14U Headless Horseman Classic
14U Headless Horseman Classic is a youth travel softball tournament in New Windsor, NY, held Sat, Sep 27 – Sun, Sep 28, 2025. Age groups: 14U. Part of the USSSA Fastpitch calendar.
This tournament has finished. Here is what is on nearby next: softball tournaments in New York in the next 30 days.
From the organizer's listing on usssa.com · checked Jun 20, 2026.
Age groups
| Division | Teams registered |
|---|---|
| 14U Open | 16 |
Entry fees are on the organizer's page.
How strong is the field?
- 14U: Strong field. 16 teams registered, 15 with results we can rate. Strongest entered: Empire White 13U Tighe, RI Thunder-LFC 14u-Palmer and Empire State Huskies 13U Petrillo.
Ratings come from public game results. How field ratings work. The 1-10 rating for each field and every registered team are in the TourneyMagic search.
Other softball tournaments near New Windsor that weekend
- Riot Slide Into Autumn 14u · New Paltz, NY · 19 mi · 14U · 13 teams
- The Rookie Rumble · Garfield, NJ · 41 mi · 14U · 38 teams
- Money Brawl · Medford, NYC · 51 mi · 14U · 3 teams
- ISLAND FASTPITCH INVITATIONAL 11th Annual Event · Hauppauge, NY · 62 mi · 10U, 12U, 14U, 16U, 18U · 51 teams
- Harvest Hits Fall League · Long Island, NY · 65 mi · 14U · 10 teams
- Halfmoon Fall Flash Invitational · Halfmoon, NY · 95 mi · 14U · 8 teams
Every softball tournament in New York that weekend, with field ratings
New York softball tournaments · Softball tournaments by region
Something wrong on this page? Tell us and we'll fix it. TourneyMagic is built by James Simmons, a softball parent in Austin, Texas. About.
Page updated Jun 20, 2026.