At Woodlands, Simms awaited the coming of the war which he had predicted for a number of years. There he was when the battle of Fredericksburg filled him with triumphant joy, and he saw in fancy "Peace with her beautiful rainbow plucked from the bosom of the storm and spread from east to west, from north to south, over all the sunny plains and snowy heights." Unfortunately, his radiant fancy wrought in baseless visions and the fires of the storm had burned away that brilliant rainbow before Peace came, as a mourning dove with shadowy wings hovering over a Nation's grave.

In May, 1864, Simms went to Columbia and was there when the town was destroyed by fire, the house in which he was staying being saved by his presence therein. "You belong to the whole Union," said an officer, placing a guard around the dwelling to protect the sturdy writer who counted his friends all over the Nation. He said to friends who sympathized with him over his losses, "Talk not to me about my losses when the State is lost."

Simms describes the streets of Columbia as "wide and greatly protected by umbrageous trees set in regular order, which during the vernal season confer upon the city one of its most beautiful features."

The Daily South Carolinian was sent to Charleston to save it from destruction. Its editors, Julian Selby and Henry Timrod, remained in the office on the south side of Washington Street near Main, where they prepared and sent out a daily bulletin while bomb-shells fell around them, until their labors were ended by the burning of the building.

From the ashes of the Carolinian arose the Phoenix and Simms was its editor through its somewhat brief existence. Selby relates that Simms offended General Hartwell and was summoned to trial at the General's headquarters on the corner of Bull and Gervais Streets. The result of the trial was an invitation for the defendant to a sumptuous luncheon and a ride home in the General's carriage accompanied by a basket of champagne and other good things. The next day the General told a friend that if Mr. Simms was a specimen of a South Carolina gentleman he would not again enter into a tilt with one. "He outtalked me, out-drank me, and very clearly and politely showed me that I lacked proper respect for the aged."

The Phoenix promptly sank back into its ashes and Simms returned to Charleston to a life of toil and struggle, not only for his own livelihood but to help others bear the burden of existence that was very heavy in Charleston immediately succeeding the war. Timrod wrote to him, "Somehow or other, you always magnetize me on to a little strength."

In 1866 Simms visited Paul Hayne at Copse Hill, the shrine to which many footsteps were turned in the days when the poet and his little family made life beautiful on that pine-clad summit. Hayne welcomed his guest with joy and with sorrow—joy to behold again the face of his old friend; sorrow to see it lined with the pain and losses of the years.

Of all their old circle, Simms was the one whose wreck was the most disastrous. He had possessed so many of the things which make life desirable that his loss had left him as the storm leaves the ruined ship which, in the days of its magnificence, had ridden the waves with the greatest pride. The fortnight in Copse Hill was the first relief from toil that had come to him since death and fire and defeat had done their worst upon him. His biographer says, "He was as eager as ever to pass the night in profitless, though pleasant, discussions when he should have been trying to regain his strength through sleep." To a later visitor Paul Hayne showed a cherished pine log on which were inscribed the names of Simms and Timrod.

Upon the return of Simms he wrote to his friend at Copse Hill that no language could describe the suffering of Charleston. He said that the picture of Irving, given him by Hayne, served a useful purpose in helping to cover the bomb-shell holes still in his walls. "For the last three years," he writes, "I have written till two in the morning. Does not this look like suicide?" He mentions the fact that he shares with his two sons his room in which he sleeps, works, writes and studies, and is "cabin'd, cribbed, confined"—"I who have had such ample range before, with a dozen rooms and a house range for walking, in bad weather, of 134 feet." The old days were very fair as seen through the heavy clouds that had gathered around the Master of Woodlands.

In 1870, June 11th, the bell of Saint Michael's tolled the message that Charleston's most distinguished son had passed away. His funeral was in Saint Paul's. He was buried in Magnolia Cemetery, at the dedication of which twenty-one years earlier he had read the dedication poem. The stone above him bears simply the name, "Simms."