Beginning at Matthews Winters Park, follow the Red Rocks Trail across the small stream and a bridge by the bathrooms. You'll go up a small hill and then experience rolling hills through Cherry Gulch Trail until you get to the Morrison Slide Trail, where you begin your first decent-sized climb.
Enjoy the view at the top of Morrison Slide Trail as you look east to Dakota Ridge Trail, where you'll be finishing the run. Following Morrison Slide Trail back down to the Red Rocks Trail, you'll take this to the road. Upon hitting the road, take a right and run alongside the road for a short while. Take your next right up Plains View Road and you'll quickly see the Geologic Connector begin on the left.
Follow this trail up to the picnic area and continue past the bathroom to join the Geologic Overlook Trail where a steep climb begins—be ready for lots of steps. Upon hitting the apex and descending, the road appears once more. Hang a right and run into the Amphitheater itself. Take a few laps along the famous rows or simply head down the steps. You'll want to exit to the right of the stage and from here, keep an eye out for signs to the Trading Post—this is where the Trading Post Loop begins.
Upon finishing Trading Post, hop across the road, directly across from the Trading Post building, to find the Will Call Trail. Follow this trail northeast, cross the park road, and continue on the trail as it heads east. This singletrack will bring you close to Hwy-93 that runs alongside Dakota Ridge Trail. You'll see signs for the Mount Vernon Creek Trail. When you've nearly reached the road, you'll have the option to take a left or right on the Mount Vernon Creek Trail—take a left.
You'll end up at a small parking lot, at which you can see the exit to the main road. Cross the road and you'll see signs for the Red Rocks Trail and Dakota Ridge Trail. Continue along Red Rocks Trail which will guide you to Dakota Ridge Trail.
After the trail spits you out on the road once more, you want to continue down the hill to the right, along Dinosaur Ridge. You'll see a port-a-jon, which is where Dakota Ridge Trail picks back up. From here, you've got the toughest climb of the day–a series of about five hills. It's tough going, but you'll be rewarded with some killer views of Red Rocks to the west and Denver to the east. Dakota Ridge Trail will guide you all the way back to the Matthews Winters parking lot.