Let's start with the Pueblo to Springs route:
1. Jerry Murphy Road out of Pueblo is good road out to Overton Road. It changes to relatively smooth dirt but can be a bit sandy north of there. It stays dirt until Hannover Rd at around mile 26. From there the road would be a very pleasant...read: quite
...road all the way to Fountain. Right outside of Fountain, it's even rather pretty.
2. In Fountain, you get on Santa Fe Ave which is fairly busy. You don't have to do that. I think you can continue further north on the
dirt path to the Springs. I've not done this section (I have ridden north from the El Pamor Sports complex) but you can see the trail from I-25 and it looks pretty complete. Turn left on Lyckman Dr (about 1/4 mile north of your 37 mile marker) just north of Fountain to access the trail. This trail should tie into the one that you are taking all the way through Co Springs.
3. Not sure why you are taking the detour off the Santa Fe Trail at the Air Academy. Is that where you are staying for the night? If so, you could probably find a hotel in the Springs that is more on your route or you could adjust your route to the east of I-25 so that you don't have to back track so much. That's a 3 mile detour. You could go up Woodman Rd in the Springs and catch Academy Blvd(CO 83 which isn't the best riding in town but you'd only be on it for a few miles)
Co Springs to Denver
I'm not timid nor do I scare easily but I, personally, wouldn't ride CO83. It's rather narrow and has lots of traffic. It doesn't make for the most pleasant of riding. Better to realign yourself with the Santa Fe Trail through the Air Academy and on up to Palmer Lake. Out of Palmer Lake take either 105 (Perry Park Road) to Sedalia or take 18 to Larkspur.
1. 105/Perry Park isn't too bad (again like CO83 it's narrow with lots of traffic) but it does place you on US 85 to continue into Denver. If you go that route, I'd get on Plum St in Sedalia and follow it to Airport Road. Then just suck it up and ride US85. US85 is narrow in this area but doable. Once you get to Titan Rd, it widens out and has good shoulders all the way to C-470. At C-470, get on to the bike path (you'll turn left just before the highway...probably outta use the cross walk) and go west to the first right turn. This is the start of the Platte River Green way. You can take it north.
2. CO18 to Larkspur has a short (about a mile) section of riding on I-25 which isn't as bad as it sounds
followed by several miles of frontage road to Castle Rock. The frontage road on the east side of I-25 turns into Wilcox St. which is kind of the main drag through Castle Rock. At Fifth St. (the bottom of the castle of Castle Rock) , you have some choices to make. If you turn right on 5th, you can go up and over the hill behind the castle and over to Franktown then north to Denver on your original route.
You can also go up the road a ways and watch for Founder's Parkway. Take Founder's north to Ridge Rd and then follow Ridge to Crowfoot Valley Road. Crowfoot Valley Road ends at Stroh Road (it turns into Motsenbrocker Road). Turn right on Stroh Road and you'll be able to pick up the Cherry Creek Path there. I haven't ridden Crowfoot Valley Rd but it looks intriguing on the map.
This entire route will involve lots of dirt riding. That zaps your energy so be aware. If you want less dirt, follow the frontage roads along I-25 (and some I-25 riding
). It's noisier but it's not unsafe.