June 15, 1886: The Clemens family and governess Rosa Hay (a party of six) left Hartford for Elmira and spent the night at the [Sam to Orion June 2] Gedney House at 40th Street and Broadway in New York
June 21, 1886: The Clemens family and governess Rosa Hay left Elmira and traveled by rail to Rochester. They had returned to Elmira by July 10th.
July 30, 1886: New York
August 1 Sunday – In Lawrence, New York (Long Island)
August 2 Monday – In New York City, about to leave for Philadelphia,
August 4, 1886: Hartford
August 5, 1886: Returns to Elmira
September 17, 1886: Family departs Elmira for New York, and return to Hartford.
September 27, 1886: Clemens family back in Hartford.
The family left Hartford for New York on June 15, overnighted at the Gedney House in the theater district on Broadway, and arrived in Elmira the next day. On June 21 they departed Elmira and paused in Niagara Falls, registering at the Cataract House, where Sam, Livy, and her parents had sojourned in late July and early August 1869. Rather than journey by train, Sam preferred to travel as much as possible by boat. They embarked from Buffalo on the Great Lakes steamer India on June 22, landing six days later in Duluth, where they registered at the St. Louis Hotel. Susy noted in her diary on June 26 that the family was en route “to Keokuk to see Grandma Clemens, who is very feeble and wants to see us, and pertickularly Jean who is her namesake. We are going by way of the lakes, as papa thought that would be the most comfortable way.” They arrived on June 29 in Minneapolis, where they took rooms at the Ryan Hotel. The Minneapolis Tribune remarked on Sam's appearance in the hotel lobby: “a quiet man of medium height, attired in alligator slippers, a light gray suit, and a pearl colored high hat. In his mouth he had the stem of a corn cob pipe. After an excursion to Minnehaha Falls, the family railed to St. Paul and boarded the steamboat War Eagle for Keokuk, arriving on July 2, He repeated to a reporter his claim that this part of the river was much more charming than the Mississippi below St. Louis: “One finds all that the Hudson affords—bluffs and wooded highlands—and a great deal in addition. Between St. Paul and the mouth of the Illinois River there are over 400 islands, strung out in every possible shape. A river without islands is like a woman without hair. She may be good and pure, but one doesn't fall in love with her very often.” Outfitted in a white duck suit, Sam delivered a Fourth of July oration at Rand Park on July 3—the Fourth was a Sunday—and, according to the St. Louis Globe-Democrat, “delighted a vast concourse of people by his happy and pointed remarks.” The Clemenses lingered in Iowa until July 7, enduring “four or five days & nights of hell-sweltering weather.” Sam saw “my aged mother in life" for the last time on this trip. “Her memory was decaying; indeed, for matters of the moment it was about gone; but her memories of the distant past remained and she was living mainly in that far away bygone time.” To flee the heat they railed to Chicago, where they registered at the Richelieu Hotel. Livy fell ill, so Sam entertained his daughters, accompanying them to a Battle of Shiloh panorama the afternoon of July 8. That evening Sam and the children walked a block north of their hotel on Michigan Avenue to the Exposition Building to hear the Chicago Symphony Orchestra but they arrived late and, after listening outside the hall to part of Beethoven's Symphony Number 5 in C Minor, they returned to the hotel.
Back in Elmira on July 10, Sam spent the balance of the summer at leisure, though he read from his writings for the inmates of the Elmira Reformatory on July 21; vacationed from his summer vacation for a few days at Long Beach, New York; and attended the trial of department store magnate John Wanamaker, against whom Webster and Company had brought suit for marketing Grant's autobiography at a discount, in Philadelphia in early August. He wrote Franklin Whitmore from Elmira on September 16 that the family had enjoyed “an unimaginably delightful summer” and told a reporter the next day that he was “not at work; not doing a single thing; just loafing; that's all. I made up my mind that I would loaf all summer, and I intended to do it.” The same day Sam sat for this interview, the family left Quarry Farm for New York, where they stayed a week at the Murray Hill Hotel near Grand Central Station on Forty-Second Street. They detoured for a day to Spring Lake Beach, New Jersey, and returned to Hartford on September 27.”
[From page 511-2 The Life of Mark Twain - The Middle Years 1871-1891]