If you’re searching for a family-friendly Halloween event near Ventura County, Night of the Jack in Calabasas should be at the top of your list. My family has gone three years in a row, and it’s become a must-do tradition for us. From stroller-friendly trails and fun activities for kids to incredible pumpkin displays and festive cocktails for adults, it’s the perfect fall outing that truly has something for everyone.

Why It’s a Tradition for Us

Every October, my family looks forward to Night of the Jack. After three years of attending, I can say it’s the rare kind of Halloween event that manages to be magical for kids, relaxing for parents, and full of those little traditions that make memories stick.

The author received tickets to the event for this article. All thoughts and opinions expressed are her own.

A Stress-Free Evening for Parents

One of my favorite parts is that they offer an early “dusk” entry at 6 pm—perfect for younger kids. You can enjoy the magic while it’s still light out, snap your photos, and still get the little ones home and tucked into bed at a reasonable hour.

The trail itself is around a mile long and completely walkable. We’ve done it both with and without a stroller, and honestly, bringing one (or even a wagon) isn’t a bad idea if you’ve got tired legs in your group. The whole experience is fenced in and there is a rope border around the path to keep you on the trail.

Family Fun Along the Trail

What I love most is how interactive the experience is. Along the trail, you’ll find:

Virtual fall-themed games that kids can play at one stop.
Cut-outs and themed photo ops perfect for silly pictures.
A candy tent about halfway through where you can grab treats for purchase.
Light-up toys and glow sticks available at the entrance (fair warning to parents—your kids will notice them!).

Grown-Up Perks Too

Parents aren’t left out of the fun. Both at the entrance and halfway mark of the trail are bar stops called, The Spookeasy serving seasonal hot and cold craft cocktails, beer, and wine. It makes the walk feel festive for the whole family, and I’ll admit—themed cocktails always add to the magic for me.

An Apple Spiced Whiskey Cocktail at The Spookeasy

Why You Should Arrive Early

If you take my advice, plan to get there an hour before your timed entry. There’s so much to enjoy outside the trail:

Watch the professional pumpkin carver at work—it’s mesmerizing.
Grab a bite at one of the amazing food trucks (the variety is always impressive).
Take advantage of extra photo opportunities while you wait.
Just relax and soak up the family time before heading into the trail.

Final Thoughts: Worth the Drive

Coming from Ventura County, it’s absolutely worth the trip to Calabasas. Night of the Jack has the rare ability to be magical for kids while also giving parents little moments of enjoyment too. Between the incredible pumpkin displays, the thoughtful family touches (hello stroller-friendly trail), and the chance to make it a full evening out, it’s no surprise this event has become a non-negotiable family tradition for us.

If you are ready to buy your tickets, you can visit https://nightofthejack.com/