Halloween Weekend in South Haven: The Pooch Parade & Headless Horseman Returns

Posted by Emily Watson on 30th Sep 2026

Halloween Weekend in South Haven: The Pooch Parade & Headless Horseman Returns

Halloween weekend is almost here, and South Haven is getting ready for a little spooky fun! Whether you're bringing your four-legged friend downtown for the annual Pooch Parade or heading out to catch a glimpse of the Headless Horseman, there are two fun events you won't want to miss.

The Headless Horseman Rides Again

Friday, October 30 at 6:30 PM

As twilight falls over South Haven, keep your eyes on Phoenix Street. The Headless Horseman is rumored to be making his haunting return!

The ride is expected to take place around dusk, so gather your friends, bundle up, and line the sidewalks for a chance to catch a glimpse of this eerie Halloween tradition.

Will you be brave enough to watch him ride by?

Howl-O-Ween Pooch Parade

Saturday, October 31
Meet at 10:30 AM | Parade begins at 11:00 AM
Dyckman Park

What better way to celebrate Halloween than with a parade full of dogs in costume?

Bring your pup to Dyckman Park for the Howl-O-Ween Pooch Parade! We'll gather at 10:30 AM before stepping off at 11:00 AM for a fun walk through South Haven.

Of course, there will be plenty of costumes to see along the way, and the parade will include a costume contest with categories for Best Dressed Dog and Best Dressed Family.

And because no Halloween parade is complete without treats, Decadent Dogs will have goodie bags for participating families!

Whether your dog is going all-out with their costume or simply showing up in their favorite bandana, we'd love to see you there.

Make a Halloween Weekend of It

With the Headless Horseman riding Friday night and the Pooch Parade happening Saturday morning, it's a great weekend to get out and enjoy Halloween in downtown South Haven.

So grab your costume, bring your pup, and come enjoy a little spooky-season fun with us!

We'll see you downtown!

— Emily & the D-Dog Team