Top Baseball Towns in Middlesex County, CT
Ranked on championships won since 2000 — high school state titles and Little League district, section and state titles counted together, with recent wins weighted more heavily. 9 towns have won something.
Cromwell leads Middlesex County, CT, scoring 3.43 on both halves of the game roughly evenly, and not narrowly — Cromwell is clear of Portland by 1.93 points. 9 towns have won something since 2000.
The top 9 in Middlesex County, CT are Cromwell, Portland, East Hampton, Haddam, Killingworth, Durham, Middlefield, Westbrook and Old Saybrook.
Size is doing a lot of work here. Middlefield is in the top ten on a population of 4,274, while Cromwell has 14,388 to draw on — roughly 3 times as many people. That is why the tables below are also split into population bands: a town should be measured against places its own size before it is measured against a city.
Two towns in the top ten got there by opposite routes. Portland scores purely on high school championships — 1 of them — with no Little League title counted at all. Old Saybrook is the mirror image: 1 youth titles and no high school championship in the window.
Recency matters in this table — a title's weight halves every 12 years, so the standings drift on their own every season. Cromwell has won something in the last two seasons, which is why it sits where it does.
Haddam, Killingworth and Durham share credit with neighbouring towns for a regional high school. A regional's championship is split evenly between every town it serves rather than going to the town the building happens to sit in.
| # | Town | Score | Population | HS titles | LL state | LL district | Won by |
|---|---|---|---|---|---|---|---|
| 1 | Cromwell CT Middlesex County | 3.43 | 14,388 | 1 | — | 3 | Cromwell High School · Cromwell Little League |
| 2 | Portland CT Middlesex County | 1.5 | 9,478 | 1 | — | — | Portland High School |
| 3 | East Hampton CT Middlesex County | 1.26 | 13,109 | 1 | — | — | East Hampton High School |
| 4 | Haddam CT Middlesex County | 1.26 | 8,806 | 0.50 ⌗ | — | — | Haddam-Killingworth High School |
| 5 | Killingworth CT Middlesex County | 1.26 | 6,284 | 0.50 ⌗ | — | — | Haddam-Killingworth High School |
| 6 | Durham CT Middlesex County | 1.12 | 7,230 | 0.50 ⌗ | — | — | Coginchaug Regional High School |
| 7 | Middlefield CT Middlesex County | 1.12 | 4,274 | 0.50 ⌗ | — | — | Coginchaug Regional High School |
| 8 | Westbrook CT Middlesex County | 0.75 | 6,918 | 1 | — | — | Westbrook High School |
| 9 | Old Saybrook CT Middlesex County | 0.31 | 10,689 | — | — | 1 | Old Saybrook Little League |
By town size
A championship out of a town of 6,000 is a different achievement from the same title in a city of 600,000. Same scoring, ranked against places of the same size.
Under 10,000
- 1PortlandCT1.5 · 9k
- 2HaddamCT1.26 · 9k
- 3KillingworthCT1.26 · 6k
- 4DurhamCT1.12 · 7k
- 5MiddlefieldCT1.12 · 4k
- 6WestbrookCT0.75 · 7k
10,000–25,000
- 1CromwellCT3.43 · 14k
- 2East HamptonCT1.26 · 13k
- 3Old SaybrookCT0.31 · 11k
How this is scored
- High school state championship — 3 points
- Little League state title — 3 points
- Little League sectional title — 2 points
- Little League district title — 1 point
Only titles since 2000 count, each one's weight halves every 12 years, private-school titles count for 0.75 of a public one, and a regional school's championship is split between the towns it serves.
Full method, sources and what the rankings can't see →By county in Connecticut
Counties with enough towns on the board to rank. Smaller counties are folded into their state list rather than given a page of three rows.