The Richard T Brennan Fair Winds Memorial Foundation

10/10/2026

Two weeks to go, and there's still time to register!

Online registration open until Tuesday, 10/20, day of registration available but must arrive 20 min prior to race start (10am).

Register here now to guarantee your race shirt.

The RTB Fair Winds 5k/Fun Run is on Saturday October 24, 2026. It includes the following events: 4th Annual 5K/Fun Run and RTB Fair Winds Virtual 5k/Fun Run.

10/04/2026

EARLY BIRD PRICING ENDS AT MIDNIGHT TONIGHT!

Plan to join us at the 4th Annual RTB Fair Winds 5k/Fun Run? Get registered today and enjoy $10 off adult registration and guarantee your race shirt. All student rates remain until race day.

Come in costume, or not. Run, walk, jog, cheer, volunteer. Just come on down for a morning of community and support for the work our foundation does to support future leaders!

October 24th
10am - start
Quiet Waters Park, Annapolis, MD

The RTB Fair Winds 5k/Fun Run is on Saturday October 24, 2026. It includes the following events: 4th Annual 5K/Fun Run and RTB Fair Winds Virtual 5k/Fun Run.

09/27/2026

🍂🏃‍♀️ Fall Fun + Early Bird Savings! 🏃‍♂️🍂

Looking for a fun way to get outside, enjoy the fall weather, and support a great cause? We’ve got you covered!

The 4th Annual RTB Fair Winds 5K/Fun Run is coming up, and now is the perfect time to register and save! 🍁

📅 Saturday, October 24, 2026
📍 Quiet Waters Park, Annapolis, MD
⏰ 10:00 AM Start
🏃 5K or 1-Mile Fun Run

🍂 EARLY BIRD PRICING ENDS OCTOBER 4TH! 🍂
$35 – Register by October 4th
$45 – October 5th through race day
Special student pricing continues!

Race shirts are included with registration while supplies last! Pre-register by October 20th to guarantee your shirt.

Whether you’re running, walking, bringing the family, or cheering from the sidelines, this is a great opportunity to enjoy a fall morning with friends, family, and our amazing community. Costumes are optional, and we’ll have prizes for best costume to add a little extra fall fun! 🎃👻

Every registration supports RTB Fair Winds' mission, helping us honor Rick’s legacy through scholarships, grief camp opportunities for children, and blood donation advocacy.

🍁 Don’t wait—register by October 4th to take advantage of early bird pricing!

👉 Sign up here:
https://runsignup.com/Race/MD/Annapolis/RTBFairWinds5kFunRun

Tag your running buddies, walking partners, and anyone who loves a good fall outing! 🍂❤️

The RTB Fair Winds 5k/Fun Run is on Saturday October 24, 2026. It includes the following events: 4th Annual 5K/Fun Run and RTB Fair Winds Virtual 5k/Fun Run.

09/21/2026

Check that item off your list with early bird pricing until Oct 4th! Registration link in the comments. Costumes are optional but encouraged!

09/12/2026

SIX WEEKS TO GO!!

Join us for the 4th Annual RTB Fair Winds 5K/Fun Run!
📅 Saturday, October 24, 2026
⏰ 10:00 AM
📍 Quiet Waters Park | Annapolis, MD
Whether you’re a serious runner, a casual walker, or just looking for a fun family morning, there’s a course for everyone! Choose the 5K or our 1-mile course and come out to enjoy a great morning with family and friends.
Registration:
• $35 Early Bird through October 4
• $45 October 5 through race day
• $15 Youth (14 & under)
• $25 Ages 15–22
Race shirts included while supplies last!

🎃 COSTUMES ARE ENCOURAGED! 🎃
Come dressed to have some fun! We’ll be awarding prizes for the best group/family-themed costumes and the best individual youth and adult costumes. And we have more fun planned, so stay tuned as race day gets closer!
🙋‍♀️
VOLUNTEERS!
Not a runner but want to participate? We’re looking for volunteers to help make race day a success. If you’d like to lend a hand, cheer on the participants, and be part of the RTB Fair Winds team, we’d love to have you! Reach out to Tracey at [email protected] to volunteer.

