Can you do it? Yes, you can. But speaking the local languages and/or Russian really, really helps. Instructions for the trip in reverse at the bottom.
Realistically, you should break up the trip by doing an overnight in Khujand. If you want to just get to Osh, here's how to do it:
When leaving Dushanbe, start from the Cement Factory (Tsement zavod) car station. I started here at 8:30am and I went with a driver who was going to Isfara. You should ignore all the other drivers. Only go with a driver who calls out "Isfara" or "Konibodom." Don't call out Isfara yourself or one of the cheating liar types will then make you a ridiculous offer, or worse you will be taken by a Khujand or Istarafshan driver who will then try to sell you to an Isfara driver at Khujand (that will take forever).
Luckily, I found a driver who already had three passengers. I left within 2 minutes of arriving at the Cement Factor. This is where language skills (or luck) helps you. If you end up waiting 2 hours for a car to fill up, you won't make it to Osh.
I agreed to the price of 150 Somoni. My fellow passengers paid 130, but they were dropped off in Konibodom. So, basically, the price for a seat in a decent car to Isfara at the local price is 140 Somoni.
My driver went as far as Konibodom, and then "sold" me to a driver who was doing the last short drive to Isfara. This is not a problem as there are regular departures between these two towns, and the driver had already called ahead for a driver who was ready and waiting.
I arrived in Isfara at 2:20pm, and that includes 40 minutes wasted at various stops along the way.
This is where it gets complicated. To get from Isfara to the border (and onwards) you have many options from the Isfara vokzal.
1. Your driver may offer to take you onward to the border for a price.
2. A seat in a shared car for 7 Somoni (not recommended, too slow to fill up)
3. Get on the #247 marshrutka (mini-bus) "Isfara-Guliston" that ends at the border for 2 Somoni (a good option with regular departures)
4. Talk to one of the drivers with Kyrgyz plates/license who is going al the way to Osh. This is where you need to be careful. This is a good option in that you no longer have to worry about any other transfers, but it takes forever to fill up a car.
I took option number 4 and waited for 1 hour and 40 minutes for the car to fill up. I eventually gave up and started to talk to other drivers (again, this is where language skills come in handy). I found a guy who said he was ready to leave, but that he had a complicated offer. He would take me in a local taxi to the border where his car was waiting in between the two border crossings. He would then drive me across the Kyrgyz side and "sell" me to his ready and waiting friend who would take me to Osh. I really needed to go (I was running out of time) and my visa was expiring same day. He asked 180 Somoni, but we agreed to 150 Tajik Somoni for the full trip from the Isfara station to central Osh. I think the local price would be about 500-600 Kyrgyz Som.
The border took 45 minutes, and we wasted 15 minutes in Batken exchanging money. We left central Batken at 5pm and arrived in Osh at 9pm (Dushanbe time).
If everything goes perfectly, you could do this trip in 11 hours. But it probably won't. Be warned that late in the day very few people are going to Osh from Batken. The last marshrutka leaves at 2pm. At 5pm our driver couldn't find anybody for the last seat in his car, and so he gave up and left without a final passenger. Nobody was at the Batken bus station looking to go to Osh at this hour.
The safest option? Leave Dushanbe super early, and then get on a marshrutka to the border in Isfara. On the Kyrgyz side pay 50 Kyrgyz Som (they'll also take Tajik money) to get to the Batken bus station and hope that it's early enough to find a driver (but it will be too late for a marshrutka).
The trip in reverse (Osh to Dushanbe) is much easier. There are regularly scheduled morning departures from Osh to Batken by marshrutka. And on the Isfara side it will be much easier to find a driver to Dushanbe at late hours. If something goes wrong, you can just make the short trip to Khujand and spend the night there and go to Dushanbe the next morning. Check my instructions for how to do that trip from Osh to Khujand: viewtopic.php?t=10437
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I forgot to stress one thing: the time zone difference. Every time listed above is Tajikistan time. So if you are trying to make the 2pm Batken to Osh marshrutka when coming from the Tajik side, consider that that 2pm in Batken means 1pm on the Tajik side.
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