Making Town Visits Engaging

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In D&D, we have multiple sets, each with a gameplay pattern to it.
Dungeon: wherein parties wind around in hollow spaces, retrieve treasure, and survive the trip back.
Wilderness: wherein parties map the area, finding fun places, even dungeons.
Settlements: ???

1. Adventurers enter settlements to:
    Sell/buy supplies
    Improve/repair equipment
    Heal (rest)
    Cure ailments
    Replenish magic
    Identify magic items & scrolls
    Recruit NPCs
    Hear rumors and news of the outside

2. How can I make these processes more fun? Some ideas:
    For inn rest: room quality (by price) determines % of max hp healed, and I describe lodging condition fluff (or player does).
    Rumors are a motley of true and false information.
    Hirelings and Henchmen are rolled up by the PC's player, but the DM gives each of them secrets and back story that become apparent over time. Role-playing these characters is shared between PC and DM (I haven't had problems doing this yet).
    Making an offering at a shrine allows a cleric to pick one of her prayers instead of randomly receiving it (within the theme of the shrine). The level picked determines the required offering. This is detailed more in my homebrew edition.
    A Random Town Events Table, which could offer hooks and changes from the usual services and role-play opportunities.

What are your ideas? Perhaps they were even accidents during play, but what made a city or village fun for your group?

I think that what makes a town scenario fun is letting the players do what THEY think is fun.  This requires that you have a general idea of the nature of the town and are able to wing it beyond that, but you need to limit this if not every player wants this type of "down" time.  I've had players decide to do things like try and buy out the local blacksmith or other shops to become a business person.  Players who randomly knocked on doors, saying very bizarre things to the occupants just to see what would happen (I had fun with this), and players who always try to start "trouble" in general in various ways.   If you can run with the scenarios the players create (as a break for them from the set-piece adventures they normally see) this can be great fun for everyone.

You can, of course, also run some surprise planned encounters in town.  I'm not a fan of random tables anymore unless they are used simply to help give you additional ideas - some suggestions:
1) The classic - PC is pick-pocketed and catches a glimpse of the thief melting away in the crowd (chase ensues which could lead to anything)
2) PC is identified as the lost lover of a townsperson - who is quite insistent that the PC is the person they claim (again this can develop in many ways or just be a throw away event)
3) A chance encounter with an important person in town makes an enemy - noble bumps into PC etc. - person now really has it in for the PCs and uses influence to impact them - shop prices go way up for them suddenly for instance (this can lead to many interesting developments too)

So the theme is stuff that can develop into more or not, and the beauty is you can use your player's initial reaction to actually decide whether to develop something or let it be a throw away encounter.

Definitely need some basic resources like a list of names to use on the fly, a general idea of how the economy of the settlement works, who is in charge, and how peace is kept (or not).  With these basics it can be fun to improvise.
The town itself can be treated as a dungeon, with the complication that most NPCs are not something to kill.

The party can be approached by A to do something, attack something, retrieve something, acquire some information...

... and then be approached by B which might alter or even completely reverse the party's plans...

... the task can be political, detective-work, police, or ???? without even leaving town. Or it might involve going to another town. Or....
"The world does not work the way you have been taught it does. We are not real as such; we exist within The Story. Unfortunately for you, you have inherited a condition from your mother known as Primary Protagonist Syndrome, which means The Story is interested in you. It will find you, and if you are not ready for the narrative strands it will throw at you..." - from Footloose
Several of the things you listed (identifying items, leveling up, healing, inn prices) are essentially book-keeping issues, which are never going to be "fun" or even particularly engaging. Look for story elements (as the other posters have suggested), not mechanics-related ones.
Several of the things you listed (identifying items, leveling up, healing, inn prices) are essentially book-keeping issues, which are never going to be "fun" or even particularly engaging. Look for story elements (as the other posters have suggested), not mechanics-related ones.

That's a good point.  No one wants to watch a scene in an action movie where Arnold Schwarzenegger has to go to the gun store to buy bullets.
DM advice: 1. Do a Session Zero. 2. Start With Action. 3. Always say "Yes" to player ideas. 4. Don't build railroads. 5. Make success, failure, and middling rolls interesting. Player advice: 1. Don't be a dick. 2. Build off each other, don't block each other. 3. You're supposed to be a badass. Act like it. Take risks. My poorly updated blog:
That's a good point.  No one wants to watch a scene in an action movie where Arnold Schwarzenegger has to go to the gun store to buy bullets.

Exactly. The issue is really in how a group approaches the game. If you frame your game in terms of a particular genre or design it like a TV show or movie, then stuff like this will be glaringly boring and you'll know to handwave it in favor of more action (or at least more plot relevant interaction). But a lot of groups still approach D&D the way they learned it "way back when," everything is "on-camera" and most PC actions aren't just assumed to have happened. While that's fine if you're having fun with it, it wouldn't be my preference. If I'm going to send 10-15 minutes on a scene, it better have some relevance because I only get X number of hours to game per week. I don't want to be spending it at the grocery store.

