27 cities
| City | County | 2026 Pop. ↓ |
|---|---|---|
| Haverhill | Essex County | 69,187 |
| Holyoke | Hampden County | 38,168 |
| Hingham | Plymouth County | 24,690 |
| Hudson | Middlesex County | 20,822 |
| Holden | Worcester County | 20,804 |
| Hopkinton | Middlesex County | 20,635 |
| Holliston | Middlesex County | 15,643 |
| Hanover | Plymouth County | 15,057 |
| Harwich | Barnstable County | 13,558 |
| Holbrook | Norfolk County | 11,701 |
| Hanson | Plymouth County | 10,901 |
| Hull | Plymouth County | 10,548 |
| Halifax | Plymouth County | 7,860 |
| Hamilton | Essex County | 7,774 |
| Harvard | Worcester County | 7,100 |
| Hopedale | Worcester County | 6,139 |
| Hadley | Hampshire County | 5,246 |
| Hampden | Hampden County | 5,004 |
| Hubbardston | Worcester County | 4,551 |
| Hatfield | Hampshire County | 3,295 |
| Hardwick | Worcester County | 2,798 |
| Holland | Hampden County | 2,595 |
| Huntington | Hampshire County | 2,053 |
| Hinsdale | Berkshire County | 1,892 |
| Hancock | Berkshire County | 740 |
| Heath | Franklin County | 713 |
| Hawley | Franklin County | 352 |