Months, seasons, years

If you're skipping a few months, seasons, or years, then write love letters to cover the gap. These can be fairly involved, including not only a roll and its results, but also invitations to narrate events and/or to involve the other players. "Dear Marshal, it's been a peaceful year but tell us—what trouble has stemmed from having a standing watch that you never predicted? Then, ask each of the other PCs one of the following …"

If the time skip straddles the change of just one season, have the players make the Seasons Change move and incorporate its results into your letters. For a skip that spans multiple seasons, work changes to steading elements (Fortunes, Surplus, improvements, etc.) into the love letters. Either way, prep a new adventure to bring things back with a bang.