There is a common truism thrown around that the average medieval person never travelled more than 20 miles from their place of birth. If anyone else knows where this figure is drawn from I'd love to know...

That being said, for all the peasants who never travelled beyond their local area there were quite a few folks traveling in the medieval world, especially as you get later and later.

Merchants, pilgrims, soldiers, kings, diplomats/envoys, mendicants and more all traveled, using a variety of methods.

I'll give you a few examples and potential time frames from the Early Middle Ages and maybe some other folks can pitch in as well.

• Merchants: We know that there was active trading going on both in the North Sea and the Mediterranean. Merchants would have largely traveled by water (river and sea) as this was both the fastest and cheapest way to move goods. The amount of time it took would depend on the destination of course (it would take longer to go up the Rhine than down it, for instance) but we can calculate some average time/distance calculations for North Sea trade.

Stéphane Lebecq estimates that a northern ship could sail roughly 30 miles a day (50-60 km) if stops were made at night and for trade, and perhaps twice that if no stops were made. So a trip from Dorestad (near Utrecht) to London would take roughly four days, or from Dorestad to Hedeby (also known as Haithabu or Schleswig and located on the Eastern side of the Jutland peninsula) about 5-10 days depending on stops. As he points out

these numbers are very theoretical. As a matter of fact, we know that Early Medieval seamen hugged the coast-line as far as possible, until the Vikings began to venture into the open sea. They could stay a long time in a port of call, waiting for messages, connections or consignments of goods. They could be stopped or slowed down in the wind turned or fell, though we know thanks to recent experiments achieved by the Roskilde Viking Ships Museum that, with a single square sail, Early Medieval ships could tack into the wind. Last but not least, they were threatened by the risks of storm, and, more and more important from the end of the 8th century, by the risks of piracy. Lebecq, Long Distance Merchants and the Forms of their Ventures at the Time of the Dorestad Heyday in In Discussions with the Past

So that is an example of how long it might take for a trade ship to move around the North Sea. Lets look at another case of travel.

• Kings: Kings and emperors like Charlemagne and Louis the Pious traveled regularly, on fairly standard paths, confined largely to the heartland of the Frankish Empire with the occasional trip outward to Saxony or Rome depending on circumstances. As they traveled with their court (including clerics, guards, servants, family, court officials, hangers on etc.) they would make stops at various royal estates for food/shelter and also handle business in different locations. These trips would be slow and rambling, the main goal, however, was to end up at specific royal sites or assembly locations. We can use Annals, which give a pretty constant update about where the King and his court spent their time to get some idea of how long a trip might take. So for instance, in 800 Charlemagne left Aachen in March and traveled around the Gallic Coast, and then celebrated Easter at St-Riquier, so a roughly 240 mile trip took at least a few weeks to make. From there he traveled south to Tours and was there by the beginning of June, so again thats a trip of a little less than 300 miles that took at least 4-6 weeks. After this he went from Tours to Paris, then Orléans and then back to Aachen and then by August he had made his way to Mainz. Now things take a quick turn as Charlemagne decided to go to Italy. So sometime from late August to September the Emperor, alongside an Army, make their way to Ravenna and then down to Rome by the end of November. So a trip from Germany to Italy (roughly 800 miles), with an army, takes anywhere from 2-3 months all told.

These trips could clearly have gone faster if Charlemagne wasn't stopping to oversee various governmental things, deal with person matters or religious ceremonies or gather armies, but perhaps you get a sense of the speed of things from this account.

I'm going to let someone else take a crack at Pilgrims, Crusaders etc. We have a pretty decent idea of time frames, but it is hard to determine an "average" from the specific accounts we have.

A few places to go for more info.

Michael McCormick's tome Origins of the European Economy has great stuff on travel, trade and time in it. It is huge, but you can sift through it.

Also check out this awesome digital-humanities project from Stanford, called ORBIS, it allows you to calculate time and distance traveled in the Roman World. Obviously it is not possible to apply everything here to the medieval world (important places changed, roads deteriorated, different technologies and practices etc.) but it can give you some ideas about travel in the pre-modern world.

Because I am not a medieval historian, I cannot answer all your questions, but, I still have a book from my "History of Medieval Cities" class in college, and I pulled it out because I think it will answer some of your questions.

Life in A Medieval City By Joseph and Frances Gies (published by Harper Perennial) goes into this specifically. The book is an in-depth study of the city of Troyes, France, during the High Middle Ages, but focusing around the middle of the 13th century.

When talking about merchants who are transporting pack animals: "In level country pack animals can make fifteen to twenty miles a day, carrying three to four hundred pounds [each.]" It goes on to explain that couriers who operated between Champagne Fairs and Ghent which covered two hundred miles could make the trip in four days if weather permitted. Page 25.

They also discussed nuisances to merchants, the worst of which were tolls. This made traveling across rivers and vast stretches of land very costly for the average person: Page 25-28

On who could afford horses or other options besides walking: "Only novels and rich burghers ride horses; everyone else rides donkeys or walks. A pregnant lady or wounded knight may be carried in a litter (carriages are far in the future)." Page 88.

When you were asking about various towns having their own Robin Hood, the answer is a resounding no. Most leaders, whether Kings, Dukes, Counts, etc. honored treaties with one another to protect their roads. Although some areas were very dangerous, thieves stayed away from merchants who were crossing on their land because of retribution by the local lord. This was especially true in the Spring time when the winter snows melted and merchants were moving back in for the fairs that each city/region had. Pages 30-32

I hoped I helped shed a little light on this topic. I highly recommend that book because it's rather engaging and very extensively researched.