South Haven Halloween 2025: Pooch Parade & Headless Horseman

South Haven is gearing up for a season of Halloween fun, with a variety of beloved traditions returning throughout October. From costumed pups to a chilling ride at dusk, the city will be bustling with spooky excitement for the whole family.

Howl-O-Ween Pooch Parade

Kick things off Saturday, October 25, 2025, with Decadent Dogs’ annual Howl-O-Ween Pooch Parade. Guests are invited to gather at Dyckman Park at 2:50 p.m., with the parade starting at 3p.m.

Decadent Dogs via Facebook

Dogs and their humans are invited to strut in their best Halloween attire—whether it’s a themed family ensemble or a pup dressed as a pumpkin. A costume contest follows, with prizes for Best Dressed Dog and Best Dressed Family. Even if you don’t have a furry friend, spectators are welcome to line the route and cheer on the creativity.

👇BELOW: DISCOVER EVEN MORE HALLOWEEN FUN IN SOUTH HAVEN👇

The Headless Horseman Rides Again

As night begins to fall, the atmosphere in South Haven turns eerily magical. At 6:45 p.m., on Oct. 25, all eyes will be on Phoenix Street as the Headless Horseman makes his haunting ride through downtown. It’s a thrilling spectacle that has become a must-see tradition for families and Halloween fans alike.

Visit South Haven/ Decadent Dogs via Facebook

So grab your costumes, bundle up, and make your way to South Haven for a day filled with wagging tails, fall festivities, and one unforgettable encounter with the Headless Horseman.

Looking for more spooky fun in South Haven? Discover even more events coming up this fall:

Parades to the Headless Horseman: South Haven Halloween Fun 2025

South Haven is celebrating Halloween with fun events, from pumpkin carving and dog parades to spooky rides and festive carnivals. Enjoy seasonal fun throughout October, including the return of the legendary Headless Horseman and creative costume contests. Whether you’re attending with kids, pets, or friends, there’s something for everyone to get into the Halloween spirit.

8 Scenic Fall Chairlift Rides in Michigan

Soar high above Michigan's beautiful fall foliage!

Gallery Credit: Janna

30+ Photos That Show Why Fall in Michigan is Unmatched

Fall in the Mitten State is glorious time. There's apple picking, pumpkin carving, hayrides, all the animals you'll spot like deer and migratory birds—and of course the stunning fall colors.

The Upper Peninsula is often mentioned in national rankings as one of the most beautiful spots for fall foliage in the country, but truly, Autumn beauty abounds across the entire state.

Sure, we'd all love take a few hours and go on a scenic drive (or head to a fall chairlift ride) but sometimes you just can't getaway. Here are more than 30 photos of fall around Michigan for those times when you're stuck inside. Spot anywhere you've been?

Gallery Credit: Janna

Source: South Haven Halloween: Headless Horseman, Pooch Parade & More

Filed Under: Halloween, south haven

Categories: West Michigan News