Before dawn on October 22, 1776, roughly 750 Continental soldiers crept toward a Loyalist camp on a hill in Mamaroneck. The camp belonged to Lt. Col. Robert Rogers's Queen's Rangers. They had marched into town the day before and settled on Heathcote Hill. The Battle of White Plains, on October 28, was six days away. The Americans got past the perimeter guards. Then Rogers rallied his camp. Col. John Haslet chose not to press an attack into a dark, now-alert encampment and pulled his men back, taking prisoners, arms and colors with him.
Two hundred fifty years later, Mamaroneck is honoring that night with a free afternoon at Harbor Island Park on Sunday, Oct. 18. A narrated reenactment of the Skirmish at Heathcote Hill is scheduled for 3 p.m. Harbor Island is the right place for a crowd. The skirmish itself happened up the hill, at a corner where a state marker stands in front of a church on Fenimore Road. The anniversary date, Thursday, Oct. 22, falls between two weekends of programming and has nothing scheduled. Getting the most out of the 250th means visiting both places.
What the marker on Fenimore Road says, and where the record is more complicated
The New York State marker for the "Skirmish of Heathcote Hill" is at Fenimore Road and Cortlandt Avenue, in front of St. John's Lutheran Church. The inscription reads:
"Gen. Washington sent 750 men to attack 400 Queen's Rangers encamped here in the pre-dawn Oct. 22, 1776."
That's one sentence of cast metal. Longer accounts add detail, and in places they disagree. Journal of the American Revolution's account of the Battle of Mamaroneck says Lord Stirling ordered the operation, with Col. John Haslet and Maj. John Green leading in the field. The force was mostly Delaware and Maryland Continentals, plus Virginia Continentals and local guides. The marker names Washington as the man who sent them, and the Journal's account names Stirling as the one who gave the order.
The prisoner count varies too. Haslet's own account, as quoted by the Journal of the American Revolution, puts it at 36. The Westchester County Historical Society timeline says 31. That same timeline records that the Rangers drove the Americans off but took heavier casualties. So by one measure the Loyalists won, and by another the raiders did, which is probably why the event is usually called a skirmish rather than a battle.
The Westchester County Historical Society's 250th anniversary History Hunt includes the spot as "Skirmish at Heathcote Hill," listed at 132 Fenimore Road. A marker database gives a nearby Cortlandt Avenue address instead. Both point to the same intersection.
Why the reenactment is at the harbor
The Mamaroneck Historical Society's list of historic sites places the skirmish near Fenimore Road and Cortland Avenue. The Society's history of local streets describes the Boston Post Road as the village's original development spine, the road the armies of 1776 would have known. A residential corner with a church on it has no room for regiments, fifes and a crowd. Pavilion Field at Harbor Island Park does, and it has free parking.
No building at the reenactment site dates to the skirmish. The Historical Society's list of local sites dates the 1816 Schoolhouse in Harbor Island Park to 1816, forty years after the raid. The DeLancey House at 410 W. Boston Post Road is dated 1792 and no longer stands on its original site. In Mamaroneck, the plaque on Fenimore Road is the only physical marker of the skirmish.
Sunday, Oct. 18, at Pavilion Field
The Revolution on the Sound program from Revolutionary Westchester 250 describes Mamaroneck 250 as a free waterfront family afternoon from 1 to 5 p.m. It includes kids' activities billed as "Join the Continental Army," heritage craft demonstrations, and period games run by staff from Philipse Manor Hall State Historic Site. The 1st Delaware Regiment, a reenactor unit known as the Delaware Blues, will be there all day. That's a fitting choice, since Delaware troops made up much of Haslet's raiding force.
