16 cities
| City | County | 2025 Pop. ↓ |
|---|---|---|
| Plymouth town | Plymouth County | 67,669 |
| Peabody city | Essex County | 54,382 |
| Pittsfield city | Berkshire County | 42,466 |
| Pembroke town | Plymouth County | 18,254 |
| Palmer Town city | Hampden County | 12,285 |
| Pepperell town | Middlesex County | 11,772 |
| Plainville town | Norfolk County | 9,891 |
| Paxton town | Worcester County | 5,004 |
| Provincetown town | Barnstable County | 3,691 |
| Princeton town | Worcester County | 3,500 |
| Plympton town | Plymouth County | 2,946 |
| Phillipston town | Worcester County | 1,722 |
| Pelham town | Hampshire County | 1,253 |
| Petersham town | Worcester County | 1,171 |
| Peru town | Berkshire County | 790 |
| Plainfield town | Hampshire County | 639 |