Red Dead Redemption 2 Urban Pleasures Walkthrough

Urban Pleasures is the 53rd main story mission in Red Dead Redemption 2 (RDR2). This walkthrough will guide you through all objectives of Urban Pleasures Main Quest including all Gold Medals for 100% completion.

Urban Pleasures is unlocked after completing Horsemen, Apocalypse.

Quest Giver: Dutch
Chapter: 4
Region: Lemoyne

Gold Medal Requirements:

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

Starting Location: Saint Denis, Lemoyne

Talk to Dutch

Dutch is ready to put part one of his plan to leave America into motion. Time to hit the Victory Street Trolley Station that Dutch has been talking about for ages, and its happening right now.

Seconds later you’re in the thick of it. Start robbing folk, and don’t leave anyone out. Easy to do since there’s only three of them.

GOLD MEDAL: Rob all the customers in the trolley station

Once you’ve robbed everyone, Dutch tells you to check the safe. Go behind the counter and threaten the cashier until he opens it.

Well that’s disappointing.

It gets worse. Bronte has set you up, and now you’re surrounded by police.

Running out the back door, the three of you get on the trolley and make your extremely linear getaway.

GOLD MEDAL: Kill 10 lawmen while on the trolley
GOLD MEDAL: Prevent any lawmen jumping on the back of the wagon
GOLD MEDAL: Complete the mission without taking any health items

You will be on the trolley for less than a minute, so its imperative that you don’t waste any time while getting kills. When you start there will be a cop straight ahead of you, but also three more along the sidewalk to the right. Don’t miss the opportunity for a Dead Eye spree.

When you go around the corner, there will be three more to the right, one right on the street, one on the balcony above, and one running out of the building with the balcony at ground level. Another round of Dead Eye will do the trick.

Shortly thereafter two riders will come up on your left side, and a third cop will be on the street nearby. Dead Eye again.

Immediately afterwards there will be two cops on the right, one on the ground, and one above on the balcony. This will be followed by a third further ahead at ground level. Last chance for Dead Eye.

After this, you’ll start moving so fast it triggers a cinematic. You have no brakes and no control. The trolley derails, smashing through anything in its way.

When you have control again, its just in time to take cover in another gunfight with the law. This plan is going so smooth.

Remember there are no accuracy requirements, just have to keep yourself alive. So feel free to spray and pray.

There will be a lot of police. Do your best to keep your head down. When there’s a break in the assault, Dutch will call for you to run. Follow Lenny to ‘safety’. Run into the back alley, taking out police on the balconies and stairs as you go.

Follow Lenny as he opens a gate to the next street. Police will seal off the north end of the street, forcing you south. Watch out for police on the balcony ahead, as well as mounted on the street.

Turn left at the corner and go down the street to the east, following Dutch and Lenny.

At the end of the block, take cover behind the wagon and shoot at the numerous police to the south, keeping an eye on one that pops up on the balcony above you.

South one block, you’ll juke west, making for a police wagon you can use for your escape.

Lenny will drive while you provide cover. There will be several riders that give chase immediately, in addition to whatever police on the ground you hadn’t cleared out.

Some will even try to jump on the wagon if you don’t kill them fast enough.

There will be several solid waves of police shooting at you. Return fire as best as you can, prioritizing riders.

Nearing the edge of the city, you’ll be within striking distance of escape when Lenny will notice that the road has been blocked. Ever helpful guy that he is, Dutch will offer him a stick of dynamite to use to clear them out.

GOLD MEDAL: Shoot the dynamite Lenny throws

You will automatically snap into Dead Eye as soon as Lenny throws the stick of dynamite. Shoot it as it flies through the air towards the blockade to complete the last gold medal requirement.