| Time | Program |
|---|---|
| 1:00 p.m. | Live music, opening remarks, recognition of the Skirmish at Heathcote Hill |
| 1:15 p.m. | Storytelling by Jonathan Kruk |
| 1:30 p.m. | The Ward family and British General Howe, a family split between Patriot and Loyalist sides |
| 2:00 p.m. | "Life as a Hudson Valley Soldier" with Robert Buccheri, with uniforms to try on and Manual of Arms drills |
| 3:00 p.m. | Narrated reenactment of the Skirmish at Heathcote Hill, 1st Delaware Regiment and visiting regiments |
| 3:45 p.m. | "The Revolution in Song and Story" with Linda Russell |
| 4:00 p.m. | Meet Deborah Sampson |
| 4:45 p.m. | Fife and drum performance and parade by Ministers of Apollo |
The Ward family segment reflects how divided 1776 was locally. Its subject is a family split along Patriot and Loyalist lines, which is a good frame for a raid on a Loyalist regiment camped among local homes. Kruk's storytelling covers the armed whaleboats that worked Long Island Sound during the war.
The same morning, the regional program puts on a reenactment of the Battle of Pell's Point/Pelham at Orchard Beach in the Bronx from 10 a.m. to noon. With the Mamaroneck program starting at 1 p.m., anyone up for a doubleheader can catch both.
Thursday, Oct. 22, at the corner where it happened
The Historical Society, Town and Village calendars list nothing for the actual anniversary. Thursday, Oct. 22, is exactly 250 years after the dawn raid. The marker at Fenimore Road and Cortlandt Avenue will be standing there as usual, and the timing is precise. The Rangers arrived on October 21 and the attack came before dawn the next morning. A visit before school drop-off or the morning train would put someone at the site at roughly the hour the guards were surprised.
The plaque gives 750 attackers and 400 Rangers, the same engagement the Delaware Blues will reenact on Pavilion Field four days earlier.
The weekend after: Saturday, Oct. 24, and Sunday, Oct. 25
The commemoration picks up again two days later, and the schedule moves between Larchmont, the library and the harbor.
- 10 a.m., Saturday, Oct. 24. The Town of Mamaroneck holds its America 250 Ceremony at Memorial Park & Tennis Courts on Myrtle Boulevard in Larchmont.
- 1 to 2 p.m., Saturday, Oct. 24. Jonathan Kruk returns with "Tales of Revolutionary Westchester" at Mamaroneck Public Library, 136 Prospect Avenue, in a program listed by the Mamaroneck Historical Society.
- 6 to 9 p.m., Saturday, Oct. 24. The Village's Harbor Island Pavilion Haunted House opens at the Stephen E. Johnston Beach Pavilion in Harbor Island Park. The Village describes it as a walkthrough of about 15 minutes, best suited to teens and adults, with no tickets required.
- 11 a.m., Sunday, Oct. 25. The Spooktacular Halloween Parade steps off from The Regatta at 123 Mamaroneck Avenue. Activities follow on Pavilion Field from 11:45 a.m. to 2 p.m. The Chamber of Commerce calendar lists noon to 3 p.m. The Village's own September 10 announcement and its detailed schedule support the earlier window.
Pavilion Field hosts the 250th reenactment one Sunday and the Halloween parade activities the next. The parade starts on Mamaroneck Avenue, which passes two of the summer's new openings.
Two newer stops on Mamaroneck Avenue
The Journal News reported that The Cloudy Bean, a specialty coffee café at 325 Mamaroneck Avenue, opened Aug. 31, 2026. Westchester Magazine covered its soft opening in early September. It's an easy coffee stop after a morning visit to the Fenimore Road marker on the 22nd, or before the parade lines up at The Regatta on the 25th.
Farther up the avenue at 414, the Italian sandwich shop Apposto opened July 21, 2026, according to the same Journal News roundup. Food trucks aren't part of the Mamaroneck 250 listing, so picking up sandwiches here before Sunday's 1 p.m. opening means you can spend the whole afternoon on the field.
Kamala Vittal follows details like these closely, from where a 1776 marker stands to the week a new café opens, because she believes knowing a town's history is part of feeling at home in it. If you're new to Westchester, or deciding where to live, Kamala Vittal would be happy to walk you through what makes each one distinct. Let's Connect.
