Windham Little League

08/14/2026

Windham Little League juniors softball ousts Portland in championship game
https://sports.thewindhameagle.com/2026/08/windham-little-league-juniors-softball.html
Windham Little League

08/14/2026

Juniors baseball wins Windham Little League division title
https://sports.thewindhameagle.com/2026/08/juniors-baseball-wins-windham-little.html
Windham Little League

08/06/2026

08/01/2026

⚾️ Reminder! Fall Baseball & Softball Registration Closes TODAY – August 1! ⚾️

Don't miss your chance to play this fall with Windham Little League!

Registration closes today, August 1, so we can begin forming teams and ordering uniforms. Once registration closes, we'll be putting together rosters and placing uniform orders, so late registrations may not be accepted.

If you haven't signed up yet, please register today to guarantee your player's spot.

We can't wait to see everyone back on the field for another great season of baseball and softball!

🍂⚾ Register now before it's too late!

07/18/2026

⚾️🦅 COME OUT AND SUPPORT YOUR WINDHAM EAGLES! 🦅⚾️

The Windham Eagles Juniors are beginning their playoff run, and they need your support!

⚾️ Game 1 – Away
📅 Monday, July 20
🕠 5:45 PM
📍 Tri-Town

⚾️ Game 2 – Home
📅 Friday, July 24
🕠 5:45 PM
📍 vs. Westbrook Blue Blazes

🏆 If the Eagles win both games, they’ll advance to the Championship Game on Wednesday, July 29, at home!

Let’s pack the stands, cheer them on, and make some noise!

📣 Show up. Be loud. Wear your maroon.

💪 One Goal. One Team. Let’s Bring It Home! 🦅⚾️

07/17/2026

🎉 Congratulations to All of Our 2026 Windham Little League Calendar Raffle Winners! 🎉

Congratulations to all of our 2026 Calendar Raffle winners! We sincerely appreciate everyone who participated and supported Windham Little League throughout this year's raffle.

🏆 2026 Calendar Raffle Winners:

Day 1: Andy Allen – $50 Aroma Joe's Gift Card ☕
Day 2: Ben Townsend – $25 Pat's Pizza Gift Card 🍕
Day 3: Jonathan Day – $25 Fire & Ice Maine Gift Card 🔥
Day 4: Jessica Talbot – $25 Red City Ale House Gift Card 🍽️
Day 5: Kim Allen – $50 Rose's Italian Restaurant Gift Card 🍝
Day 6: Spencer Houlette – $25 Target Gift Card 🎯
Day 7: Andrea Raynor – $25 Dunkin' Gift Card ☕🍩
Day 8: Patricia Diehlmann – $25 Hannaford Supermarkets Gift Card 🛒
Day 9: Edward Roberts – $25 Windham Smoked Gift Card 🥩
Day 10: Matt Vanderburgh – $25 Starbucks Gift Card ☕
Day 11: Erin Haley – $25 Luchador Tacos Gift Card 🌮
Day 12: Sophie Oliveri – $25 Erik's Church Gift Card 🎶
Day 13: Peter Brichetto – $25 Dick's Sporting Goods Gift Card 🏅
Day 14: Cindy Croxford – $25 Stockhouse Restaurant & Pub Gift Card 🍽️
🏆 Day 15 Grand Prize: Louie Olsen – $500 Hannaford Supermarkets Gift Card! 🛒💵
Day 16: Moon Construction – $25 Chipotle Gift Card 🌯
Day 17: Heidi Young – Congratulations! 🎉
Day 18: Lisa Ross – $25 Lake House Tavern Gift Card 🍽️
Day 19: Allen Mancini – $25 Irving Gas Card ⛽
Day 20: Kendra Graves – $50 Aroma Joe's Gift Card ☕
Day 21: Ashley Berry – $25 Ice Cream Dugout Gift Card 🍦
Day 22: Bill Bulger – $25 Beacon Pizza Gift Card 🍕
Day 23: Deb Roy – $25 Amazon Gift Card 🎁
Day 24: Kim Cullen – $25 Corsetti's Windham Gift Card 🛒
Day 25: Martha Vance – $25 Dairy Queen Gift Card 🍦
Day 26: Kaullen Winter – $25 McDonald's Gift Card 🍟
Day 27: Kathy Skillin – $25 Walmart Gift Card 🛍️
Day 28: Carrie Fortino – $25 Double Play Collectibles Gift Card ⚾
Day 29: Jana Merrill – $25 Crow's Nest Barbershop Gift Card 💈
Day 30: Tom Wilson – $100 Rustler's Steakhouse Gift Card 🥩

Tim Gaudet will be reaching out to all winners shortly to arrange prize pickup. Please be patient as we work through contacting everyone.

If you have any questions or would like to claim your prize sooner, please feel free to contact Tim Gaudet at 207-939-6235.

A heartfelt thank you to everyone who purchased raffle tickets and supported Windham Little League. Your generosity helps provide a fun, safe, and memorable baseball and softball experience for hundreds of local players each season.

