Howard Pyle crossed paths with Yale University a number of times during - and after - his lifetime. In 1903 he delivered the Anniversary Address at the School of Fine Arts; his pictures were exhibited there in 1903 and 1909; in 1905 he designed the bookplate for the Yale Club's library; and his two eldest sons, Theodore and Howard, Jr., were attending the college when he died in Italy. Several of Pyle's letters reside there now, as do some original works of art - and early ones at that - which can be seen here.
And, in looking the Yale page over, I see that the works aren't very well identified. So here's more:
"At the Sign of the Griffin" was published with the title "The Press-Gang in New York" in Harper's Monthly for March 1882. It is one of three Pyle illustrations for the article "Old New York Coffee Houses" by John Austin Stevens. He painted it at the end of 1879.
"He Stops at the Sign of the Weathervane" illustrated Pyle's own poem "Tilghman's Ride from Yorktown to Pennsylvania" in Harper's Monthly for November 1881. The original probably dates from that year.
"The Dunkers - Going to Meeting," although published (without "The Dunkers" in the title) in the October 1889 issue of Harper's Monthly, was painted some nine years earlier, when Pyle initially prepared his article "A Peculiar People" following his November 1880 visit to Ephrata, Pennsylvania.
"Avary Sells His Jewels" was featured for Pyle's article "Buccaneers and Marooners of the Spanish Main" in Harper's Monthly for September 1887. I'm pretty sure Pyle painted this in early 1887 - maybe late 1886.
"An Old Government Toll Gate with Westward Bound Express" appeared in Harper's Monthly for November 1879. It was one of a dozen illustrations Pyle made for William Henry Rideing's "The Old National Pike." The two men travelled along the pike earlier in 1879 (which I mentioned in this post).
And "Isaac Walton" and "Richard de Bury Tutoring Young Edward III" are etchings made by William Henry Warren Bicknell after paintings by Howard Pyle for the Bibliophile Society in 1903.