Top Baseball Towns in Fairfield 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. 16 towns have won something.
Fairfield leads Fairfield County, CT, scoring 38.70 almost entirely on youth titles, and not narrowly — Fairfield is clear of Stamford by 31 points. 16 towns have won something since 2000.
The top ten in Fairfield County, CT are Fairfield, Stamford, Westport, Wilton, Darien, Trumbull, Ridgefield, New Fairfield, Norwalk and Danbury. Between them they account for 91% of every point scored across the 16 towns on this list.
Size is doing a lot of work here. New Fairfield is in the top ten on a population of 13,651, while Stamford has 139,134 to draw on — roughly 10 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. New Fairfield scores purely on high school championships — 1 of them — with no Little League title counted at all. Wilton is the mirror image: 5 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. Fairfield, Westport, Darien and Trumbull have won something in the last two seasons, which is why they sit where they do.
One caveat worth reading before you argue with the order. The youth half of this score is Little League only, because Little League is the only organization that publishes a championship archive — every district, section and state champion back to the 1950s. Cal Ripken and Babe Ruth publish nothing below the World Series. 4 towns in Fairfield County, CT run Cal Ripken or Babe Ruth ball with no Little League program at all, and they score zero youth points here no matter how much they win. Towns that run both lose the Cal Ripken half the same way. If your league has a record we're missing, tell us and we'll add it.
| # | Town | Score | Population | HS titles | LL state | LL district | Won by |
|---|---|---|---|---|---|---|---|
| 1 | Fairfield CT Fairfield County | 38.7 | 65,300 | 2 | 9 | 12 | Fairfield Warde High School · Fairfield National Little League |
| 2 | Stamford CT Fairfield County | 7.7 | 139,134 | 2 | 1 | 5 | Westhill High School · Stamford High School +1 |
| 3 | Westport CT Fairfield County | 7.49 | 27,996 | 4 | — | — | Staples High School |
| 4 | Wilton CT Fairfield County | 5.78 | 19,255 | — | 1 | 3 | Wilton Baseball Association |
| 5 | Darien CT Fairfield County | 5.67 | 22,528 | — | 1 | 1 | Darien Youth Baseball & Softball League |
| 6 | Trumbull CT Fairfield County | 5.06 | 38,073 | 3 | — | 1 | St Joseph High School · Trumbull Little League |
| 7 | Ridgefield CT Fairfield County | 3.56 | 25,300 | — | — | 7 | Ridgefield Baseball Organization |
| 8 | New Fairfield CT Fairfield County | 3 | 13,651 | 1 | — | — | New Fairfield High School |
| 9 | Norwalk CT Fairfield County | 2.75 | 93,661 | 1 | — | 1 | Norwalk High School · Norwalk Little League |
| 10 | Danbury CT Fairfield County | 2.6 | 88,692 | 4 | — | — | Danbury High School · Immaculate High School |
| 11 | Brookfield CT Fairfield County | 2.52 | 18,186 | 1 | — | — | Brookfield High School |
| 12 | Redding CT Fairfield County | 2.38 | 8,830 | 1 | — | — | Joel Barlow High School |
| 13 | New Canaan CT Fairfield County | 1.42 | 21,160 | 1 | — | — | New Canaan High School |
| 14 | Shelton CT Fairfield County | 1.34 | 42,805 | 1 | — | — | Shelton High School |
| 15 | Weston CT Fairfield County | 0.63 | 10,490 | — | — | 1 | Weston CT Baseball |
| 16 | Monroe CT Fairfield County | 0.31 | 19,269 | — | — | 1 | Monroe Baseball & Softball |
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
- 1ReddingCT2.38 · 9k
10,000–25,000
- 1WiltonCT5.78 · 19k
- 2DarienCT5.67 · 23k
- 3New FairfieldCT3 · 14k
- 4BrookfieldCT2.52 · 18k
- 5New CanaanCT1.42 · 21k
- 6WestonCT0.63 · 10k
- 7MonroeCT0.31 · 19k
25,000–75,000
- 1FairfieldCT38.7 · 65k
- 2WestportCT7.49 · 28k
- 3TrumbullCT5.06 · 38k
- 4RidgefieldCT3.56 · 25k
- 5SheltonCT1.34 · 43k
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.