⚾ Congratulations once again to all of our winners, and thank you for making the 2026 Windham Little League Calendar Raffle a tremendous success! We couldn't do it without the incredible support of our players, families, sponsors, and community. See you at the ballpark! ❤️

07/16/2026

🎉 2026 Windham Little League Raffle – Day 30 Winner! 🎉

Congratulations to Tom Wilson! 🎊

Tom is our Day 30 raffle winner and has won a $100 Rustler's Steakhouse Gift Card! 🥩🎁

Congratulations, Tom, and thank you for participating in and supporting Windham Little League!

🏆 2026 Raffle Winners (So Far):

Day 1: Andy Allen – $50 Aroma Joe's Gift Card ☕
Day 2: Ben Townsend – $25 Pat's Pizza Gift Card 🍕
Day 3: Jonathan Day – $25 Fire & Ice Maine Gift Card 🔥
Day 4: Jessica Talbot – $25 Red City Ale House Gift Card 🍽️
Day 5: Kim Allen – $50 Rose's Italian Restaurant Gift Card 🍝
Day 6: Spencer Houlette – $25 Target Gift Card 🎯
Day 7: Andrea Raynor – $25 Dunkin' Gift Card ☕🍩
Day 8: Patricia Diehlmann – $25 Hannaford Supermarkets Gift Card 🛒
Day 9: Edward Roberts – $25 Windham Smoked Gift Card 🥩
Day 10: Matt Vanderburgh – $25 Starbucks Gift Card ☕
Day 11: Erin Haley – $25 Luchador Tacos Gift Card 🌮
Day 12: Sophie Oliveri – $25 Erik's Church Gift Card 🎶
Day 13: Peter Brichetto – $25 Dick's Sporting Goods Gift Card 🏅
Day 14: Cindy Croxford – $25 Stockhouse Restaurant & Pub Gift Card 🍽️
🏆 Day 15 Grand Prize: Louie Olsen – $500 Hannaford Supermarkets Gift Card! 🛒💵
Day 16: Moon Construction – $25 Chipotle Gift Card 🌯
Day 17: Heidi Young – Congratulations! 🎉
Day 18: Lisa Ross – $25 Lake House Tavern Gift Card 🍽️
Day 19: Allen Mancini – $25 Irving Gas Card ⛽
Day 20: Kendra Graves – $50 Aroma Joe's Gift Card ☕
Day 21: Ashley Berry – $25 Ice Cream Dugout Gift Card 🍦
Day 22: Bill Bulger – $25 Beacon Pizza Gift Card 🍕
Day 23: Deb Roy – $25 Amazon Gift Card 🎁
Day 24: Kim Cullen – $25 Corsetti's Windham Gift Card 🛒
Day 25: Martha Vance – $25 Dairy Queen Gift Card 🍦
Day 26: Kaullen Winter – $25 McDonald's Gift Card 🍟
Day 27: Kathy Skillin – $25 Walmart Gift Card 🛍️
Day 28: Carrie Fortino – $25 Double Play Collectibles Gift Card ⚾
Day 29: Jana Merrill – $25 Crow's Nest Barbershop Gift Card 💈
Day 30: Tom Wilson – $100 Rustler's Steakhouse Gift Card! 🥩

A huge thank you to everyone who purchased raffle tickets and continues to support Windham Little League. Your generosity helps provide opportunities for hundreds of local players each season and keeps our league thriving.

Congratulations to all of our 2026 Calendar Raffle winners, and thank you again for supporting Windham Little League! ⚾❤️

07/16/2026

🎉 2026 Windham Little League Raffle – Day 29 Winner! 🎉

Congratulations to Jana Merrill! 🎊

Jana is our Day 29 raffle winner and has won a $25 Crow's Nest Barbershop Gift Card! 💈🎁

Congratulations, Jana, and thank you for participating in and supporting Windham Little League!

🏆 2026 Raffle Winners (So Far):

