>>1302932first of all, how medieval? Like, early medieval (ie the viking period), 11-13th century, or late medieval?
First thing you need to realise, is that in this age, your pants don't have pockets, so your ability to stuff different doodads about your person is somwhat limited.
You're likely to have a knife, or two (a belt knife, like a seax, and a small utility knife, likely in a neck sheath).
Flint, and steel, are next.
Weapons, cause the roads are dangerous, so sword (if you can afford it, because it's easy to carry), but more likely an axe, or spear. Fighting axes don't make the best tools, but something like a fokos/valaska will work just fine, and some one handed axes as well. Otherwise, a woodcutter's axe.
A bedroll, wool blanket, cloak. Waterskin with some low % alcohol (mead, or wine), some food (bread, cheese).
Money, or other currency, like hacksilver, and if the settlements are truly distant, constituting a journey of several weeks, then you'd travel along the road and stay in inns, whenever possible.
