Mark from Saint Louis, MO 63144 on 2/15/2026 4:57:20 PM:
Personally, I think North to South (Deadwood to Edgemont) is the way to go. The last 45 miles from Custer to Edgemont is virtually downhill - not flat, but downhill for sure. If you start with those 45 miles going uphill to Custer, it takes more work. IMO.
If you start in Deadwood, it's 48 miles or so to Hill City, the highest point of the trail at 5,000 feet. The first 16 miles and the last 7 into Hill City are uphill, but the other 25 miles are downhill. That's assuming you want to do the trail in two days. That does leave you 60 miles from Hill City to Edgemont on day 2, but mostly downhill. If you could go another 16 miles on day 1, you could make it to Custer leaving you only 44 miles to finish on day 2.
There are several nice hotels in Hill City and it's a nice town to stay in. We usually stay at the Comfort Inn & Suites on Old Hill City Road, but there are other nice hotels to select from. I'm not familiar with the hotels in Custer, but there are some there. Holiday Inn Express, Comfort Inn, etc.
I've never tried to break up the ride into 3 or 4 days, so I'm not sure where I'd stay if I broke up the miles that way. I am partial to an overnight in Hill City due to the good restaurants there.
I always take my own bike, so I can't help you with the bike rentals.
I've never used the shuttle services, but there are many you can find with a quick Google search. Here's one: https://www.touringintheblackhills.com/
Good luck.
This is a good elevation and distance map of the trail showing you the Mile Posts and what is at each one. You can see the (mostly) downhill section from Custer to Edgemont if you are going southbound.
https://www.scribd.com/document/92691828/Mickelson-Trail-Guide