Not every encountered should mean trouble or harm to the PC, otherwise the players will start to shun every event to the best of their abilities (and rightly so!). Thereby, I offer you six beneficial events for “vanilla” fantasy OSR games.
01# The characters have a chance encounter with a traveling level 1 cleric of a benevolent deity. If they share their story with him or her and they seem in need of help, the cleric will either cast a Cure Minor Wounds or a Bless spell for them.
02# In a village inn or a guest house along the road the characters meet 1d3 merchants that travel together and just happen to head into the same direction as the characters do. While they already have hired guards to protect their wagons (one wagon per merchant, and three more guards than there are wagons) they are not averse to having a few more “honorable, capable folk” along and offer to supply the adventurers with provisions for each day they travel with them down the road.
03# After a junction or crossroad the characters meet a dwarf who drags two heavy sacks behind him, each about as large as he is himself. He sweats and curses while he pulls them along, inch by inch, and his face is already deep red from exertion. When the characters approach he will stop and raise a hand for a greeting (while he puts the other to the small hatchet on his belt), but will need a moment to catch his breath enough to introduce himself.
Larwin, a young smith (for a dwarf) wanted to offer a load of his tools and weapons for sale in the next human settlement, but his mule broke itself a leg “in one of these bedamnable potholes on this shoddy, useless things YOU call a road!”. He will be very reluctant to accept help to carry his wares (as he is afraid that “ye long-legs just run away with it!”) but he will gladly sell some of it to the characters “for a special price”. The bags (which are stuffed with hay for padding) contain an assortment of tools as well as a helmet, an ax, a mace, a warhammer, a short sword and a small shield, all of good quality. If the characters can somehow gain Larwin´s trust so that he accepts their help he will offer them “one of my wares of your choice for hauling them with me to the settlement”.
04# A hamlet the characters pass through celebrates the marriage of their liege, who has sponsored a few barrels of beer for this occasion. The people are joyful and welcome the characters as guests at the celebration . Food, drink and lodging (in the hay of one of the barns) are free this night.
05# In a tavern the characters meet a traveling bard who approaches them politely. “You seem to be an adventurous lot, from the look of you all. Do you have good stories to share? I am always interested in hearing interesting tales and your throats shall not dry why you tell them”. While he will only order the cheapest beer the house has to offer, those drinks will be on him if the characters have some good stories to share. If they have performed something exceptional, they might even be mentioned in one of his songs in the future.
06# In a guest house that is about a days march away from the next city or settlement, the characters are approached by the owner after they have been served their drinks: “Excuse me, good sirs… you look like fine fighting men. May I ask if you would be interested in a fine weapon?” A luckless adventurer entered the guest house a week before, a heavily armored man who looked liked a veteran mercenary. He downed the first tankard of double beer before the bar wench was even able to ask for the payment, and as she did he gave a sinister laugh, stood up and drew one of the weapons he wore (an ornamented short sword). “HERE!” he shouted and slammed it onto the table “that is enough to quench my thirst AND to pay for lodging, OR ISN´IT?!” The way he looked at the owner as he bellowed this made it clear that this wasn´t a question, especially as his hand had moved to the ax he still carried on person. Now, the owner tries to cut his losses on that “customer” and is eager to sell the short sword for 60% of the list price. The weapon has no special qualities, but my be sold for up to 120% of the list price if the characters find somebody that is interested in a fancy short sword.