My experience with western saddles (the only thing I have ever ridden besides 2 rides in a jumper ) is not necessarily the brand name but the shape. Any brand can be good or bad it's subjective to the buyer/user/rider. Currently I ride a Circle Y barrel or reiner? I can't remember and I haven't used it in 2 months so off the top of my head I'm going to say reining since it's so durned heavy.
What you need to know is 'trail saddles' don't actually exist. If someone pushes a 'trail' saddle at you in a store laugh and walk away. Seriously. All it is is a new name for the lighter weight barrel saddles. LITERALLY. It'll have the same shape (maybe a shallower seat) and a round or circle skirt. Square skirts will always be your heavier models.
Barrel saddles - aside from the horn being 'taller' for supportive grabs (some not all) and the seat being 'deep' and 'tall' these are your lighter weight saddles. You'll be more likely to find them comfy for trails if you're unaccustomed to other types. They can be heavy and they're generally designed for short-term uses (making a run and then done) so be sure it's a full bar saddle otherwise you're in for a surprise on the trails!
Reiner/Cutting/Roping - from my experience these are really similar though not always. Usually your heavier 'fuller' saddles. The differences will be round or square seat, depth, and height of the seat. Thickness and height of the horn. Generally square skirted these may or may not be round-skirted as well. Circle skirts are unheard of (from my experience) as the skirt and weight of the saddle lends it self to the original use of western saddles which is to counter-act the weight of a cow (ropers) and hold in place correctly when the cow is tied to the saddle and the horse left to keep the slack out of the rope. Usually double-rigged these saddles will not fit correctly without the back cinch. They're designed to be held by both front and back cinches so if your horse has never had a back cinch stay away from these or get him/her properly desensitized to the back cinch!
Reiners (in general) have a lower front and a medium to low back. It both looks nice and keeps the saddle 'out of the way' of the riders hands. The low front enables the rider to keep their hands at the correct position(s) without struggle. Same can be said for saddles designed for WP (although most WP riders i've seen use reining saddles)
If you're looking to buy then write a list of what the saddle will be used for. Then write a list of what you LIKE in saddles. Go to a saddler ( an actual custom saddle maker ) and explain what you're looking for. He/She will be able to explain with examples and help you out and they're never shy about answering questions even if you don't buy with them!
Always make sure that full-padded seat is what you want. Some saddles come fully padded and that padding more often than not is the ONLY thing between the rider and the tree which means when that padding wears out it's time for the saddle to go. ( all trail saddles that stores will 'push' will be fully-padded and depending on how heavily used will need to be replaced within 5 years )
Endurance saddles - though generally not equipped with a horn - are a good route for pleasure trail riding. They're padded but not like 'trail saddles' and generally are light weight.
When it comes to saddles the more flash and tooling the higher the price. Those 'plain jane' untooled saddles or 'trimmed' saddles will always be the cheapest (even with brand names. inside that brand they're the cheapest!)
stay away from any out of country brands for western saddles as they're cheaply put together and usually use belly-skin leather which is the weakest leather on a cow.
definitely hit up a saddler! they can answer your questions better (and it's what I did and where I got my information).
SQUARE (typical) SKIRT
again all of what I said is JUST from my experience and what I can remember from the saddler and my shopping around