Illustration of flower, squirrel and bee with Bloomingdale Trail Run, 9/27/2025

Top 10 Reasons to Do the Bloomingdale Trail Run 

The 2025 Bloomingdale Trail Run is coming up on September 27. While the best reason to participate is the sheer joy of running with 750 fellow Trail-lovers while enjoying beautiful views, here are 10 more reasons you should register today! The last day to sign up (and guarantee a T-shirt!) is Tuesday, September 16!

10. The Music

Live music by Los Pleneros de Don Segundo! One of the city’s most sought-after Afro-Puerto Rican folkloric groups, performing original plena music.

9. Kids Run Free

Kids run free in the 1/4-mile and 1/2-mile dashes when you register with promo code FreeKid2025. Let’s be real, dozens of little ones dashing up the Trail is totes adorbs!

8. BOGO Burgers

The StopAlong is providing each runner with a Buy One Get One coupon. Run the Bloomingdale Trail and then head to The StopAlong at one of their two locations (2210 N California and 1812 N. Milwaukee) for a pizza or burger.

7. The Shirt

Every runner gets a Bloomingdale Trail Run T-shirt designed by local artist Kayce Bayer and featuring our beloved mascots Bloom (the purple coneflower), Dale (the squirrel), and Buzz (the honeybee).

6. The Churros

It wouldn’t be the Bloomingdale Trail run without Churros. Come hungry.

5. Caffeine

Coldbrew! Metropolis Coffee will be on hand to get your engines going.

4. Free Stuff

Fun samples to try – energy drinks, superfood gummies, custard and hydration tablets.

3. Bandannas

Live bandanna printing with Chicago Signs, which has been an incredible partner, printing all our shirts and totes for the life of the run.

2. Winners’ Circle

The fastest overall winners will receive gift certificates from Fleet Feet and Shake Shack among other prizes like Bloomingdale Trail honey!

And the Number One Reason to Register Today…

Bananas! Seriously, I can’t run without bananas.

Look Up! It’s the Bloomingdale Trail.

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