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Rylie's Smile Thanksgiving 5K

  • Thompson Island Brewing Company 30133 Veterans Way Rehoboth Beach, DE, 19971 United States (map)

Rylie’s Smile Turkey Escape 5K at Thompson Island Brewing

Thanksgiving Morning – Thursday, November 26, 2026
Packet Pick-Up Celebration – Wednesday, November 25, 2026
📍 Thompson Island Brewing Company | 30133 Veterans Way, Rehoboth Beach, DE

Join us Thanksgiving morning at Thompson Island Brewing Company for the Rylie’s Smile Turkey Escape 5K, benefiting the Rylie’s Smile Foundation, a Delaware nonprofit supporting children with serious medical conditions.

Start your holiday with a great cause and a festive run through Rehoboth Beach. Enjoy community spirit, good times, and Thompson Island beer as we celebrate Rylie’s incredible mission to help families and children in need.


Packet Pick-Up Celebration

Wednesday, November 25 | 4:00–7:00 PM

Kick off Thanksgiving weekend early at Thompson Island with our Packet Pick-Up Celebration. Stop by to grab your race packet, enjoy live music from Catch The Drift, and get into the pre-race spirit with fellow runners and supporters.

The evening will also feature a silent auction, plus plenty of Thompson Island beer, food, and good times before race day.


Race Day

Thursday, November 26, 2026

Race Day Schedule

8:00 AM – Day-of registration and packet pick-up open
8:45 AM – Free Kiddie K for ages 9 and under
All Kiddie K participants receive a medal and goodies
9:00 AM – 5K and 1-Miler begin

Awards & Prizes

Overall winners, Masters winners, and the largest fundraising group will receive turkey-themed trophies and gift cards from The Lighthouse in Dewey Beach.

First-, second-, and third-place finishers in each age category will receive Turkey medals.

Turkey Costume Contest

Come dressed to impress for the annual Turkey Costume Contest. Judges Ernie Lopez and Pete Schwartzkopf will select the top three costumes, and each winner will take home a pie.

Post-Race Celebration

Race winners who cannot stay for the post-race party can pick up their Thanksgiving-themed trophies and medals at the Race Result Kiosk.

Post-race refreshments will be provided by Ladies Auxiliary #17, with complimentary beer and seltzers for guests 21 and over.


About Rylie’s Smile Foundation

Founded in 2015 by Rylie Maedler, the Rylie’s Smile Foundation is a 501(c)(3) nonprofit dedicated to helping families of children with severe or terminal medical diagnoses. The foundation provides monthly assistance to more than 75 families and advocates for safer, less-toxic treatment options for pediatric patients.

Learn more at RyliesSmileFoundation.org.

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November 25

Catch the Drift Live at Thompson Island

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November 27

The Gone Boys Live at Thompson Island Brewing