Scenic challenging loop
This is a great, scenic loop starting and ending at the Roundup parking area, taking in several of the lesser used trails in the Santa Ritas. The usual way up Mt Wrightson is Old Baldy trail, which really just goes straight up and back down again. This makes the hike into a longer loop swinging to the northeast side of the mountains. See also the description for McCleary Peak Loop, which follows a similar (but not the same!) route. This hike starts and ends at the Roundup parking area and takes a roundabout route to the northeast to get to Mt Wrightson.
This is one of the more challenging routes in the Santa Ritas. All on trail, some unmaintained, often overgrown - route finding is sometimes needed.
I really like this route because it's mostly on lesser used trails, including a couple that are not on any maps I know of. All of the trails are used enough that it's usually easy to stay on them, but several do get very overgrown seasonally, so it's really useful to have the gps trace on hand.
From the Roundup parking area at the end of Madera Canyon Rd, head up the Super Trail at the lower end of the lot by the toilets. About 0.5 mi in there is an unsigned junction, turn left here to leave Super trail and head steeply up to a small saddle; this is the unofficial Pipeline trail. Continue steeply up the ridge line, following a well defined trail by the old water pipe line - hence the unofficial name of this trail. Pipeline intersects Kent Spring Trail (an old Jeep road) in a drainage, but instead of taking it, continue up the drainage following the unmaintained trail by the stream, which flows most of the year. I think this area is called Fern Canyon by locals, but is not marked on the maps as such. The trail crosses the stream a few times, then stays to the left of the water; about half a mile up it crosses and heads west over to Super trail. Just before this crossing there's a junction, turn sharp left to follow the contour around to Roger's Rock.
Stop on the rock to take in the views and some calories! From there the "trail" heads up the ridgeline very steeply for about 0.5 mi to connect with Four Springs trail. It can get somewhat overgrown here but the trail is used enough that it's not difficult to see. Continue uphill on Four Springs trail, which heads generally northeastward and up with several switchback sections, to Shovel Saddle in about 1.3m. From there if feels like you're curving around to the south but in fact the trail continues NE to an unnamed saddle by McCleary Peak in another 0.7 mi. There are some deadfall logs here that make good benches! From here Four Springs trail switchbacks down then follows the contour for about 0.7 mile, past Armor Spring (rusty metal sign) and and what I call Columbine Spring as there are sometimes masses of columbine flowers there, on to the junction with Crest Trail above Florida Saddle. Be warned that this last section of Four Springs trail gets very overgrown and can be hard to follow, and additionally crosses a steep slope so the footing can be bad. The junction with Crest trail is marked only by another rusty metal sign pointing back to Armor Spring. Crest trail heads up to Pine Saddle (about 0.7 mi again); note that you can bushwhack to Pine Saddle from Shovel Saddle, it's less than half a mile but steep and very uneven. From Pine Saddle stay on Crest trail all the way to Baldy Saddle, another 2.2m or so. There's a fair amount of up and some down, mostly at the end as you drop down to Baldy Saddle. From here you can wimp out and head back down Old Baldy trail, or zip up to Mt Wrightson peak (0.9 mi each way, about 650' AEG), well worth it for the 360 degree views and the sense of accomplishment!
From the peak its a long 5.5 mi downhill on Old Baldy trail via Baldy Saddle and Josephine Saddle back to the upper end of the Roundup parking area. If you want to add even more miles you can take Super Trail all the way down, I think that's more like 7.5 miles. You'll be happy to see the cars!
WARNING! Hiking and outdoor related sports can be dangerous. Be responsible and prepare for the trip. Study the area you are entering and plan accordingly. Dress for the current and unexpected weather changes. Take plenty of water. Never go alone. Make an itinerary with your plan(s), route(s), destination(s) and expected return time. Give your itinerary to trusted family and/or friends.