| City | Rank | 2026 Pop. ↓ | 2020 Pop. | Annual Change | Density (/mi²) | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Crawfordsville | 1 | 16,789 | 16,341 | 0.54% | 1,627 | 10 | City |
| Ladoga | 2 | 1,109 | 1,076 | 0.54% | 2,065 | 1 | Town |
| Waynetown | 3 | 982 | 949 | 0.61% | 2,207 | 0 | Town |
| Linden | 4 | 746 | 722 | 0.54% | 1,908 | 0 | Town |
| Darlington | 5 | 728 | 706 | 0.55% | 2,173 | 0 | Town |
| New Market | 6 | 571 | 553 | 0.71% | 2,099 | 0 | Town |
| Waveland | 7 | 445 | 433 | 0.45% | 1,445 | 0 | Town |
| New Richmond | 8 | 319 | 310 | 0.31% | 1,661 | 0 | Town |
| New Ross | 9 | 315 | 308 | 0.32% | 1,054 | 0 | Town |
| Wingate | 10 | 253 | 245 | 0.4% | 1,304 | 0 | Town |
| Alamo | 11 | 67 | 64 | 0% | 1,081 | 0 | Town |
Crawfordsville is the largest city in Montgomery County, with a population of 16,789.
Alamo is the smallest city in Montgomery County, with a population of 67.
There are 11 cities in Montgomery County, Indiana.