diff --git a/BaseClasses.py b/BaseClasses.py
index 551720bb..167495f8 100644
--- a/BaseClasses.py
+++ b/BaseClasses.py
@@ -18,10 +18,11 @@ from RoomData import Room
 
 class World(object):
 
-    def __init__(self, players, shuffle, doorShuffle, logic, mode, swords, difficulty, difficulty_adjustments,
+    def __init__(self, players, owShuffle, shuffle, doorShuffle, logic, mode, swords, difficulty, difficulty_adjustments,
                  timer, progressive, goal, algorithm, accessibility, shuffle_ganon, retro, custom, customitemarray, hints):
         self.players = players
         self.teams = 1
+        self.owShuffle = owShuffle.copy()
         self.shuffle = shuffle.copy()
         self.doorShuffle = doorShuffle.copy()
         self.intensity = {}
@@ -1926,6 +1927,7 @@ class Spoiler(object):
                          'retro': self.world.retro,
                          'weapons': self.world.swords,
                          'goal': self.world.goal,
+                         'ow_shuffle': self.world.owShuffle,
                          'shuffle': self.world.shuffle,
                          'door_shuffle': self.world.doorShuffle,
                          'intensity': self.world.intensity,
@@ -1991,6 +1993,7 @@ class Spoiler(object):
                 outfile.write('Goal:                            %s\n' % self.metadata['goal'][player])
                 outfile.write('Difficulty:                      %s\n' % self.metadata['item_pool'][player])
                 outfile.write('Item Functionality:              %s\n' % self.metadata['item_functionality'][player])
+                outfile.write('Overworld Shuffle:               %s\n' % self.metadata['ow_shuffle'][player])
                 outfile.write('Entrance Shuffle:                %s\n' % self.metadata['shuffle'][player])
                 outfile.write('Door Shuffle:                    %s\n' % self.metadata['door_shuffle'][player])
                 outfile.write('Intensity:                       %s\n' % self.metadata['intensity'][player])
diff --git a/CLI.py b/CLI.py
index 35204b65..da4803df 100644
--- a/CLI.py
+++ b/CLI.py
@@ -87,7 +87,7 @@ def parse_cli(argv, no_defaults=False):
         for player in range(1, multiargs.multi + 1):
             playerargs = parse_cli(shlex.split(getattr(ret,f"p{player}")), True)
 
-            for name in ['logic', 'mode', 'swords', 'goal', 'difficulty', 'item_functionality',
+            for name in ['logic', 'mode', 'swords', 'goal', 'difficulty', 'item_functionality', 'ow_shuffle',
                          'shuffle', 'door_shuffle', 'intensity', 'crystals_ganon', 'crystals_gt', 'openpyramid',
                          'mapshuffle', 'compassshuffle', 'keyshuffle', 'bigkeyshuffle', 'startinventory',
                          'retro', 'accessibility', 'hints', 'beemizer', 'experimental', 'dungeon_counters',
@@ -124,6 +124,7 @@ def parse_settings():
         # Shuffle Ganon defaults to TRUE
         "openpyramid": False,
         "shuffleganon": True,
+        "ow_shuffle": "vanilla",
         "shuffle": "vanilla",
 
         "shufflepots": False,
diff --git a/Gui.py b/Gui.py
index 4cc5b106..ff9b09f8 100755
--- a/Gui.py
+++ b/Gui.py
@@ -10,6 +10,7 @@ from source.gui.startinventory.overview import startinventory_page
 from source.gui.custom.overview import custom_page
 from source.gui.loadcliargs import loadcliargs, loadadjustargs
 from source.gui.randomize.item import item_page
+from source.gui.randomize.overworld import overworld_page
 from source.gui.randomize.entrando import entrando_page
 from source.gui.randomize.enemizer import enemizer_page
 from source.gui.randomize.dungeon import dungeon_page
@@ -107,6 +108,7 @@ def guiMain(args=None):
     # Randomize notebook page:
     #  make notebook pages: Item, Entrances, Enemizer, Dungeon Shuffle, Multiworld, Game Options, Generation Setup
     #   Item:             Item Randomizer settings
+    #   Overworld:        Overworld Randomizer settings
     #   Entrances:        Entrance Randomizer settings
     #   Enemizer:         Enemy Randomizer settings
     #   Dungeon Shuffle:  Dungeon Door Randomizer settings
@@ -122,6 +124,10 @@ def guiMain(args=None):
     self.pages["randomizer"].pages["item"] = item_page(self.pages["randomizer"].notebook)
     self.pages["randomizer"].notebook.add(self.pages["randomizer"].pages["item"], text="Items")
 
+    # Overworld Randomizer
+    self.pages["randomizer"].pages["overworld"] = overworld_page(self.pages["randomizer"].notebook)
+    self.pages["randomizer"].notebook.add(self.pages["randomizer"].pages["overworld"], text="Overworld")
+
     # Entrance Randomizer
     self.pages["randomizer"].pages["entrance"] = entrando_page(self.pages["randomizer"].notebook)
     self.pages["randomizer"].notebook.add(self.pages["randomizer"].pages["entrance"], text="Entrances")
diff --git a/Main.py b/Main.py
index 42a45fdd..22d4f4f5 100644
--- a/Main.py
+++ b/Main.py
@@ -39,7 +39,7 @@ def main(args, seed=None, fish=None):
     start = time.perf_counter()
 
