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Letters from January 1923- May 1924 from William to his sister Frances while he attended Fredericksburg High School. Also writes of getting a job with a liner, participation in military training exercises, as well as of target practice and drill. References to the building of the new armory. Mentions a trip to Ft. Bragg, North Carolina- one letter written from Ft. Bragg tells sister he is now "Pvt. W.K. Howard"-it appears he was in the Army Reserve or the National Guard. Mentions his birthday and being promoted to sergeant. Writes of football games, his Indian artifact collection, plans to visit Gay Mont and Canning, as well as his travelling by train to Kansas. Folder contains copy of letter from Fredericksburg High School to William's father concerning tuition and course schedule issues. William also mentions his plans to attend V.P.I. Photograph to sister of hazing tradition 'Rat Parade'.

Letters from William Key Howard to his sister Frances, from V.I.P. which express his dissatisfaction with the school. Feels he is wasting his time at the school, though he enjoys the athletics. His company won inter-company basketball and football championships, he took first place in shot put and second in javelin throwing. Mentions inspection of the school, which is labeled as 8th best in country, as well as a large fire near the school. Mentions letters of his guardian and financial advisor Mr. Young. Money from Mr. Young to buy Liberty Bond. He writes of going to see "The Birth of a Nation." He mentions Black people in the theater were clapping when the character Lynch was carried through the street on the shoulders of celebrating Black people. He writes that "they had K.Ks. up in the gallery to keep the colored people quite [sic]." William works on a ship as deck boy. Mentions going to see "The Birth of a Nation". Contains a letter from the Davey Tree Expert Company dated October 16, 1925 accepting William's acceptance into their tree surgeon program.

Letters from William Key Howard to his sister Frances Howard. Writes of his training with Davey Tree Expert Company in Kent, Ohio. Mentions learning knots and how to work with the ropes. Sent to Pennsylvania for paid field work, as well as Maryland. Worries about keeping this job for the long term. Considers selling his Virginia Excelsior Company stock- thinks he and sister will get $6,000 each. Mentions Mr. Young his guardian (perhaps the same person as Mr. Edgar M. Young president of the Virginia Excelsior Company) William's father is connected with this company. Sister is getting married to Robert Gilchrist Robb in June.

Letters from William Key Howard to his sister Frances Robb (nee Howard). William is working temporarily as crew member on a ship-sails to Antwerp and Rotterdam. Returns and resumes job with Davey Tree Expert Company. Works near Baltimore Maryland. Mentions lay offs by "Ford". Leaves job at Davey Tree Expert Company in September and works for the Merchants and Miners Transportation Corporation. Longs for the sea.

Letters from William Key Howard to sister Frances Robb. William writes of having "sent that lock of Boothe's [sic] hair that Grandma had to the Confederate Museum in Richmond." Mentions marital problems between his father and his second wife (Amy Margaret), she might move back to Texas. Mentions Frances and husband Robert Gilchrist Robb moving into the Paradise (Ludwell-Paradise) House on Duke of Gloucester Street in Williamsburg. Longs for the sea, Frances worries about him when he sails. Desires to work on a ship through the Shipping Board. Some letters written while at sea on the SS Eastern Dawn which sailed to Europe including Antwerp. Contains photographs.

Letters from William Key Howard to sister Frances Robb. William spends winter months working on steamships sailing for Europe, ports including Copenhagan and Finland. Inquires if there is work for tree surgeons in the restoration of Williamsburg- later says doesn't think Williamsburg,and contracting company Underwood, can afford him. Mentions time spent at Fall Hill, and friend Fred Robinson. Many Letters written from Bryn Mawr, Pennsylvania where he is doing tree work. Mentions joining the Virginia National Guard-training at Tobyhanna, Pennsylvania. Writes of opprotunity to partly own a gold mine with his friend Lynn-mine is located in Honduras. William and friend Robbie contemplate going there. Novmeber 3, he mentions stock market and the crash.

Letters from William Key Howard to sister Frances Robb. Mentions getting a job as a watchman at Kenmore (the one time home of George Washington's sister) which is being renovated. Estate once belonged to William's grandfather William Key Howard Sr. as well as his Uncle Willam Key Howard Jr. He must keep watch at night- so he sleeps there. Mentions cousin John Randolph died.

Letters from William Key Howard to sister Frances Robb. Writes of moving to Belle Hill, near Fredericksburg, Virginia. Works for the National Park Service, specifically as park superintendant of the Fredericksburg and Spotsylvania National Military Park. Includes Newspaper clippings and announcement of his marriage to Elizabeth Burke Crismond on March 18, 1937. Father dies, mentions funeral-he is executor of father's estate-details. Mentions housewarming for new home at the park for Branch Spalding (coordinating superintendent for Virginia Civil War parks).

Letters from William Key Howard to sister Frances Robb. Mentions a war and a trip to the Baltic including stops at "Danzig, Helsingford [sic] and Murmansk". Mentions attending a fire training school and refers to a serious problem with Bob's (Robert Gilchrist Robb) eye. Writes about his being discharged from the Virginia National Guard (?). Mentions plans for new job.

Letters from William Key Howard to sister Frances Robb. Writes he has volunteered for the Army, mentions that wife, Liz and their two daughters, will live in Spotsylvania Court House while he is away. Mentions renting his Belle Hill home to a soldier, and wants to rent the large house too. Mentions Army induction at Bowling Green and then moves to Camp Lee. He is stationed at Salem Airbase in Oregon for training. Mentions training experiences and his "expert" marksmanship. Believes he will be stationed behind the lines in war. Reassigned to "Ono siding" near San Bernardino, California. Describes location and his job there. Mentions plans to visit Los Angeles and Mexico, as well as visiting Hollywood where they made "The Birth of a Nation".