Day 1: Andy Allen – $50 Aroma Joe's Gift Card ☕
Day 2: Ben Townsend – $25 Pat's Pizza Gift Card 🍕
Day 3: Jonathan Day – $25 Fire & Ice Maine Gift Card 🔥
Day 4: Jessica Talbot – $25 Red City Ale House Gift Card 🍽️
Day 5: Kim Allen – $50 Rose's Italian Restaurant Gift Card 🍝
Day 6: Spencer Houlette – $25 Target Gift Card 🎯
Day 7: Andrea Raynor – $25 Dunkin' Gift Card ☕🍩
Day 8: Patricia Diehlmann – $25 Hannaford Supermarkets Gift Card 🛒
Day 9: Edward Roberts – $25 Windham Smoked Gift Card 🥩
Day 10: Matt Vanderburgh – $25 Starbucks Gift Card ☕
Day 11: Erin Haley – $25 Luchador Tacos Gift Card 🌮
Day 12: Sophie Oliveri – $25 Erik's Church Gift Card 🎶
Day 13: Peter Brichetto – $25 Dick's Sporting Goods Gift Card 🏅
Day 14: Cindy Croxford – $25 Stockhouse Restaurant & Pub Gift Card 🍽️
🏆 Day 15 Grand Prize: Louie Olsen – $500 Hannaford Supermarkets Gift Card! 🛒💵
Day 16: Moon Construction – $25 Chipotle Gift Card 🌯
Day 17: Heidi Young – Congratulations! 🎉
Day 18: Lisa Ross – $25 Lake House Tavern Gift Card 🍽️
Day 19: Allen Mancini – $25 Irving Gas Card ⛽
Day 20: Kendra Graves – $50 Aroma Joe's Gift Card ☕
Day 21: Ashley Berry – $25 Ice Cream Dugout Gift Card 🍦
Day 22: Bill Bulger – $25 Beacon Pizza Gift Card 🍕
Day 23: Deb Roy – $25 Amazon Gift Card 🎁
Day 24: Kim Cullen – $25 Corsetti's Windham Gift Card 🛒
Day 25: Martha Vance – $25 Dairy Queen Gift Card 🍦
Day 26: Kaullen Winter – $25 McDonald's Gift Card 🍟
Day 27: Kathy Skillin – $25 Walmart Gift Card 🛍️
Day 28: Carrie Fortino – $25 Double Play Collectibles Gift Card ⚾
Day 29: Jana Merrill – $25 Crow's Nest Barbershop Gift Card 💈

A huge thank you to everyone who purchased raffle tickets and continues to support Windham Little League. Your generosity helps provide opportunities for hundreds of local players each season and keeps our league thriving.

Stay tuned as we continue announcing more raffle winners. Good luck to everyone still in the drawing! ⚾🎟️

07/16/2026

🎉 2026 Windham Little League Raffle – Day 28 Winner! 🎉

Congratulations to Carrie Fortino! 🎊

Carrie is our Day 28 raffle winner and has won a $25 Double Play Collectibles Gift Card! ⚾🎁

Congratulations, Carrie, and thank you for participating in and supporting Windham Little League!

🏆 2026 Raffle Winners (So Far):

Day 1: Andy Allen – $50 Aroma Joe's Gift Card ☕
Day 2: Ben Townsend – $25 Pat's Pizza Gift Card 🍕
Day 3: Jonathan Day – $25 Fire & Ice Maine Gift Card 🔥
Day 4: Jessica Talbot – $25 Red City Ale House Gift Card 🍽️
Day 5: Kim Allen – $50 Rose's Italian Restaurant Gift Card 🍝
Day 6: Spencer Houlette – $25 Target Gift Card 🎯
Day 7: Andrea Raynor – $25 Dunkin' Gift Card ☕🍩
Day 8: Patricia Diehlmann – $25 Hannaford Supermarkets Gift Card 🛒
Day 9: Edward Roberts – $25 Windham Smoked Gift Card 🥩
Day 10: Matt Vanderburgh – $25 Starbucks Gift Card ☕
Day 11: Erin Haley – $25 Luchador Tacos Gift Card 🌮
Day 12: Sophie Oliveri – $25 Erik's Church Gift Card 🎶
Day 13: Peter Brichetto – $25 Dick's Sporting Goods Gift Card 🏅
Day 14: Cindy Croxford – $25 Stockhouse Restaurant & Pub Gift Card 🍽️
🏆 Day 15 Grand Prize: Louie Olsen – $500 Hannaford Supermarkets Gift Card! 🛒💵
Day 16: Moon Construction – $25 Chipotle Gift Card 🌯
Day 17: Heidi Young – Congratulations! 🎉
Day 18: Lisa Ross – $25 Lake House Tavern Gift Card 🍽️
Day 19: Allen Mancini – $25 Irving Gas Card ⛽
Day 20: Kendra Graves – $50 Aroma Joe's Gift Card ☕
Day 21: Ashley Berry – $25 Ice Cream Dugout Gift Card 🍦
Day 22: Bill Bulger – $25 Beacon Pizza Gift Card 🍕
Day 23: Deb Roy – $25 Amazon Gift Card 🎁
Day 24: Kim Cullen – $25 Corsetti's Windham Gift Card 🛒
Day 25: Martha Vance – $25 Dairy Queen Gift Card 🍦
Day 26: Kaullen Winter – $25 McDonald's Gift Card 🍟
Day 27: Kathy Skillin – $25 Walmart Gift Card 🛍️
Day 28: Carrie Fortino – $25 Double Play Collectibles Gift Card ⚾

A huge thank you to everyone who purchased raffle tickets and continues to support Windham Little League. Your generosity helps provide opportunities for hundreds of local players each season and keeps our league thriving.

Stay tuned as we continue announcing more raffle winners. Good luck to everyone still in the drawing! ⚾🎟️