This shiur is based on one written by Rabbi Riskin in 2010, and expanded in his book, Torah Lights.
א אלה מסעי בני ישראל אשר יצאו מארץ מצרים לצבאתם; ביד משה ואהרן׃
ב ויכתב משה את מוצאיהם למסעיהם על פי ה׳; ואלה מסעיהם למוצאיהם׃
ג ויסעו מרעמסס בחדש הראשון בחמשה עשר יום לחדש הראשון; ממחרת הפסח יצאו בני ישראל ביד רמה לעיני כל מצרים׃
If you think about it, the second pasuk is very hard to understand. Why does the Torah need to tell us that Moshe wrote something in the Torah? We know Moshe wrote the Torah, that’s an article of faith:
כד ויהי ככלות משה לכתב את דברי התורה הזאת על ספר; עד תמם׃
כה ויצו משה את הלוים נשאי ארון ברית ה׳ לאמר׃
כו לקח את ספר התורה הזה ושמתם אתו מצד ארון ברית ה׳ אלהיכם; והיה שם בך לעד׃
And secondly, why bother listing all the places they traveled through? The entire previous book of במדבר told us what happened in all the places where something interesting happened; why a list of nearly meaningless place names?
The answer to the first question seems to be a matter of timing. The Torah as a whole was written down at the end of Moshe’s life; this list must have been written as a separate “pamphlet” when בני ישראל arrived at ערבות מואב, before Moshe started his farewell addresses:
א אלה הדברים אשר דבר משה אל כל ישראל בעבר הירדן; במדבר בערבה מול סוף בין פארן ובין תפל ולבן וחצרת ודי זהב׃
ב אחד עשר יום מחרב דרך הר שעיר עד קדש ברנע׃
ג ויהי בארבעים שנה בעשתי עשר חדש באחד לחדש; דבר משה אל בני ישראל ככל אשר צוה ה׳ אתו אלהם׃
ד אחרי הכתו את סיחן מלך האמרי אשר יושב בחשבון ואת עוג מלך הבשן אשר יושב בעשתרת באדרעי׃
ה בעבר הירדן בארץ מואב הואיל משה באר את התורה הזאת לאמר׃
But this does not answer the question. Why was it necessary to write down their travels separately from the Torah itself? Rashi on this pasuk brings two explanations.
למה נכתבו המסעות הללו, להודיע חסדיו של מקום, שאעפ״י שגזר עליהם לטלטלם ולהניעם במדבר, לא תאמר שהיו נעים ומטולטלים ממסע למסע כל ארבעים שנה ולא היתה להם מנוחה, שהרי אין כאן אלא ארבעים ושתים מסעות. צא מהם י״ד, שכולם היו בשנה ראשונה, קודם גזירה, משנסעו מרמעסס עד שבאו לרתמה. שמשם נשתלחו המרגלים, שנאמר (במדבר יב:טז) ואחר נסעו העם מחצרות וגו׳ (שם יג:ב) שלח לך אנשים וגו׳. וכאן הוא אומר ויסעו מחצרות ויחנו ברתמה, למדת שהיא במדבר פארן. ועוד הוצא משם שמונה מסעות שהיו לאחר מיתת אהרן מהר ההר עד ערבות מואב בשנת הארבעים, נמצא שכל שמנה ושלשים שנה לא נסעו אלא עשרים מסעות. זה מיסודו של רבי משה הדרשן.
ורבי תנחומא דרש בו דרשה אחרת משל למלך שהיה בנו חולה והוליכו למקום רחוק לרפאותו, כיון שהיו חוזרין התחיל אביו מונה כל המסעות. אמר לו כאן ישננו, כאן הוקרנו, כאן חששת את ראשך וכו׳
And the Rambam brings an explanation related to Rashi’s first, that the list teaches us of ה׳'s mercy (though he has a different approach):
When we therefore notice narratives in the Torah, which are in no connexion with any of the commandments, we are inclined to think that they are entirely superfluous, or too lengthy, or contain repetitions; but this is only because we do not see the particular incidents which make those narratives noteworthy. Of this kind is the enumeration of the stations [of the Israelites in the wilderness] (Num. xxxiii.). At first sight it appears to be entirely useless; but in order to obviate such a notion Scripture says, “And Moses wrote their goings out according to their journeys by the commandment of the Lord” (ibid. ver. 2). It was indeed most necessary that these should be written. For miracles are only convincing to those who witnessed them; whilst coming generations, who know them only from the account given by others, may consider them as untrue. But miracles cannot continue and last for all generations; it is even inconceivable [that they should be permanent]. Now the greatest of the miracles described in the Law is the stay of the Israelites in the wilderness for forty years, with a daily supply of manna. This wilderness, as described in Scripture, consisted of places “wherein were fiery serpents and scorpions, and drought, where there was no water” (Deut. viii. 115); places very remote from cultivated land, and naturally not adapted for the habitation of man, “It is no place of seed, or of figs, or of vines, or of pomegranates, neither is there any water to drink” (Num. xx. 5); “A land that no man passed through, and where no man dwelt” (Jer. ii. 6). [In reference to the stay of the Israelites in the wilderness], Scripture relates, “Ye have not eaten bread, neither have ye drunk wine or strong drink” (Deut. xix. 5). All these miracles were wonderful, public, and witnessed by the people. But God knew that in future people might doubt the correctness of the account of these miracles. in the same manner as they doubt the accuracy of other narratives; they might think that the Israelites stayed in the wilderness in a place not far from inhabited land, where it was possible for man to live [in the ordinary way]; that it was like those deserts in which Arabs live at present; or that they dwelt in such places in which they could plow, sow, and reap, or live on some vegetable that was growing there; or that manna came always down in those places as an ordinary natural product; or that there were wells of water in those places. In order to remove all these doubts and to firmly establish the accuracy of the account of these miracles, Scripture enumerates all the stations, so that coming generations may see them, and learn the greatness of the miracle which enabled human beings to live in those places forty years.
