In this chapter, Moses focuses in how to observe the pilgrimage festivals.
This chapter consists of two sections. The first section (vv. 1-17) describes the three annual pilgrim festivals the Israelites are to celebrate in order to commemorate their redemption from Egypt and to thank God for the harvest grain. The second section (vv. 18-22) deals with the administration of social justice in the land of Canaan. The judges and officers are commanded to execute justice with equity in order to please the righteous God (vv. 18-20). The last section prohibits Israel from associating pagan objects of worship with the worship of the Suzerain LORD at the central sanctuary (vv. 21-22).
Chapter 16 can be outlined as follows:
-Celebration of Feasts (Deut. 16:1 – 17)
-Passover and the Feast of Unleavened Bread (Deut. 16:1 – 8)
-Feast of Weeks – Pentecost (Deut. 16:9 – 12)
-Feast of Tabernacles (Deut. 16:13 – 17)
-Respect for Authority (Deut. 16:18 – 22)
-The Appointment of Judges and Officials (Deut. 16:18 – 20)
-The Prohibition of Bringing Pagan Worship Objects to the Central Sanctuary (Deut. 16:21 – 22)

Deuteronomy 16:1-8

The Israelites are commanded to celebrate the Passover and the Feast of Unleavened Bread at the central sanctuary. This celebration will serve to commemorate the LORD’s deliverance of Israel out of Egypt.

Deuteronomy 16:9-12

The Israelites were to celebrate the grain harvest in the Feast of Weeks to acknowledge the Giver of the harvest—the Suzerain (Ruler) LORD. This feast is to be accompanied by a freewill offering.

Deuteronomy 16:13-15

The Israelites were commanded to joyfully celebrate the Feast of Booths with all those who belong to them. This feast commemorated the journey from Egypt to the Promised Land by living in structures made of wood and foliage. They are to have that celebration at the central sanctuary.

Deuteronomy 16:16-17

The celebrations of the Feast of Unleavened Bread, the Feast of Weeks and the Feast of Booths every year at the central sanctuary are summarized.

Deuteronomy 16:18-20

Here, the Israelites are commanded to appoint judges and officers for themselves in all their towns. These judges and officers are to administer justice with equity in the Promised Land.

Deuteronomy 16:21-22

The Israelites are prohibited from building an Asherah pole of any kind. They are to give exclusive worship to their Suzerain (Ruler) God.