27 cities
| City | County | 2025 Pop. ↓ |
|---|---|---|
| Haverhill | Essex County | 68,739 |
| Holyoke | Hampden County | 38,003 |
| Hingham | Plymouth County | 24,552 |
| Hudson | Middlesex County | 20,593 |
| Holden | Worcester County | 20,565 |
| Hopkinton | Middlesex County | 20,303 |
| Holliston | Middlesex County | 15,495 |
| Hanover | Plymouth County | 14,972 |
| Harwich | Barnstable County | 13,589 |
| Holbrook | Norfolk County | 11,588 |
| Hanson | Plymouth County | 10,810 |
| Hull | Plymouth County | 10,413 |
| Halifax | Plymouth County | 7,823 |
| Hamilton | Essex County | 7,722 |
| Harvard | Worcester County | 7,052 |
| Hopedale | Worcester County | 6,101 |
| Hadley | Hampshire County | 5,265 |
| Hampden | Hampden County | 4,984 |
| Hubbardston | Worcester County | 4,492 |
| Hatfield | Hampshire County | 3,308 |
| Hardwick | Worcester County | 2,760 |
| Holland | Hampden County | 2,588 |
| Huntington | Hampshire County | 2,062 |
| Hinsdale | Berkshire County | 1,891 |
| Hancock | Berkshire County | 740 |
| Heath | Franklin County | 715 |
| Hawley | Franklin County | 352 |