Why does Rashi bring two explanations? I think it is because we have two questions: why write this list separately and why write it in the Torah? There are two audiences for the list, them (the people about to enter Israel) and us. The fact that Moshe wrote the journeys out was to distribute to בני ישראל, as a sort of source sheet for the speech he was about to give:
…שהן דברי תוכחות ומנה כאן כל המקומות שהכעיסו לפני המקום בהן…
Hence it is like the father reviewing the past with his son as they return home.
The first reason goes with our second question. It is written in the Torah, for posterity, so that we can, in later generation, testify to ה׳'s kindness in supporting us in the winlderness.
After quoting Rashi and Rambam, Ramban adds:
והנה מכתב המסעות מצות השם היא מן הטעמים הנזכרים או מזולתן ענין לא נתגלה לנו סודו כי על פי ה׳ דבק עם ויכתוב משה לא כדברי ר״א שאמר שהוא דבק עם למסעיהם שכבר הודיענו זה (לעיל ט:כ) על פי ה׳ יחנו ועל פי ה׳ יסעו.
Ramban does not tell us what the סוד that required an explicit command from ה׳ to write this, but the Sfas Emes says something that may give us a hint. In Chassidic fashion, the journey is symbolic of our journey through life:
The Sfas Emes explains the first sequence as reflecting a basic reality: for our story to begin, we first had to get out of Egypt. Therefore, the pasuk starts with “motza’ei’herm” — a word that comes from the shoresh “Y’TZ’A”, and hence, a word that irresistibly evokes “ye’tzi’as Mitzrayim” (our exodus from Egypt). Once we had made that break-out, we could proceed on our journeys.
Apparently, our liberation from Egypt was not a “one shot” process in which once and for all, we moved to a higher stage of development in our relationship with HaShem. On the contrary, the Sfas Emes finds it relevant to observe that every “masa” (journey) took us further from Egypt. Evidently, escape from the cesspool of tum’a which Egypt was known to be had to be gradual, involving many small steps. The Sfas Emes may have inferred this point from the pasuk’s use of the word “motza’ei’hem” — plural.
Proceeding in this vein, the Sfas Emes notes that our journeys continued until we reached our goal—Eretz Yisroel. The fact that we had this objective was crucial. For, too often, people break out from a bad situation; but lacking the right objective, go from the frying pan into the fire. Two examples come swiftly to mind. One case is the story of many Jews in the Shtetel. Reacting to the Shtetel’s social inequities, they broke away from Yiddishkeit, and sought social justice — in Stalin’s tyranny. Another case involves many young Jews who broke away from the materialism of their milieu in America to seek spirituality—in a cult.
Rabbi Riskin points out another question on the pasuk: the second half repeats the first half, but reversed: מוצאיהם למסעיהם followed by מסעיהם למוצאיהם. מוצאיהם למסעיהם I understand: Moshe wrote the places they left to go traveling. But what does it mean that they traveled to the places they left? That’s backwards; they traveled from the places they left.
Rabbi Riskin proposes that it is meant as a matter of mindset: they were traveling to the places they had left. They were going back home. In the first Egyptian exile, Avraham did this literally:
א ויעל אברם ממצרים הוא ואשתו וכל אשר לו ולוט עמו הנגבה׃
ב ואברם כבד מאד במקנה בכסף ובזהב׃
ג וילך למסעיו מנגב ועד בית אל עד המקום אשר היה שם אהלה בתחלה בין בית אל ובין העי׃
כשחזר ממצרים לארץ כנען היה הולך ולן באכסניות שלן בהם בהליכתו למצרים…
And, מעשה אבות סימן לבנים, בני ישראל did the same thing (though not literally) when they left Egypt. And, even more מעשה אבות סימן לבנים, that is how we should view the long journey of the Jewish people over the millenia:
When S.Y. Agnon received the Nobel Prize for Literature, he was asked about his birthplace. To the interviewer’s surprise, he answered that he was born in Jerusalem. The interviewer pointed out that everyone knew he had been born in Buczacz, a town in Galicia. Agnon corrected him: “I was born in Jerusalem more than 3,000 years ago. That was my beginning, my origin. Buczacz in Galicia is only one of the stopping-off points.”