This article appears in the Winter 2024 issue
On August 29, 1786, 1,500 disgruntled farmers, burdened by oppressive taxation and debt collection by the State of Massachusetts, assembled. Marching in military formation to the sound of fifes and drums, they surrounded the Hampshire County courthouse to prevent the Court of Common Pleas from conducting foreclosure and property seizure hearings. A tense but peaceful standoff ensued.
Woodcut illustration depicting Daniel Shays (left) and fellow Regulator Job Shattuck from Bickerstaff’s Boston Almanac, 1787. Image Credit: National Portrait Gallery
The county judges, convened in a nearby tavern, agreed to postponed hearings and adjourned. This incident marked the onset of Shays’s Rebellion, a regional uprising (named for Daniel Shays) strongly rooted in the Connecticut River valley that influenced the nation’s early history.
A combination of economic, regional, and political factors incited the rebellion. When the American Revolution ended, the new nation faced a financial crisis triggered by war debt and a British trade embargo on American goods. Merchants began to demand immediate payments with hard coin instead of extending credit or the long-standing custom of bartering with produce or seasonal labor. Farmers were particularly impacted, many of whom were Revolutionary War veterans who had risked their lives for minimal compensation during the war. Now they faced property seizures and incarceration if they couldn’t make prompt payments for overdue debts and taxes.
Regional tensions exacerbated dissent in Massachusetts, where the first state constitution, enacted in 1780, enhanced the power of wealthy Bostonians and merchant towns in the eastern part of the state. The crisis deepened in 1785 when Governor John Hancock, whose lenient tax policies gained him considerable popularity with the general public, withdrew from that year’s election. His successor, James Bowdoin, who attained office partly through intervention of wealthy state senators, steeply raised taxes and demanded immediate payments of back taxes to pay off the state’s war debt. Many residents suddenly faced an economic burden considerably worse than under British rule.
“Shays Insurrection,” a portrayal of Daniel Shays’s army fleeing Springfield after attempting to occupy the federal arsenal in January 1787. From Edward Ellis, History of Our Country, 1900.
Pressure had been mounting for some time as conditions deteriorated in rural communities. Connecticut Valley farmers clamored for reforms during conventions in Hadley, Hatfield, and Deerfield. Foreshadowing what was coming, an angry mob, incited by activist minister Samuel Ely, stormed the Northampton courthouse in April 1782.
Among the many farmers who had been summoned to debtor’s court was Daniel Shays, a Revolutionary War veteran who served with distinction at Bunker Hill, Saratoga, and other conflicts. After the war, Shays established a farm in Pelham, Massachusetts, where he commanded the local militia. Though the uprising would be named for him after Massachusetts authorities vilified him as its leader, Shays was just one of many leaders.
Nearly half of the rebellion participants came from Hampshire County, which at the time encompassed the entire Connecticut River valley and adjacent hill towns in western Massachusetts. Towns with influential families and leaders, such as Pelham, Amherst, and Colrain, became hotbeds of activity; other communities remained neutral. Though sources often broadly characterize the insurgents as indigent farmers (one of several longstanding misconceptions cited by historians Leonard Richards and Daniel Bullen), many were decorated war veterans, members of prominent families, and/or elected officials.
The farmers initially attempted to attain reforms through petitions to the state government (hence the term Regulators, which came from a similar regional uprising against taxation in North Carolina that happened before the war), but when the Massachusetts General Court adjourned in July 1786 without passing relief measures, they shifted to forcible actions. During emergency meetings at taverns and inns, town leaders coordinated plans to close state courthouses, starting with the aforementioned protest in Northampton.
After their success in Northampton, Regulators shut down courthouses in Worcester, Great Barrington, Taunton, and Concord. In late September, 2,000 men under the command of Shays disrupted hearings at the Springfield Supreme Judicial Court. To the chagrin of local officials and merchants, state militiamen led by General William Shepard of Westfield, who had fought alongside Shays and other Regulators during the Revolution, declined to disperse the rebels. Additional court closures followed in December 1786 in Worcester and Springfield.
Shays’s Rebellion Monument in Petersham, MA, marks the day (February 4, 1787) that Daniel Shays and 150 Regulators were routed by Massachusetts forces. Erected by the New England Society in 1927, it asserts that “This victory for the forces of government influenced the Philadelphia Convention which three months later met and formed the Constitution of the United States” and “Obedience to Law Is True Liberty.” Image Credit: John Burk
News of the rebellion soon resonated with national leaders. The uprising deeply troubled George Washington, who viewed anarchy as a threat to the nation he had helped establish. (Under the nation’s original Articles of Confederation, Congress lacked power to raise armies, collect taxes, and address issues within states.) In a letter to James Madison, Thomas Jefferson took a more favorable view. “A little rebellion is a good thing. It is a medicine necessary for the sound health of government,” he wrote.
To restore order, in January 1787 Governor Bowdoin commissioned a private army of 3,000 men, funded by wealthy merchants and commanded by General Benjamin Lincoln. Faced with the new threat, the Regulators attempted to seize the federal arsenal at Springfield, which housed an array of weapons and ammunition. Anticipating their actions, Gen. Shepard assembled 900 state militiamen to guard the facility.
