This ride is either a car shuttle, or a road ride at the end with "excess" downhill and climbing due to a closed road section that prevents the most direct connection.
Overflow parking can be found at the Sypes Canyon Trailhead, which is probably the best place to plan for parking; it's a short ride from there to the start of the trail.
There is almost no chance to prepare for the initial climb on Sypes Canyon Trail #531
. There is a short pedal through the trees and down to the first creek crossing, followed by a good climb up over steps in the trail, followed by a tough, rocky climb up to the first high point. If you can make it to here without stopping, you're in good shape!
There is a short downhill drop across a rocky section, then a short climb to a technical piece where the trail has eroded away over the years. After that, it's a nice ride through the trees, climbing back into the canyon and then back out to the first real overlook above the Gallatin Valley. A bench is found a little further up the trail where you can stop to take in the view.
The trail then switchbacks up along the ridge, with one notable loose, steep climb that typically ends in hike-a-bike fashion for 100 yards or so. A bit further along you come to the Crossroads—an intersection where the Bridger Foothills Trail #534
to the right (south) leads to the "M" (best route to takefor a "Sypes-M" connection), left to Middle Cottonwood, or straight on up (ENE) to the top of the ridge.
Turn around and head back down for a shorter trip to the car. The trail is frequented with many hikers and dogs, so it's important to pay attention and keep your speed under control!
To continue on, head left (north) on Bridger Foothills Trail #534
to go towards Middle Cottonwood Trail #586
. Sidehill across and down/up/down/etc. into the several small drainages between Sypes and Middle Cottonwood. There are some steep climbs along the way, occasionally taking the bike for a walk is the most convenient method of making uphill progress.
The downhill at the end into Middle Cottonwood is fast with numerous switchbacks and occasional fallen trees to watch out for. Middle Cottonwood Creek can be a fast-flowing one to cross—pick your route with care or you may end up with wet feet or worse!
The trail down crosses the creek several more times, and is rocky/technical in numerous sections. Take it easy, you're almost done!