. The third and final formation of the 5th Connecticut was then formed from the officers and men of the old 1st and 8th regiments — both veteran units tracing their history back to 1777. Under new commander Colonel Isaac Sherman the regiment consisted of eight battalion companies and one light infantry company for a total of 483 men.

During the spring of 1781, the light infantry companies of Connecticut regiments were detached and the battalion companies participated in several expeditions around New York City under General Washington. When Washington moved half his army south to rendezvous with the French at Yorktown, two of the 5th’s companies were assigned to General Lafayette’s command. The bulk of the regiment remained in the Hudson Highlands to decoy the British command in New York from determining Washington’s true intentions. The two companies that marched off to Yorktown were selected to participate in the famous midnight attack on British redoubt #10, in which Sergeant William Brown of Stamford earned the highest Medal of Merit awarded to the ranks during the entire war – a purple heart. Only three were given. Another 5th Connecticut soldier, Sergeant Jeremiah Keeler of Ridgefield, was given a ceremonial sword by Lafayette himself for his bravery in the assault.

After the British surrender at Yorktown, the reunited regiment wintered again at Connecticut Village near West Point and participated in the large celebratory parade in review with French troops at Verplank’s Point. With hostilities near an end the army was further consolidated and the men of the 4th and 5th regiments were assimilated into the other three regiments. On January 1, 1783, the regiment was disbanded for the final time and its remnants joined Bradley’s veterans in the 2nd Connecticut. In June they were all furloughed when the Continental Army was disbanded.

In 1975, exactly 200 years after its first formation, a group of Ridgefield men received a charter from then Connecticut Governor Ellla Grasso to reform the 5th Ct. as an honorary unit. On October 30, 2004, the re-enactor unit celebrated its 30th anniversary as living monuments of the patriots who fought for independence in George Washington’s army.

Lineage and Honors

1 May 1775 Regiment formed, commanded by Colonel David Waterbury
14 June 1775 Regiment adopted into the Continental Army
July-Nov. 1775 Siege of Fort St. John, Canada
13 November 1775 Capture of Montreal, Canada
13 December 1775 Regiment disbanded at Fort Ticonderoga
1 January 1777 Regiment reestablished, commanded by Colonel Philip Burr Bradley
April 1777 Connecticut Campaign, Battle of Ridgefield
Apr. – Sept. 1777 Hudson Highlands Defense
October 1777 Defense of Philadelphia Campaign, Battle of Germantown
12 Nov. 1777 Fort Mifflin, Pennsylvania
Winter 1777-1778 Valley Forge
26 June 1778 Battle of Monmouth
Winter 1778-1779 Redding Ridge, Connecticut
15 July 1779 Battle of Stony point (Light Infantry Company)
Winter 1779-1780 Morristown
June 1780-1782 Hudson Highland Defense
1 January 1781 New York Campaign, Morrisania
January 1781 First Regiment reorganized from First and Eight Regiment, commanded by Colonel Issac Sherman
6 July 1781 Battle of Green Springs, Virginia (Light Infantry Company)
Sept. – Oct. 1781 Siege of Yorktown (Two Light Infantry Companies)
1 January 1783 Fifth Connecticut Regiment disbanded at West Point
October 1974 Fifth Connecticut Regiment recreated by Dennis Ambruso, Eric Chandler, Otto DePeirne, Jim Freebairn, Rick Gillespie, Fred Glissman, John Passiglia, Tom Pearson and James Purcell, Jr.