However, if my players have things to do that are plot relevant and are interested in having a session spent in town, I will do my best to both get their "errands" done AND make it exciting and fun. How you do that will depend specifically on your campaign and group.

For any decision or adjudication, ask yourself, "Is this going to be fun for everyone?" and "Is this going to lead to the creation of an exciting, memorable story?"

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Every time the party I'm a player in reaches the town, we're exstatic. We -love- our gold! We had some problems with party members stealing/hiding stuff from party members before, so we have an adventuring "contract" that my character made so we'd stop backstabbing each other. It has rules on how stuff gets split, who pays for what identifying costs, etc... It works great for us, we don't experience it as "bookkeeping" at all.

The identifying/appraisal itself is pretty satisfying. We get to find out what this stuff we were dragging along is worth, what it does, who wants to use it, etc... The rest gets sold off, and then we get to take a look at the merchant's inventory to see if there's any goodies we want there. So it's like opening a double treasure box, once for the identifying, once for the merchant's stock(which was limited at that time due to us being isolated on an island).

So yeah, the point of this is to illustrate that, even though others in this thread seem to think of it as not-fun, my party has an incredible amount of fun with all the "mundane" identifying and shopping. Talk to your party, see what they like.

When it's not buy-buy, sell-sell time though, our DM's town usually have a plethora of random plots going on we could stumble upon. Not all of those have to be resolved(or even discovered) but cool stuff generally happens if we do. Except if we do something stupid, then less cool stuff happens. Which is also cool, because it makes the world sufficiently dangerous and exciting. It's good to know our actions have consequences, good and bad, even in town ^^
..look around our world for other countries' holidays nobody knows about and then add them or part of them into your cities - I think breaking the monotony of the city trek could make it interesting.. (perhaps the Ritual of Steel festival has all the blacksmiths forging in a competition in the town square, and as such the party can not get the needed repairs) ..I got the idea from another DM at a local gaming store and he would bring snacks native to the country..

..good luck to you and all that jazz..
A little nonsense now and then is relished by the wisest men. - Willy Wonka
Every NPC I create I try to make a 3 to 5 bullet history or story. If I am careful enough I can create a social network of connection relationships. I've had players get mixed up in the politics of competing merchants, get into bidding wars, become a part of underground networks, become links in chains of command, etc etc.

It takes an amount of creativity, and an understanding that you're playing a roleplaying game. If your players get antsy when they're not killing something, then you may wanna just pick your battles here (pun somewhat intended). Frankly, I don't think I could stand having players who find NPC interactions boring, and I'd do my best to be as yielding to plot and story to lead them through sudden changes of pace. But if they just wanna kill.. well.. you may have a lot of people around your towns looking for sell-swords I guess.

If you need help with filling in NPC's, I found this awesome tool online.

Decide the size of the settlement, distribute the population, and this will give you everything. Names, occupations, dispositions, motivations, and all sorts of little cues for DM's to spin away and make all kinds of connections and leads for players to get involved in.

When I have a player finda  magic dagger, it isn't just a +1 dagger. It's the fabled Silver Key, a dagger knicked from the King's royal wizard who specialized in transmutation, passed hand by bloody fist from brigand to highwayman, all claiming to be the next big thief in the area. Players learn this from enthusiastic bards at street corners, eager to get a new story from the adventurers on how they found such an item. Or maybe a greedy merchant who lies about the dagger's true worth and ability, trying everything he can to get the dagger into his own hands so he can finally one up his rival who stole the best shop front in unfair politics.

For me, going into town should be the time to shine. This is where story is interwoven with quite a chaotic series of chance.
Create an encounter table. Roll % die to see what players stumble into, what they hear, who they may befriend.
This should be no different than a dungeon; the twists and turns are all there, and there are plenty of traps and puzzels to throw at your players. 
..oh snaps, do you know what I forgot - NPC mannerisms.. ..I has an NPC "planar guide" to the PC's and he was always late getting to the door, and would nod his head and always say.. .."hrmm hrmm" even if they PC's were saying the most mundane of details..

..and UGH!  ..I play alot of my cities with 2 npc gnome buiseness men, named Jinx and Winx, their background is clouded, they always seem to be at the right place at the right time.. IS a joke, but.. ..but it breaks the monotony.. gives you (the DM) .. ..well it gives me at any rate.. ..a reason to RP repairing gear and selling items and staying at the INN.. ..the Inns, that is what they are really known for.. .. has almost gotten to the point where my PC's seek them out when they get to a new city..'s um..'s fun..
A little nonsense now and then is relished by the wisest men. - Willy Wonka
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