Red Dead Redemption 2 – Urban Pleasures Walkthrough

Urban Pleasures is a Main Story Mission and part of Red Dead Redemption 2 part four.

This guide highlights mission strategies and Gold Medal requirements.

Table of Contents

Urban Pleasures Mission

Gold Medal Checklist

  • Rob all the customers in the trolley station
  • Kill 10 lawmen while on the trolley
  • Prevent any lawmen jumping on the back of the wagon
  • Shoot the dynamite Lenny throws

Complete the mission without taking any health items

Start this mission by approaching Dutch and Lenny across the trolley station. Make sure to approach from the south – coming around back from the alley will glitch the game.

Immediately, you will all equip your masks, and brashly enter the trolly station, declaring it to be a robbery.


[su_note]You must rob every person here to meet a Gold Medal requirement.[/su_note]

Relieve the few people their of their personals, though it’s not much.

The room Lenny searches doesn’t have much, either. When the teller finally opens the door for you, you’ll find out shortly he, too, doesn’t have much. With very little to show for it, dozens of police show up. Your saving grace passes by as a trolley cart. Jump onto it with your friends to make a getaway… sort of.


[su_note]Kill 10 lawmen from the trolly during this sequence.[/su_note]

After a while, the trolley will begin to kareen out of control. Arthur discovers it’s broken – and you all brace for impact as it crosses paths with a carriage.

You crash, but luckily you’re all mostly okay, but there are still lawmen on your tail. Take cover while shooting, then go across the street when prompted. Follow Lenny through an alleyway, fighting as you go.

Listen to their hints – shooting where Lenny and Dutch say, and moving when they say as well. Take cover when you can. There’re plenty of wagons and other objects around.

Speaking of wagons, you’ll eventually turn a corner with a wagon on the street. Make sure not to damage it. When you can, jump on the wagon with your friends.


[su_note]Prioritize lawmen who are closer to you to prevent them from jumping on your getaway wagon.[/su_note]

Keep shooting as you make your way out of town. Eventually, you’ll make it to a bridge, but it’s completely blocked. Keep your eyes forward.


[su_note]We say to keep your eyes forward, because Dutch will ready a stick of Dynamite that Lenny will throw at the blockade. You have to be ready, facing the right direction, to go into Dead Eye to land this shot.[/su_note]

Shoot the stick of dynamite Lenny throws if you can, but if not, it will clear the way for you regardless. Once you make it past this point, you’ll be in the clear… for now. Technically, you’ve still amassed quite a large bounty.

Sadly, the loot you’ve got wouldn’t even put a tent in the bounty you accrued – about $15. This marks the end of the mission.

Red Dead Redemption 2 – Urban Pleasures mission is done.

Next is up: Country Pursuits

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