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Answer: [We will not answer the question you did not ask: nowadays, when traveling in relatively built up areas, whether Tefillat Haderech is called for when traveling from point X to Y.]
The gemara (Berachot 30a) asks when one begins to recite Tefillat Haderech and until when, and answers "from the time he seizes the road" (there are different texts and it is hard to translate literally) and up to a parsa (approximately 4 km.), respectively. It is unclear from theRishonim when one is considered on the road. The Magen Avraham (110:14) says it is after he leaves the city, and in fact comes to a place where there has been 70 amot without houses outside the city. (The determination on each road out of a city and whether rules for the city limits are the same as for eiruv techumin are beyond our present scope – see Machatzit Hashekel 110:14).
The Taz (110:7) says that there is no source for waiting until after leaving the city, as the gemara about seizing the road means just that one must be certain he is embarking on the journey. The Tur and Shulchan Aruch (Orach Chayim 110:6) cite the practice of the Maharam MiRutenberg to connect Tefillat Haderech to Birkot Hashachar (sinceTefillat Haderech starts as an open beracha, which is fitting to follow a previous beracha). The Taz understands that this is done duringShacharit and thus before leaving the city. Others, including the Eliya Rabba (110:14), counter that the Maharam did this when he davened on the way. The Shulchan Aruch (OC 230:1) connects Tefillat Haderech to the beracha said for leaving the city one was visiting. The Pri Megadim (OC, Mishbetzot Zahav 110:7) sees that as a sign that he holds that it is recited right after leaving the city, even if there are still houses.
You are likely right that sometimes people recited Tefillat Haderechtoo early. However, b’di’eved (after the fact), this is not so bad. First, almost all Acharonim agree that b’di’eved one fulfills the obligation when reciting once he was preparing to leave (Eliya Rabba ibid., Mishna Berura 110:29). Therefore, the beracha is not l’vatala and you may and should answer Amen (see Shulchan Aruch, OC 215:2). Also, In our times, it may make more sense to say Tefillat Haderech earlier. In the past, the main concerns were bandits and animals, who were more prevalent outside the city, whereas nowadays our primary concern, car accidents, can happen anywhere (see an application in Shevet Halevi X:21). On the other hand, it is hard to change halachic rules based on such a factor.
Bemare Habazak - Rabbis Questions (657)
Rabbi Daniel Mann
239 - Products Containing Minute Quantities of Non-Kosher Food
240 - Imperfectly Said Tefillat Haderech
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The matter of not saying the addition for the return trip is not an issue. The phrase (different siddurim have variations), is mentioned for all tripsby certain Rishonim (Rosh, Berachot 4:18) and not by others (see Kaf Hachayim, OC 110:13). It is only some Acharonim and contemporary practice who set it aside for cases where you are returning the same day. Therefore, there is no good reason to be concerned that the validity of the beracha is affected by omitting it (Ishei Yisrael 50:(3)).
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