Caleb Haskell Begins Arnold’s Expedition to Quebec

Revolutionary War soldier Caleb Haskell must have thought Arnold’s expedition to Quebec was a good idea. He signed up for it during the Siege of Boston. Benedict Arnold had persuaded George Washington that the British would use Quebec to launch military operations. Arnold had traded in the region and believed Quebec was lightly defended.

Detail of 1795 map overlaid with Arnold's expedition route. A Cambridge; B Newburyport; C Fort Western; D Fort Halifax; E Great Carrying Place; F Height of Land; G Lake Megantic. Courtesy Boston Public Library.

Detail of 1795 map overlaid with Arnold’s expedition route. A Cambridge; B Newburyport; C Fort Western; D Fort Halifax; E Great Carrying Place; F Height of Land; G Lake Megantic. Courtesy Boston Public Library.

In the fall of 1775, Benedict Arnold led a force of 1,100 Continental troops from Cambridge, Mass., to Quebec City. Richard Montgomery led another expedition to invade Quebec from Lake Champlain.

It didn’t go well. Arnold’s men traveled 350 miles – twice as far as they planned — through poorly charted wilderness in what is now Maine. The men endured grueling portages up the Kennebec River. The boats leaked, ruining precious gunpowder and food supplies. By the time Arnold reached the French settlements above the St. Lawrence River, he had only 600 starving men. The siege of Quebec failed.

Caleb Haskell Signs Up

On May 5, 1775, Caleb Haskell enlisted as a soldier in the American Army in Newburyport, Mass. From that day through May 30, 1776, he kept a diary.

He described marching to Cambridge, where his unit under Capt. Ezra Lunt participated in the Siege of Boston. There was guard duty, Sunday worship, parading on the common, skirmishing with the enemy, seizing cattle and cannon. He made it through the Battle of Bunker Hill unscathed.

Caleb Haskell signed up for Arnold’s expedition to Quebec on Sept. 11. He marched to Newburyport and, a week later, boarded one of the 11 transport ships bound for Canada.

On Tuesday, Sept. 19, he recorded in his diary the troops’ departure:

This day about 9 o’clock weighed our anchors, and came to sail with a southwardly wind. After we got over the bar, we lay to, waiting for orders from the Commodore. At 10 o’clock received orders.

First signal.–Signal for speaking with the whole fleet: Ensign at main-topmast head.

Second signal.–Signal for chasing a sail: Ensign at fore-topmast head.

Third signal.–Signal for heaving to in the night: Lantern at mast-head, and two lights if head on shore, and three guns if head off shore.

Fourth signal.–For making sail in the night. Lantern at mast-head and four guns; and jack at fore-topmast head in the day.

Fifth signal.–For dispersing, and every vessel making the nearest harbor: Ensign at main-peak.

Sixth signal.–For boarding any vessel: Jack at main-topmas head and the fleet to draw up in line as near as possible.

N.B. No small arms to be fired at three o’clock.

The jack was hoisted on board the Commodore. We made sail with a fine breeze; in the evening, the wind blew quick at S.E. About 1 o’clock we hove to and lay until morning.

Arnold’s route through northern Maine is listed on the National Register of Historic Places as the Arnold Trail to Quebec.



  1. Dave Sullivan

    September 19, 2014 at 10:38 am

    My 6th Great Grandfather Captain James Howard commanded Fort Western and was also a friend of Arnold’s (until he turned on the Colonialists). After the war, the Fort was decommissioned and Captain Howard (now also the Judge of this Maine Province of the Commonwealth of Massachusetts) purchased the property and over an additional 500 acres. Then two of his sons (William & Samuel) converted the Fort into a large family home and store (post office/bank/swap shop). This new settlement eventually became Maine’s capital Augusta. Old Fort Western still exists today, and is the oldest wooden fort in the US, as a wonderful museum – where time has stood still. It’s a MUST SEE, for history buffs!

  2. Bill Carlson

    September 19, 2014 at 2:17 pm

    Sitting in Newburyport right now on the river.

  3. Daniel C. Purdy

    September 19, 2014 at 9:13 pm

    Oh, what is Kenneth Roberts wonderful book about this catastrophe?

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  9. Les Haskell

    November 21, 2016 at 1:04 am

    Caleb was my great grandfather’s great grandfather.

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