After being asked to leave Philippi by the city magistrates (Acts 16:39), Paul visited Lydia’s home, which had become the first house-church in the city and comforted and encouraged the believing community there. His delay in obeying the city authorities expresses the advantage of his Roman citizenship, which honor had been vindicated through the magistrates’ apology concerning their illegal behavior. Paul left on the Via Egnatia, the main Roman highway connecting Rome with her eastern provinces. The missionary team was probably on horseback and reached Thessalonica in approximately three days with overnight stops at Amphipolis and Apollonia (Acts 17:1), roughly 30 miles per day.
Luke tells us that Paul found a synagogue at Thessalonica, which may infer there wasn’t one at either Amphipolis or Apollonia, so he and Silas found a place in the market to exercise their trade in leather goods in anticipation of their long stay at Thessalonica (1Thessalonians 2:9). At first, one might assume Paul didn’t stay there for more than three weeks (Acts 17:2), but, since he claims he and Silas supported the missionary team themselves, plus saying he received support from the Philippian church twice while ministering at Thessalonica (Philippians 4:16), one may conclude that he had to have been there at least over a month, perhaps two or three. Much depends upon how soon the opposition was able to stir up the community’s wrath, which eventually got Paul expelled from the city.
Luke says that for three Sabbaths Paul disputed or reasoned with those who went to synagogue (Acts 17:2), opening the Scriptures (verse-3), i.e. offering a different way of looking at them than they were accustomed to understanding, by alleging that the Messiah had to have suffered and died. That is, Paul set before them Christ, crucified and resurrected, concluding that this Jesus, whom Paul had seen on the Damascus road, was indeed the long awaited Messiah.
After three Sabbaths (where they successive …were they the only Sabbaths Paul attended synagogue or was in the city?) some of the Jews believed, but a greater number of God-fearing gentiles and prominent women believed the Gospel (Acts 17:4). Nevertheless, Paul tells us that those three weeks were not without contention (1Thessalonians 2:2). It seems the majority of the Jews there opposed the Gospel, which implies the synagogue rulers or leaders probably openly opposed Paul’s arguments (cp. Acts 17:5). Nevertheless, before they were able to arouse a public display of dissent, it seems Paul had left off teaching in the synagogue to reason with the citizens in the marketplace, for he writes that many who came to Christ had left off worshiping idols (1Thessalonians 1:8-9), which would not have been the case for gentile God-fearers who attended synagogue; they would have long since laid idol-worship aside. Therefore, Paul must have spent a considerable time outside the synagogue reasoning with pagans who turned from idols to the living God.
Nevertheless, the Jewish leaders who opposed Paul grew jealous (i.e. zealous for their Jewish traditions) over what he was doing. Not only had he taken away some of the most prominent God-fearers from among them at synagogue, but he was also showing success in the marketplace by drawing to Jesus the very people they should have been reaching out to in the name of the God of Israel, but hadn’t. What occurred here was not unlike what occurred in Acts 6 when Stephen was taken into custody and charged before the Jewish authorities at Jerusalem. When the Jewish synagogue leaders were unable to resist Stephen’s wisdom and Spirit (Acts 6:10), they secretly induced men to accuse him of wrongdoing (Acts 6:11) and stirred up the people against him (Acts 6:12). This is exactly what occurred in Thessalonica (Acts 17:5), for the Jewish leaders consorted with the rabble in the marketplace, probably marginalized locals, day laborers looking for any kind of employment. They made up the mob who eventually got Paul and Silas expelled from the city (cp. 1Thessalonians 2:15 NIV “drove us out”), and the same enemies prevented Paul’s return as long as the present ruling magistrates were in office (1Thessalonians 2:18).