The Battle of Deering Oaks

The Battle of Deering’s Oaks
by Herbert G. Jones
excerpted from the book “Maine Memories”
published in 1940 by Harmon Publishing, Portland, Maine

Photographs of Deering Oaks circa 1900-1910

Tinting and colorization done by MaineUSA Graphics and Web Design. Copyright © 2013

Deering Oaks, Portland, Maine USA

Deering Oaks Park

“Portland— the beautiful” is the happy phrase so often used by the tens of thousands of outsiders who visit and re-visit us year after year. And interesting too, is the reaction of world-travelers who, surfeited with old world glories, tell is that nature itself was more than lavish when she fashioned our beautiful city. In contrast to the artificialities of the foreign scene they find in our environment, a calm, unharrassed nature-created atmosphere that is quite refreshing. They marvel at the gorgeousness of our summer view from the Western Promenade with its magnificent panoramic background of the White Mountains; the picturesque charm of Cape Elizabeth that is entirely its own with its tapestry of fir-clad woodlands and the whitened steeples of century old churches; and from the Eastern Promenade the splendid sweep of the isle-studded bay from the historic headlight to the mouth of the Kennebec. Ah! perhaps you think I’m getting too enthusiastic! Well, as far back as 1790, a French nobleman, the Duc de la Rochefoucauld was singing its praises. He was surprised to find in this neck of the woods such an attractive, decent, well kept town. “This town of Portland,” he said, “may be reckoned as really handsome.”

Thurston Peck, a famous critic and world traveler, writes this testimony. “Portland, of all the places on this habitable earth is where one can get the keenest sense of what is good in life. The sunny fields of Kent are very fine. The roses of the Riviera, and the blue of the Italian lakes are charming. The palms of Santa Catalina sway with seductive fascination, yet these may all go hand when I recall the buoyancy of soul which came over me when I made my visit to Portland.”

Deering Oaks, Portland, Maine USA

Deering Oaks Park

Now ’tis true, that Old Parson Smith of the First parish Church was not unduly impressed on his first visit to our little town in the early 1700’s. He referred to its inhabitants “as rather mean animals.” But then he was just out of Harvard. Nevertheless, even he succumbed to the inevitable lure for he spent the rest of his long life here and became one of Portland’s first important citizens. And Portland was exceedingly fortunate in the character of its early citizens for no town had a people better fitted to lay its early foundations. They were a hardy lot, frugal and industrious, patriotic and generous.

An excellent example was the Deering family headed by Nathaniel Deering who came here from Kittery inDeering Oaks 1761. Distinguished not only as merchants, but in various walks of life, they were among the greatest benefactors this city ever had. They donated more than 95 acres of land and much money for the building of its early homes and streets. Their generosity was climaxed in the deeding of the lovely Deering oaks to the city as a public park for the enjoyment of all, and thus saved it from the ignominious fate of becoming a railroad freight yard.

It must seem unbelievable to us today that this peaceful sylvan spot in the heart of the city once resounded with the terrifying war whoops of Indian braves and the clash of arms; the heavy trudge of oxen hauling heavy red pungs from the Coos country laden with hogs, butter and cheese; the busy hum of industry and shipbuilding; horseracing, and the raucous ballyhoos of circus touts and midways. Doubtless many of those magnificent oak trees, under which you take your grateful shade, must have looked down upon that historic early morning scene 250 years ago, when the memorable Battle of Deering Oaks was fought between the volunteer soldiers of Col. Benjamin Church and a large force of hostile redskins led by the French. (The word redskins is left in as it is in the original… that description would not be acceptable today.) Considering the numbers engaged it was one of the most important battles ever to take place on Maine soil for according to historians, the fate of Maine hung in the balance, whether it was to become a part of French Canada or remain in the United States.

Deering Oaks, Portland, Maine USABut of course it was not known as Deering Oaks in those days as it was all a part of the ancient farm of Anthony Brackett which extended for many acres. And we must visualize a far different Portland or Falmouth as it was then called. And we must visualize a far different Portland or Falmouth as it was then called. It was a very small village consisting of about 25 families living mostly in wooden one-storied houses, clustered for protection around Fort Loyal which stood on the site of the present Grand Trunk Station. There was an ancient ferry at the foot of Hancock street and it was there the adventurous traveler embarked on his perilous journey which took him to Spurwink, Black Point, and the scattered settlements further on. Opposite the town landing was the village store kept by Captain Sylvanus Davis, an officer at the fort, and nearby was the inevitable town-tavern, owned by Richard Seacombe. West of Center Street was the primeval forest home of all kinds of wild animals, deer, moose, bear, and the fierce Indian devil, the panther.

