And from thence to Philippi - The former name of this city was Dathos. It was repaired and adorned by Philip, the father of Alexander the Great, and after him was called Philippi. It was famous for having been the place where several battles were fought during the civil wars of the Romans, and, among others, for the decisive battle between Brutus and Antony. At this place Brutus killed himself. To the church in this place Paul afterward wrote the Epistle which bears its name.
Which is the chief city of that part of Macedonia - This whole region had been conquered by the Romans under Paulus Aemilius. By him it was divided into four parts or provinces (Livy). The Syriac version renders it "a city of the first part of Macedonia," and there is a medal extant which also describes this region by this name. It has been proposed, therefore, to alter the Greek text in accordance with this, since it is known that Amphipolis was made the chief city by Paulus Aemilius. But it may be remarked that, although Amphipolis was the chief city in the time of Paulus Aemilius, it may have happened that in the lapse of 220 years from that time Philippi might have become the most extensive and splendid city. The Greek here may also mean simply that this was the first city to which they arrived in their travels.
And a colony - This is a Latin word, and means that this was a Roman colony. The word denotes "a city or province" which was planted or occupied by Roman citizens. It is a strong confirmation of the fact here stated by Luke, that Philippi had the rank and dignity of a Roman colony, as coins are still extant, in which Philippi is distinctly referred to as a colony. Such coins exist from the reign of Augustus to the reign of Caracalla.
Certain days - Some days.

And from thence to Philippi - This was a town of Macedonia, in the territory of the Edones, on the confines of Thrace, situated on the side of a steep eminence. It took its name from Philip II., king of Macedon. It is famous for two battles, fought between the imperial army, commanded by Octavianus, afterwards Augustus, and Mark Antony, and the republican army, commanded by Brutus and Cassius, in which these were successful; and a second, between Octavianus and Antony on the one part, and Brutus on the other. In this battle the republican troops were cut to pieces, after which Brutus killed himself. It was to the Church in this city that St. Paul wrote the epistle that still goes under their name. This place is still in being, though much decayed, and is the see of an archbishop.
The chief city of that part of Macedonia - This passage has greatly puzzled both critics and commentators. It is well known that, when Paulus Aemilius had conquered Macedonia, he divided it into four parts, μερη, and that he called the country that lay between the rivers Strymon and Nessus, the first part, and made Amphipolis its chief city, or metropolis; Philippi, therefore, was not its chief city. But Bishop Pearce has, with great show of reason, argued that, though Amphipolis was made the chief city of it by Paulus Aemilius, yet Philippi might have been the chief city in the days of St. Paul, which was two hundred and twenty years after the division by P. Aemilius. Besides, as it was at this place that Augustus gained that victory which put him in possession of the whole Roman empire, might not he have given to it that dignity which was before enjoyed by Amphipolis? This is the most rational way of solving this difficulty; and therefore I shall not trouble the reader with the different modes that have been proposed to alter and amend the Greek text.
And a colony - That is, a colony of Rome; for it appears that a colony was planted here by Julius Caesar, and afterwards enlarged by Augustus; the people, therefore, were considered as freemen of Rome, and, from this, call themselves Romans, Acts 16:21. The Jewish definition of קלניא kolonia (for they have the Latin word in Hebrew letters, as St. Luke has it. here, κολωνια, in Greek letters) is, a free city, which does not pay tribute.

And from thence to Philippi,.... This place is by Appianus called Datos, which was its original name; and by Diodorus Siculus, Crenidae (c), from the fountains of water, which were many and wholesome, that were about it; and it had its name Philippi, from Philip king of Macedon, father of Alexander the great, who rebuilt it (d): it is now vulgarly called Chrixopolis, that is, Chrysopolis, from the veins and mines of gold found about it; it was famous for a battle here fought between Augustus Caesar and Anthony on the one side, and Brutus and Cassius on the other, in which the latter were vanquished:
which is the chief city of that part of Macedonia; which is called Edonis, in which Ptolomy places it;
and a colony: that is, of the Romans; see Acts 16:37 and which Pliny (e) also calls a colony:
and we were in that city abiding many days; without doing anything, having no opportunity, or door opened to them to preach the Gospel; which must be a great trial of their faith, after Paul had seen such a vision, by which they were so strongly assured it was the will of God they should come and preach the Gospel here, and after they had travelled so far by sea and land; though some observe, that the word used signifies not only to abide, but to exercise themselves, by teaching and preaching the word, which it is supposed they did with success; and that the women they after met with by the river side, were such, at least some of them, who had been converted under their ministry; but the former seems to be the truest sense.
(c) Ptolom. Geograph. l. 3. c. 13. (d) Pausaniae Eliac. 2. l. 6. p. 352. Plin. Nat. Hist. l. 4. c. 11. (e) Ib.

Philippi . . . the chief--rather, perhaps, "the first"
city of that part of Macedonia--The meaning appears to be--the first city one comes to, proceeding from Neapolis. The sense given in our version hardly consists with fact.
a colony--that is, possessing all the privileges of Roman citizenship, and, as such, both exempted from scourging and (in ordinary cases) from arrest, and entitled to appeal from the local magistrate to the emperor. Though the Pisidian Antioch and Troas were also "colonies," the fact is mentioned in this history of Philippi only on account of the frequent references to Roman privileges and duties in the sequel of the chapter.
AT PHILIPPI, LYDIA IS GAINED AND WITH HER HOUSEHOLD BAPTIZED--AN EVIL SPIRIT IS EXPELLED, PAUL AND SILAS ARE SCOURGED, IMPRISONED, AND MANACLED, BUT MIRACULOUSLY SET FREE, AND THE JAILER WITH ALL HIS HOUSEHOLD CONVERTED AND BAPTIZED. (Acts 16:12-34)
we were in that city abiding certain days--waiting till the sabbath came round: their whole stay must have extended to some weeks. As their rule was to begin with the Jews and proselytes, they did nothing till the time when they knew that they would convene for worship.

The first city - Neapolis was the first city they came to in that part of Macedonia which was nearest to Asia: in that part which was farthest from it, Philippi. The river Strymon ran between them. Philippi was a Roman colony.