A Chicago fall favorite is back on the water this October. First Lady’s Howl-O-Ween Canine Cruise is back October 17–18 and 24–25, bringing costumed pups and their humans to the Chicago Riverwalk. For the first time ever, First Lady is collaborating with One Tail at a Time, with adoptable dogs joining each cruise. Once aboard, guests will enjoy a 90-minute guided cruise along the Chicago River and Lake Michigan, pumpkin-flavored dog treats and a contest for the best-dressed dogs.  First Lady will enter costume contest winners into a drawing with the winner having a $1,000 donation made in their name to One Tail at a Time.

When: Saturday and Sunday, October 17–18 and 24–25; departure times vary

Where: First Lady Cruises, 112 E. Wacker Drive, Chicago, IL 60601

Tickets: Starting at $46 for general boarding

For more information, visit firstlady.com

Photo Credit: First Lady