Can’t make it to Annapolis but still want to support RTB Fair Winds? You can join virtually or become a race sponsor. Sponsorship opportunities are available through the registration site, or reach out to Tracey for more information.

Every registration, donation, and volunteer hour helps us continue the work of RTB Fair Winds in Rick’s memory of supporting future leaders, helping children heal from traumatic loss, and giving back to our community.

👉 REGISTER HERE:
https://runsignup.com/Race/MD/Annapolis/RTBFairWinds5kFunRun
Grab your family, friends, running buddies and your costumes and join us! We can’t wait to see you at the starting line! ⚓️💙

The RTB Fair Winds 5k/Fun Run is on Saturday October 24, 2026. It includes the following events: 4th Annual 5K/Fun Run and RTB Fair Winds Virtual 5k/Fun Run.

09/02/2026

Big Thank YOU to our race course sponsor, Blake Sibley, The Citadel Class of 1990. We appreciate you and your support!

And, thank you to all who have registered, sponsored and are sharing our event. We are looking to have a great turnout and lots of FUN! Watch this space for more details.

4th Annual RTB Fair Winds 5k/Fun Run
Saturday, October 24, 2026
Quiet Waters Park, Annapolis

Volunteer spots are still open and we would love some help. Interested? Email Tracey at [email protected].

Looking to participate? Register here:

The RTB Fair Winds 5k/Fun Run is on Saturday October 24, 2026. It includes the following events: 4th Annual 5K/Fun Run and RTB Fair Winds Virtual 5k/Fun Run.

08/24/2026

Have you seen our cool new race shirt? Want one?

Join us on Saturday, October 24th, 10am for the 4th Annual RTB Fair Winds 5k/Fun Run. Shirt included with registration while supplies last and sponsors are proudly displayed on the back.

Costumes encouraged - prizes, fun, comraderie and a bit of competititiveness. Fun for the whole family

https://runsignup.com/Race/MD/Annapolis/RTBFairWinds5kFunRun

08/23/2026

🎉 Registration is OPEN! 🎉

Join us for the 4th Annual RTB Fair Winds 5K/Fun Run!

📅 Saturday, October 24, 2026
⏰ 10:00 AM
📍 Quiet Waters Park | Annapolis, MD

Whether you’re a serious runner, a casual walker, or just looking for a fun family morning, there’s a course for everyone! Choose the 5K or our 1-mile course and come out to enjoy a great morning with family and friends.

Registration:
• $35 Early Bird through October 4
• $45 October 5 through race day
• $15 Youth (14 & under)
• $25 Ages 15–22
👕 Race shirts included while supplies last!

🎃 COSTUMES ARE ENCOURAGED! 🎃
Come dressed to have some fun! We’ll be awarding prizes for the best group/family-themed costumes and the best individual youth and adult costumes. And we have more fun planned, so stay tuned as race day gets closer!

🙋‍♀️ WE NEED VOLUNTEERS!
Not a runner? No problem! We’re looking for volunteers to help make race day a success. If you’d like to lend a hand, cheer on the participants, and be part of the RTB Fair Winds team, we’d love to have you! Reach out to Tracey at [email protected] to volunteer.

Can’t make it to Annapolis but still want to support RTB Fair Winds? You can join virtually or become a race sponsor. Sponsorship opportunities are available through the registration site, or reach out to Tracey for more information.
Every registration, donation, and volunteer hour helps us continue the work of RTB Fair Winds in Rick’s memory—supporting future leaders, helping children heal from traumatic loss, and giving back to our community.

👉 REGISTER HERE:
https://runsignup.com/Race/MD/Annapolis/RTBFairWinds5kFunRun

Grab your family, friends, running buddies and your costumes and join us! We can’t wait to see you at the starting line! ⚓️💙

The RTB Fair Winds 5k/Fun Run is on Saturday October 24, 2026. It includes the following events: 4th Annual 5K/Fun Run and RTB Fair Winds Virtual 5k/Fun Run.

08/15/2026

Remembering Rick today on his 58th birthday! Birthday cake is great, but he loved a good key lime pie.

He is missed dearly everyday, but through the foundation, we keep his memory and legacy of thoughtful leadership and mentorship alive. Cheers to Rick and all the good he created.