John moved from Brightwood, Madison County to Roanoke,Virginia as did his brothers J Edgar and Jim.

In 1897, he had moved to Chicago, Illinois, only to return to Roanoke to wed Mary Allen Fuqua, daughter of Robert M and Nannie Giles Fuqua of Vinton, Virginia on October 27, 1897. Bridesmaid were Eliza Fuqua, Fannie Wayland (John's sister), and Ida Black. Groomsmen were S. F. Fuqua, R. S. Thomas, and T. W. Hawkins. The couple, accompanied by Miss Fannie Wayland and J Edgar Wayland (John's brother), left on the 10:50 pm train to visit with John's parents who were living in Madison. Afterward John and Mary traveled to Chicago to reside.

By 1900, John and cousin, Marvin (New Franklin, Missouri) lived with his brother, Jim, and all three worked for the Railroad. He was employed as their electrician.

John and Mary had two children, Nannie Elizabeth (1903-1991, m. Harold Freeland) and Robert Fielding (1909-1991, m. Opal Awbrey). By 1910, John was an electrician for a telephone company. His last employment was for the City of Chicago, again as an electrician.

On Nov 17, 1915, his wife passed, and on October 6, 1921, John followed her. John had been living with his brother, Jim and his family, for the three weeks preceding his death. His body was taken to Roanoke for burial (per death certificate). At that time, John's father had passed and many of his siblings and their mother lived together in Roanoke. His wife and her family were buried at Mountain View Cemetery in Vinton, Virginia. It is believed, he is likely buried in Vinton, Roanoke County, Virginia near his wife, Mary.
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Newspaper articles:

1893 20 Aug J. E. and J. H. Wayland returned home yesterday from the World's Fair and Dullinsville, Va.

1896 (14 July) ARRIVED IN ROANOKE. F. N. Wayland, father of J. E. Way land, mail carrier, and J A. Wayland, motorman, arrived in the city today from his home in Madison county, Va. Mr. Wayland and his son, J. E. Wayland, will leave to-day for New Franklin, Mo., to visit relatives for thirty days and will return by way of Chicago and take in the sights of that city. [Source: The Roanoke Times, Roanoke Virginia, 14 Jul 1896, page 5.]

1896 (16 July) J. E. Wayland and F. H Wayland, of Roanoke, passed through last night en route to New Franklin. Mo ; to visit relatlves. [Bluefleld Telegraph].

1896 (12 Aug) Joseph Edgar Wayland and his father, Fielding Henry returned 12 August 1896 from a month’s visit to friends in Maryland. [Library of Virginia, The Roanoke Daily Times, Vol 15, No 271, 13 Aug 1896]

1896 (12 Aug) John Hamilton Wayland arrived in Roanoke. [Library of Virginia, The Roanoke Daily Times, Vol 15, No 271, 13 Aug 1896]

1896 (13 Aug) J. H. Wayland and father returned yesterday from a month's visit to friends in Maryland. J. H. Wayland, of Chicago, formerly of the Roanoke Street Railway Company, arrived in the city yesterday

1896 (Aug) FAMILY REUNION. The Howard County (Mo.) Advertiser has the following: A family reunion was held at the residence of N. S. Wayland, at New Franklin Wednesday, three brothers and three sisters being present, together with their father, who is now in his 82nd year. The children present were: F. H. Wayland, of Brightwood, Va., J. W. Wayland, of Franklin; W. T. Wayland, of Fayette, and Mrs. Sarah E. Carter, of Saline County; Mrs. Annie Carpenter, and Miss Lucy Wayland, of New Franklin. The last reunion of the family was held at the old home place in Madison County, Virginia, on March 17, 1869. A large number of grandchildren and other relatives were present at the reunion Wednesday and it was a most joyous event for the family, though many faces were missed from the family circle, who has gone over to that other and better land. J E. Wayland, of the Roanoke post office, and J. H. Wayland, his brother, of Chicago, who are now visiting friends here, were in attendance.

1896 (1 Sep) J. Alexander Wayland returned yesterday from a ten day’s visit to his home at Brightwood. [Library of Virginia, The Roanoke Daily Times, Vol 15, No 287, 1 Sep 1896]

1897 20 May J. E. Wayland, a letter carrier, has just returned from a visit to his home in Madison county, accompanied by his sister. Miss Fanny, who will stay several weeks in Roanoke.

1897 2 Oct DELIGHTFUL TROLLEY RIDE. A trolley party was given Thursday night by the young men of the Street Railway Company. Refreshments were served aboard the oar and the occasion was one of great enjoyment to all who participated. Among the young ladies in attendance were Miss Annie Deacon, of Lynchburg; Misses Mary, Rosa and Elsia Fuqua, Annie Brown, Minnie Pollard and Dowdy, of Vinton; Misses Fannie Wayland, Callio Smith, Ruth Dyer, Mao and Lizzie Bennett. Fannie Stiff, Mollie Hackler. Hattie Wingfield, Laurie Pollard, Ida Franklin. Mary Bannders, Hart and Moore, of Roanoke.

1897 (19 Oct) APPROACHING MARRIAGE. Cards are out announcing the marriage of Jno. II. Wayland, of Chicago, a former street car conductor in this city, to Miss Mary Allen Fuqua, daughter of Mr. and Mrs. R. M. Fuqua of Vinton, on Oc tober 27. Mr. Wayland is a brother of Edgar Wayland a letter carrier in the post office of this city

1897 (27 Oct) WEDDING TO-NIGHT. Jno H. Wayland, of Chicago, has arrived in the city and is the guest of his brother,Edgar Wayland, of the city post office. Mr.Wayland will tonight be married to Miss Mary A. Funua, of Vinton, at the residence of the bride's parents, Mr. and Mrs. R. M. Fuqua.

1897 (28 Oct) WAYLAND-FUQUA. There was a very pretty home wedding last night at Vinton when Miss Marv A. Fuqua became the bride of John H. Wayland, of Chicago. Miss Rosa Fuqua, the sister of the bride, was maid of honor, while J. E. Wayland, a brother of the groom, acted in the capacity of best man. The bridesmaids were Misses Eliza Fuqua, Fannie Wayland and Ida Black and the groomsmen were S. F. Fuqua, R. S. Thomas and T. W. Hawkins. The happy couple, accompanied by Miss Fannie Wayland and J. E. .Wayland, sister and brother of the groom, left on the 10:50 train last night to spend a few days at Mr. Wayland's old home in Madison, after which they will go to Chicago, where they will reside in the future.