During the summer of the fateful year of 1689, a threatening band of hostile Indians had gathered on Peaks Island, then known as Palmers Island, and the inhabitants of the town had sent frantic appeals to Boston for more soldiers as they were ill-prepared to meet any attack. On the eve before the battle Col. Benjamin Church, a skillful fighter in the earlier Indian wars, and a force of about 160 men, including some friendly Indians, landed at the ferry and were concealed i the fort and nearby houses. Early on the morning of September 28th they were quietly marched to the thick forest growths which is now Deering Oaks. In the meantime, however, the Indians had not been idle. During the dark hours of the night, their forces increased to 700 warriors, they paddled their canoes across Back Cove and landed near the Kennebec Street entrance to the park. They then advanced up the short rise and camped in Anthony Brackett’s orchard, near the present Deering mansion. there they were discovered by one of Brackett’s sons making a hasty breakfast of fish brought from the island. It was here action commenced which lasted six hours. The whites, adopting the cunning tricks of the redmen, fought in frontier fashion, matching their stealth in taking advantage of every bit of cover.

Deering Oaks, Portland, Maine USA

Deering Oaks Park

After an hour of desultory firing, Col. Church decided to attack the enemy in the rear, and taking two of his companies proceeded up the creek which was then a part of the Back Cove waters and covered a large section of the Oaks. The Indians perceived his object, however, and retreated in the direction of what is now Deering Avenue. The Colonel, supposing they sought some other way to attack the town, rushed his small force there, but found no trace of them. He went as far as Clark’s field on Munjoy Hill but finding the cattle peacefully grazing, a sure sign that no enemy were in that vicinity, he cautiously retraced his steps through the thick woods and underbrush and rejoined his two other companies under the command of Captain Hall, who had borne the brunt of the battle so far. He found these soldiers in a critical condition as most of the bullets supplied them were too large for their muskets. Word was sent back to the people in the town to hammer all ammunition into slugs so it could be utilized.

Credit for saving the battle and the lives of the villagers from massacre is given to a loyal Indian named Captain Lightfoot, who at the risk of his life, waded the creek again and again, carrying gunpowder on his head and a kettle of slugs in each hand— another example in Maine history of Indian loyalty to his white neighbor in times of stress. This heroic act on the part of the Indian so heartened the soldiers that they made a determined advance against great odds and kept up such a hot accurate fire that the enemy ultimately fled in disorder carrying their dead with them, as was their custom. The defeat of the natives was so decisive that the town of Falmouth was free from Indian troubles for more than a year. The soldiers lost 14 killed and 7 wounded. Anthony Brackett, owner of the farm, was shot defending his home. Some years before, he and his wife had been captured by the Indians and taken to the Indian encampment at Mere Point near Brunswick. They made a miraculous escape due to the resourcefulness of the wife. She had found an abandoned canoe which she mended with a needle and thread and in this frail makeshift they made their way to safety. George Bramhall, another large land owner and from whom the Bramhall section was named, was mortally wounded and died the next day. Of great service to Col. Church was a fighting parson, the celebrated Rev. George Burroughs, who preached in the village church and who some years later was put to death by the Puritans for witchcraft on the false testimony of a 12 year old girl.

It seems but a short span of time since the days when this delightful woodland which we know as the oaks was the scene of a busy ship wharf, and a tide mill which ground corn and salt for its owner James Deering. This was the same James Deering who build the old Deering Mansion in 1804. The very spot now occupied by the cities tennis courts once saw a successful ship launching, for the waters of back Cove flowed through the Oaks, making a busy ship thoroughfare to the open sea. Old Deering bridge built in 1906, then connected Portland with the nearby village of Woodfords and under its span the small boys of Longfellow’s time used to go smelt fishing, and dig for clams. And of course they never forgot to visit the apple orchard on the Deering farm. During the 1870’s, the great winter sport was horse racing, which usually took place on Saturday afternoons on Portland Street with the finish at the present entrance of the Oaks. The park then was rather a forbidding and lonesome place at night, entirely without lights, with mere footpaths through the dense growth of trees, and rude plankings fording the gullies and small creeks. Opposite the Oaks, towards the city, was nothing but open fields stretching from Deering Avenue to High Street and from Portland Street to Cumberland Avenue. Here the old time circuses of Van Amberg and Turner Brothers pitched their tents presenting a colorful scene with flaring kerosene lamps and gaily decorated wagons and costumes.

And now left to us as a graceful link with the past, is the old Deering mansion itself. It is a perfect example of a Maine farm manor house with its beautiful frontage, serene and practically untouched in its pristine state, both in its interior as well as exterior, deeply reminiscent of the early days of great hospitality. A fitting example of a true Portland home.

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