The Milligan
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The Milligan


Watertown, Tennessee


The Most Beautiful Bicycle Ride in Middle TN!

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Get Ready for the The Milligan!

Get Ready for the The Milligan!

The Big Hill Challenge is now The Milligan.

It is our honor to bring you The Milligan (formerly known as The Big Hill Challenge) and to share who our fellow cyclist and friend was.

In 2023 the cycling community, friends and family lost Alyssa Milligan when she was killed by a motorist while riding on Hwy. 100 in Nashville, TN. Alyssa loved God and she was a reflection of God’s love to all she encountered. She had a huge smile and an easy way. If you met her, you were her friend. Alyssa was an avid and skilled cyclist who easily and naturally brought cyclists together. It is because of this very special gift of hers that The Milligan is now a signature event that portrays the community, family and strength of how Alyssa lived her life.

We cannot bring her back, but we can keep her in our hearts and minds as we advocate for safer streets. The Milligan will celebrate Alyssa and provide a means to advocate for safer streets through the proceeds. Join us in remembering Alyssa’s contagious smile, passion for cycling, and desire to bring people together.

The 20th annual ride is June 8th, 2024 in Watertown, TN. The most beautiful ride in Middle Tennessee, The Milligan begins and ends in Watertown, TN., nestled just outside of Nashville. Watertown and the surrounding countryside combine breathtaking scenery and challenging terrain to create the perfect spot for an unforgettable cycling adventure.

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