Fwiw i used to do huge horserides growing up in rural Australia in more recent times. It takes the region (or era) having support for it. There's literally horse tie-ups and grassy fields at the rest stops around Taree to support this. eg. The metal teepee's in the following street view next to the tables are for horses to tie them up as you take a break.

https://www.google.com/maps/place//@-31.9637446,152.4642729,...

If you zoom out on that link you'll see the entire area is cross-crossed by horse trails, they form a network for many hundreds of miles in every direction and everyone i knew growing up had a horse (they aren't that expensive if you have a paddock to feed them and with so many horses in the area the farrier/vets are relatively competitive).

Once a year during school holidays there was a horse jamboree (NSW pony club jamboree, still happening to this day) where you'd all make your way to one of the regions pony clubs with camping equipment (a different pony club hosted each year) for competition. They'd have routes planned out, camp sites assigned and stalls strung up with electric fence wire to keep your horse in. Some years we'd float (Australian term for using a horse trailer to get there) but other years could be a 100 mile multi-day ride.