You may have heard the expression either of "a land flowing with milk and honey" or "a land of flowing milk and honey", but where does it come from? And what does it even mean?
In the Torah portion of Ki Tavo, it appears three times(!), offering us an excellent opportunity to look into this expression.
He brought us to this place and gave us this land, a land of flowing milk and honey.
(15) Look down from Your holy abode, from heaven, and bless Your people Israel and the soil You have given us, a land of flowing milk and honey, as You swore to our fathers.”
(3) and inscribe upon them all the words of this Teaching. When you cross over to enter the land that the LORD your God is giving you, a land of flowing milk and honey, as the LORD, the God of your fathers, promised you—
This phrase actually occurs eleven times throughout the Torah, with the above occurrences as the final three in the Torah, having appeared four times in the book of Exodus (3.8, 3.17, 13.5, and 33.3), one in Leviticus (20.24), one in Numbers (14.8), and two previous times in the book of Deuteronomy (6.3 and 11.9).
Rami bar Yehezkel visited B'nei B'rak and saw goats grazing beneath a fig tree with honey oozing from the figs and milk dripping from them, and they were mixing together with each other. He said, "This is milk and honey flowing!"
א"ר יעקב בן דוסתאי מלוד לאונו שלשה מילין פעם אחת קדמתי בנשף והלכתי עד קרסולי בדבש של תאינים
אמר ר"ל לדידי חזי לי זבת חלב ודבש של צפורי והוי שיתסר מילין אשיתסר מילין
אמר רבה בר בר חנה לדידי חזי לי זבת חלב ודבש של כל ארץ ישראל והויא כמבי מיכסי עד אקרא דתולבנקי כ"ב פרסי אורכא ופותיא שיתא פרסי
Rabbi Ya’akov ben Dostai said: "There are three mil from Lud to Ono. Once I rose early in the morning and I walked in ankle-deep honey oozing from fig trees."
Reish Lakish said: "I myself saw a region called: The place flowing milk and honey by Tzippori, and it was an area that covered sixteen by sixteen mil, 256 square mil."
Rabba bar bar Ḥana said: "I myself saw the region flowing milk and honey of all Eretz Yisrael, and it was the same in area as that which stretches from the city of Bei Mikhsei until the fortress of Tulbanki: Its length twenty-two parasangs and its width six parasangs, 132 square parasangs, which is 2,112 square mil."
זבת חלב ודבש. חָלָב זָב מִן הָעִזִּים, וְהַדְּבַשׁ זָב מִן הַתְּמָרִים וּמִן הַתְּאֵנִים:
Milk flows from the goats and honey flows from the dates and from the figs.
וטעם זבת חלב ודבש כי שבח תחלה את הארץ שהיא טובה, לומר שהאויר טוב ויפה לבני אדם וכל טוב ימצא בה, ושהיא רחבה, שיעמדו בה כל ישראל במרחב או טעם רחבה שיש בה רחבות, שפלה ועמק ומישור גדולים וקטנים ואין רובה הרים וגאיות וחזר ושבח אותה שהיא ארץ מקנה שיש בה מרעה טוב, והמים יפים, ויגדל החלב בבהמות, כי אין הבהמות בריאות וטובות ומרבות החלב רק באויר טוב ועשב רב ומים טובים. ובעבור שימצא זה באחו ובמרום הרים אין הפירות שם שמנים ויפים מאד, אמר כי היא עוד שמינה שפירותיה שמנים ומתוקים עד שתזוב כולה בדבש מהם.
The meaning of flowing of milk and honey is that it is initially praising the land that it is good, which is to say that the air is good and lovely to people, and that all good will be found of it.
And it is wide, that all of Israel will be able to live there with space, or the meaning of wide is that there will be lots, low, deep, and huge plains and small plains, and there won't be a lot of mountains or ravines, and then it returns to praise it as a land of livestock which has good grazing and beautiful water, and one can grow milk of domestic animals, since domestic animals are only healthy and good that give off plenty of milk with good air, plentiful grass, and good water.
And on account of this being found in meadows and in the high mountains, there are no fruits there that are fat and good, but it said, that it would be further fatty that the fruits would be juicy and sweet until they ooze honey out of them.