Шмуэль А 1:3 Комментарий: Rashi, Radak, Metzudat David & Ralbag

This man would go up. This is the present tense, i.e., he would go up from one appointed season to another, to Shilo.⁸He would go to Shiloh on the three pilgrimage festivals of Pesach, Shavuos and Sukkos. The Midrash Aggadah [renders] that the route he followed this year he did not take the next year in order to publicize [his pilgrimage] to the Bnei Yisroel that they should do likewise.⁹See Talmud Yerushalmi, Berachos 9:5.

And he went up: So would he do every year, as he would go up to Shiloh to sacrifice. And that which it stated, "from his city," is to say that he would encourage the people of his city to go up. And in the homiletical teachings - he would not go next year the way that he went this year, but would rather go a different way each year in order to make Israel know [about this] and to bring them up to Shiloh.

This man used to go up: His custom was always to go up to Shiloh every year, to bow down and sacrifice to God.