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Side stories inOctopath Traveler 2are a fantastic way to get lots of leaves (read: money), explore the world in new ways, and find great weapons and accessories. There are tons of these to find throughout the game, in most settlements.
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The Winterlands are home to a few settlements - Cape Cold, Winterbloom, and the late-game Stormhail. This snowy region doesn’t have all that many side quests when compared to the other regions of the game, but the few it does have can be a bit tricky to solve, as they require some headwork.
Reward
12,000 leaves, Sharp Nut (L) x1, Slippery Nut (L) x1
To begin this quest, head into theItem Shop in Stormhailand talk to the little girl here. It’s clear that something is up.

Getting information from theClingy Womanbehind the counter won’t reveal anything, butknocking her outwill. Use any one of your party members with that ability to knock her out, and a cutscene will reveal everything. You’ll get your reward straight after.
300 leaves, Magic Nut (M) x1, Refreshing Jam x1

You’ll find this father standing outside his house in Winterbloom. He needs a gift for his son, who is going to go traveling to become a scholar.
The item you need for this quest is theSilver Quill- you’ll find this item inCape Cold. Enter the house to the left of the area and use an item-taking Path Action totake it from the Retired Scholarwithin. Return to Winterbloom and give the item to the Thoughtful Father to complete the quest.

14,000 leaves, Alluring Ribbon x1
Talking to this woman, who is found to the east of Stormhail, will reveal that she’sholding onto a necklaceand with it, she can’t seem to let go of a past love. To solve this,use a Path Action to take the Treasured Necklace from her. This can be accomplished with Agnea, Throné, Osvald, or Partitio.

Once you’ve taken the necklace, a cutscene will begin with the Dismal Woman thanking you.
9,000 leaves, Melia’s Amulet

To begin this quest, you’ll need to havecompleted Castti’s story. Talk to Melia in Winterbloom to begin this quest.
Your first task in this quest is toinvestigate the Snowhares, who are located in theThieves' Quarterof Winterbloom, to the north.Enter the tavernthere to witness a cutscene. After the scene, use an item-obtaining Path Action to get theLetter from the Snowharesfrom Plukk.

You can take this opportunity tofight the trio of Snowharesat the same time using a Path Action, such as Ochette’s Provoke, but you won’t get much of a prize for beating them, and it won’t progress the quest.
Return to Melia with the Letterand hand it to her. After the following cutscene, you’ll get your reward.

6,000 leaves, Peddler’s Feathered Cap x1
The questgiver for this quest is one of the rare individuals who hang out outside a settlement - you’ll find him byheading east from Cape Cold. His issue is that there is a Ruffian preventing him from obtaining his wares from the Ruffians' Hideout, which is to the east.

There are two ways to deal with this quest:
Inside the Ruffians' Hideout, explore the area to get a few decent items. There’s aBottle of Blinding Dustin a chest near the entrance by land,1,000 leavesfurther to the right from there, and theHeretic’s Greatswordon the far right side of the area.
On the northern bank of the river, which you’re able to access via a small dock, you’ll find a chest containing anOlive of Life (M)and the Ruffians themselves.

Walk up to the Ruffians,‘and a cutscene will start. The fight is very easy - none of the Ruffians have more than 2,000 HP. Attacks that hit the entire enemy party will finish the fight quickly.
After the battle, the Ruffians will leave and you can open the chest left behind to get aWind Robe. Return to thePeddlerin the previous area to finish the quest and get your reward.

3,000 leaves, Nourishing Nut x1
This man is found right at the entrance to Cape Cold and requires the help of amidwife. Unfortunately, the midwife is currently inFlamechurch.
As hinted at, you’ll find the Midwife in Flamechurch.She’s located in the Innand can be found regardless of the time. You’ll need toadd her to your party using one of the four Guide Path Actions. Return to Cape Cold with the Midwife in tow andtalk to the Flustered Villager againto complete the quest.
7,000 leaves, Rusty Sword x1, Revitalizing Jam x1
This woman, found to the east of Winterbloom, needs helpremoving a sword from a stone. There are two ways to help her do this.
The first is tohead to Oresrush and enter the Weapon Shopin the northeast part of town. Inside is aRetired Miner who has a Sturdy Pickaxe. Obtain this item with an item-obtaining Path Action and use this to retrieve the sword from the stone back in Winterbloom.
The second is to use a party ofPartitio, Temenos, Agnea, and Ochetteand have all four party members recruit an NPC. That way, you’ll haveeight peoplewith which to pull the sword from the stone.
TheRusty Swordyou obtain from this quest is one of the six weapons that unlockskills for the secret Armsmaster class. It is actually theConqueror’s Sword, and taking it to the Armsmaster in Gravell will let you use it as it’s meant to be used.
6,600 leaves, Jade Dagger x1
To start this quest, you’ll first need to acquirePartitio’s boat. If you haven’t acquired it yet,check out this guide.
Enter thesea mapand dock your ship onLighthouse Island, which you’ll find just to the west of Cape Cold. Once you’re here, talk to theLighthouse Keeper’s Wifeoutside and accept thebottled message.
While you’re here, make sure you grab theAelmorite Reflector from the Lighthouse Keeperwho should be inside the lighthouse. This is used in another quest. There’s also a red chest on the cliff to the west that contains12,000 leaves, and another on the east side that contains anOctopuff Pot.
You’re looking for a women namedRuby in Timberain. She’s located on the upper level of the town,just to the left of the courthouse. Deliver her the letter and hear her story. You’ll get the quest reward here, you don’t have to return to Lighthouse Island.