How far could a man in the medieval period travel? If a man was delivering a message, for example, York to Leicester, how long would it take vs. if a man was traveling with a retinue of men (archers, foot soldiers, wagons of weaponry) in a day's time.
Good question. So many variables to take into account.
Re. messenger:- What were the roadways like upon the chosen route? Which time of year? Presumeably travelling by horse then 10 miles per hour should be realistic speed, but the length of the journey would determine if replacement mounts were needed, and if so were they available? 1676 saw John 'Swift Nick' Nevison ride over 190 miles in around 15 hours. Starting at Gads Hill in Kent he changed horses finally at Black Horse Farm to the north of Aberford (then an inn on the Great North Road) before his last stretch into York. The roads were likely to be slightly better by that year, but that is very arguable.
The distances involved and the routes are the most important to consider. Roads around York would offer a likely 40 mile fast-track situation, whilst crossing the Pennines or negotiating rural regions would be slow going any time of year and totally impossible during a bad winter.
Re. a force of men:- I would think that 20-30 miles in a day would be the upper limit. The road conditions would be far more influencial to a retinue with baggage carts than they would be to a lone rider.
You obviously have something in mind. What prompted this travel question? Who was riding with a message and who was leading his men from X to Y??
Nottingham to Southampton - according to mapquest of today - 166 miles. The constable of Pembroke traveled from there to Nottingham to give Richard word he arrived in Wales and traveled 50+ miles a day. I've no source to confirm that but know the writer and know his work is well researched.
Southampton to Leicester - 109 miles - scenario there - outfitting the fleet so don't know if he was on land or sea. time of year - summer so roads would be dry - maybe, well most likely from what I read.
He would have traveled with his immediate retinue. I have discounted wagons of militia. why, I don't know but traveling with men on horseback, don't know if any were on foot.
No scout system here, just a household or retinue of men traveling. Would there be places to stop for fresh horses? Not likely.
I would think that the 109 miles could be done in a day. Depends if they were in a rush. Not likely from the scenario, but I am sure a lord could facilitate fresh horses if he wished - tho the distance is not impossible on one mount. Wouldn't have thought baggage would have been with them if it was a rush trip but if papers of state were needed then a cart might well be required.
Tho that could have travelled behind under seperate escort.