11 cities
| City | Rank | 2026 Pop. ↓ | 2020 Pop. | Annual Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Crawfordsville | 1 | 16,718 | 16,345 | 0.37% | 1,620 | 10 | City |
| Ladoga | 2 | 1,104 | 1,079 | 0.36% | 2,056 | 1 | Town |
| Waynetown | 3 | 983 | 956 | 0.51% | 2,209 | 0 | Town |
| Linden | 4 | 732 | 713 | 0.41% | 1,872 | 0 | Town |
| Darlington | 5 | 726 | 707 | 0.41% | 2,167 | 0 | Town |
| New Market | 6 | 563 | 548 | 0.54% | 2,070 | 0 | Town |
| Waveland | 7 | 443 | 431 | 0.45% | 1,438 | 0 | Town |
| New Richmond | 8 | 317 | 311 | 0.32% | 1,651 | 0 | Town |
| New Ross | 9 | 314 | 308 | 0.32% | 1,050 | 0 | Town |
| Wingate | 10 | 252 | 243 | 0.8% | 1,299 | 0 | Town |
| Alamo | 11 | 68 | 65 | 1.49% | 1,097 | 0 | Town |
Crawfordsville is the largest city in Montgomery County, with a population of 16,718.
Alamo is the smallest city in Montgomery County, with a population of 68.
There are 11 cities in Montgomery County, Indiana.