27 cities
| City | County | 2025 Pop. ↓ |
|---|---|---|
| Haverhill city | Essex County | 67,947 |
| Holyoke city | Hampden County | 37,506 |
| Hingham town | Plymouth County | 24,279 |
| Hudson town | Middlesex County | 20,014 |
| Holden town | Worcester County | 19,944 |
| Hopkinton town | Middlesex County | 19,926 |
| Holliston town | Middlesex County | 15,173 |
| Hanover town | Plymouth County | 14,719 |
| Harwich town | Barnstable County | 13,523 |
| Holbrook town | Norfolk County | 11,260 |
| Hanson town | Plymouth County | 10,574 |
| Hull town | Plymouth County | 10,186 |
| Halifax town | Plymouth County | 7,746 |
| Hamilton town | Essex County | 7,706 |
| Harvard town | Worcester County | 6,990 |
| Hopedale town | Worcester County | 6,036 |
| Hadley town | Hampshire County | 5,257 |
| Hampden town | Hampden County | 4,919 |
| Hubbardston town | Worcester County | 4,346 |
| Hatfield town | Hampshire County | 3,311 |
| Hardwick town | Worcester County | 2,662 |
| Holland town | Hampden County | 2,555 |
| Huntington town | Hampshire County | 2,059 |
| Hinsdale town | Berkshire County | 1,882 |
| Hancock town | Berkshire County | 731 |
| Heath town | Franklin County | 716 |
| Hawley town | Franklin County | 349 |