When Lincoln’s army reached Worcester, the Regulators advanced on Springfield from three directions. Shays led 1,200 men to Palmer, while 400 Connecticut Valley Regulators assembled with Eli Parsons in Chicopee. Across the Connecticut River in West Springfield, Luke Day commanded 600 Regulators from the western hill towns and Connecticut. To isolate and disrupt communication between Shepard and Lincoln’s state forces, the Regulators guarded roads, bridges, and the Connecticut River ferry. However, plans for a coordinated attack went awry when Shepard’s soldiers intercepted messages from Day to Shays and Parsons.
Shortly before sunset on January 25, Shays’s men began their fateful advance on the Springfield arsenal. After warning shots failed to deter them, Shepard’s troops fired grapeshot (small iron balls), killing four Regulators and wounding twenty. Cries of “Murder! Murder!” resonated across the green. Confronted with the sudden reality of armed resistance and death, Shays’s Regulators fled to Ludlow, just east of Chicopee, and attempted to regroup.
On January 27, Lincoln’s army reached Springfield. Shepard’s soldiers isolated Day’s group on the west side of the Connecticut River. Their forces outnumbered and divided, Shays and Parsons retreated north to Pelham. When they passed through South Hadley, government supporters shot two Regulators at a tavern. According to an unsubstantiated legend, some rebels sheltered with their horses on a ledge on Mount Norwottuck in the Holyoke Range. Today the site, known as the Horse Caves, is a popular landmark of the New England National Scenic Trail.
Lincoln and Shepard’s forces pursued Day’s men along the west side of the valley to Northampton. After Regulators captured sixty of Shepard’s soldiers in Southampton, militiamen tracked them down in Middlefield.
Day crossed the Connecticut River and joined Shays and Parsons at Pelham. Lincoln’s army encamped in Hadley during an outbreak of frigid cold that temporarily halted actions by both sides.
On February 3, Shays and approximately 1,000 Regulators relocated twenty miles further northeast to the isolated town of Petersham. Lincoln and his soldiers followed at night via a circuitous route through Shutesbury and New Salem to avoid detection. After a severe winter storm blew in, Lincoln’s weary, frostbitten troops pressed on through deep snow and high winds, reaching Petersham on the morning of February 4.
Caught off guard, the Regulators hastily dispersed when Lincoln’s men approached their camp. Lincoln claimed 150 captives; all were sent home on parole. Shays fled north with 300 followers to Vermont, which at the time was an independent republic that offered a refuge from extradition to Massachusetts. After crossing the Connecticut River at Putney to avoid pro-government merchants in Brattleboro, the rebels sheltered with sympathetic families near Arlington, Vermont.
Monument to General William Shepard, Westfield, MA. Shepherd fought alongside Shays and other Regulators during the Revolution. Early in Shays’s Rebellion he refused to disperse the rebels, but later led the state’s defense of the Springfield arsenal. Image Credit: Wikimedia
The uprising gradually subsided in early 1787. Appeals by Shays and his officers to Vermont’s leaders and the royal governor of Quebec elicited sympathies but no aid. The last significant conflict occurred on February 27 at Sheffield in southern Berkshire County, where a clash between Regulators and state militiamen resulted in five deaths and thirty injuries. Roughly 4,000 insurgents received pardons after they signed confessions, pledged allegiance to the state, and surrendered their firearms. Eighteen men received death sentences, but only two executions were carried out, likely due to fears of reprisals against the state.
Although the rebellion ended with defeat for the Regulators, its repercussions extended across the nation. Reforms quickly followed in Massachusetts after disgruntled voters replaced Bowdoin by reelecting Hancock as Governor by a landslide in April 1787. Hancock’s administration reduced taxes, placed a moratorium on debts, released imprisoned debtors, and rescinded bounties on Shays, Day, and Parsons.
By providing shelter to Shays and the Regulators, Vermont helped expedite its establishment as the nation’s fourteenth state. Concerned that the territory, originally part of New York, was becoming a haven for outlaws and subversive activities, Alexander Hamilton drafted a bill that supported statehood in March 1787.
Shays remained in Vermont until 1795, when he relocated to upstate New York. Although he died in poverty and relative obscurity in 1825 at the age of seventy-eight, his name subsequently gained iconic status. In an ironic twist, Shays’s former Pelham farmstead now lies beneath the waters of Quabbin Reservoir, a controversial project in which 3,500 Swift River valley residents were dislocated to create a water supply for the greater Boston area in the 1930s.
On a national scale, the rebellion influenced discussions and debates related to the development of the United States Constitution. For leaders such as Washington, Hamilton, and Madison, the uprising underscored weaknesses of the Articles of Confederation and the need for a strong federal government. Nationalist supporters frequently cited Shays and the rebellion when lobbying for reforms.
Motivated by the events in Massachusetts, Washington came out of retirement to serve as presiding officer at the Philadelphia Constitutional Convention in May 1787 before becoming the nation’s first president two years later. Despite considerable opposition from backcountry towns, ratification of the Constitution passed by a narrow margin in Massachusetts in January 1788. During an address in 1802, statesman John Quincy Adams proclaimed that “the insurrections of the year 1786 form one of the most instructive periods in the history of our country.”
John Burk is a writer, photographer, and historian from western Massachusetts whose credits include books, guides, and articles in nature and regional publications. His regular column, Central Watershed Outings, does not appear in this issue.