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First, don't bring a good map. Bring a cruddy little, general map of the park which spells out WHICH trails are horse accessible, and which are off limits, but omits super helpful info like, oh, topo details or, say, landmarks.
Then, don't bring a GPS. Newfangled technology makes outdoor adventures far too easy. You can't have a properly exhausting family adventure without losing yourself in a small maze of unofficial, but clearly well-established, trails.
Bring only one horse to be shared between four people. OK, we're technically three riders and one dedicated walker, but you get the idea.
Bring only the tack that accommodates the rider with the shortest legs.
Then set out before lunchtime knowing you have a good five hours before you have to load back into the trailer and head for home, and explore trail spurs along the way.
OK, certainly those aren't the ideal pointers, but that's what we had to work with and we had a fantastic day at Montana de Oro where Mr. B and I could never really be lost. The girls played along nicely and traveled well. Mattie performed wonderfullyl. We found a few sticky spots (she wasn't all that thrilled about stepping down over a thick root in a spot where she had to pass between a tall tree and a tall bank), but worked through them. V was onboard when Mattie decided to go UP the bank rather than simply walk past that "scary bank." Mr. B led Mattie across the first water hazard, which she preferred to jump. (HEAVEN forbid she should get her hooves wet.) She and I worked on that issue at a couple of other crossings, including a super challenging step from sticky mud, across a significant log into a running creek. I discovered she was just bluffing about that fear of water when she stopped mid-creek to graze.
While Mr. B and the girls began their return route, I took a short side canyon down to a fantastic stretch of beach before returning to the maze of trails in which we all spent a little extra time before calling it a day.
By the time we returned to the trailer, Mattie was a sweaty, muddy mess and we were all ready for naps. And I'm not sure any of us have fallen asleep so quickly at bedtime in recent history. I can hardly wait to do it again.