     # initialize the world
-    world = World(args.multi, args.shuffle, args.door_shuffle, args.logic, args.mode, args.swords,
+    world = World(args.multi, args.ow_shuffle, args.shuffle, args.door_shuffle, args.logic, args.mode, args.swords,
                   args.difficulty, args.item_functionality, args.timer, args.progressive, args.goal, args.algorithm,
                   args.accessibility, args.shuffleganon, args.retro, args.custom, args.customitemarray, args.hints)
     logger = logging.getLogger('')
diff --git a/Mystery.py b/Mystery.py
index e0a19467..f81d2fc6 100644
--- a/Mystery.py
+++ b/Mystery.py
@@ -145,6 +145,8 @@ def roll_settings(weights):
 
     ret.accessibility = get_choice('accessibility')
 
+    overworld_shuffle = get_choice('overworld_shuffle')
+    ret.ow_shuffle = overworld_shuffle if overworld_shuffle != 'none' else 'vanilla'
     entrance_shuffle = get_choice('entrance_shuffle')
     ret.shuffle = entrance_shuffle if entrance_shuffle != 'none' else 'vanilla'
     door_shuffle = get_choice('door_shuffle')
diff --git a/README.md b/README.md
index 46d692f5..7dd03b75 100644
--- a/README.md
+++ b/README.md
@@ -121,6 +121,12 @@ Use to batch generate multiple seeds with same settings. If a seed number is pro
 
 Show the help message and exit.
 
+```
+--ow_shuffle <mode>     
+```
+
+For specifying the overworld shuffle you want as above. (default: vanilla)
+
 ```
 --door_shuffle <mode>     
 ```
diff --git a/resources/app/cli/args.json b/resources/app/cli/args.json
index 70bc1148..f41edd79 100644
--- a/resources/app/cli/args.json
+++ b/resources/app/cli/args.json
@@ -104,6 +104,14 @@
       "vt26"
     ]
   },
+  "ow_shuffle": {
+    "choices": [
+      "vanilla",
+      "simple",
+      "full",
+      "crossed"
+    ]
+  },
   "shuffle": {
     "choices": [
       "vanilla",
diff --git a/resources/app/cli/lang/en.json b/resources/app/cli/lang/en.json
index 556a0d13..9c7d048e 100644
--- a/resources/app/cli/lang/en.json
+++ b/resources/app/cli/lang/en.json
@@ -6,6 +6,7 @@
     "version": "Version",
     "seed": "Seed",
     "player": "Player",
+    "shuffling.overworld": "Shuffling overworld",
     "shuffling.world": "Shuffling the World about",
     "shuffling.dungeons": "Shuffling dungeons",
     "shuffling.pots": "Shuffling pots",
@@ -192,6 +193,16 @@
       "The dungeon variants only mix up dungeons and keep the rest of",
       "the overworld vanilla."
     ],
+    "ow_shuffle": [
+      "Select Overworld Shuffling Algorithm. (default: %(default)s)",
+      "Vanilla:        All overworld transitions are connected the same",
+      "                way they were in the base game.",
+      "Simple:         Overworld retains the same vanilla shape, but some overworld",
+      "                screens will be swapped with their opposite world version.",
+      "Full:           Overworld screen transitions will lead to other",
+      "                overworld screens from the same world.",
+      "Crossed:        Overworld screen transitions can lead to any other overworld screen."
+    ],
     "door_shuffle": [
       "Select Door Shuffling Algorithm. (default: %(default)s)",
       "Basic:          Doors are mixed within a single dungeon.",
diff --git a/resources/app/gui/lang/en.json b/resources/app/gui/lang/en.json
index 5351cd42..ad9277f2 100644
--- a/resources/app/gui/lang/en.json
+++ b/resources/app/gui/lang/en.json
@@ -109,6 +109,12 @@
     "randomizer.enemizer.enemizercli.online": "(get online)",
 
 
+    "randomizer.overworld.overworldshuffle": "Overworld Shuffle",
+    "randomizer.overworld.overworldshuffle.vanilla": "Vanilla",
+    "randomizer.overworld.overworldshuffle.simple": "Simple",
+    "randomizer.overworld.overworldshuffle.full": "Full",
+    "randomizer.overworld.overworldshuffle.crossed": "Crossed",
+    
     "randomizer.entrance.openpyramid": "Pre-open Pyramid Hole",
     "randomizer.entrance.shuffleganon": "Include Ganon's Tower and Pyramid Hole in shuffle pool",
 
diff --git a/resources/app/gui/randomize/overworld/widgets.json b/resources/app/gui/randomize/overworld/widgets.json
new file mode 100644
index 00000000..d2c594d2
--- /dev/null
+++ b/resources/app/gui/randomize/overworld/widgets.json
@@ -0,0 +1,12 @@
+{
+  "widgets": {
+    "overworldshuffle": {
+      "type": "selectbox",
+      "default": "vanilla",
+      "options": [
+        "vanilla",
+        "full"
+      ]
+    }
+  }
+}
diff --git a/source/classes/constants.py b/source/classes/constants.py
index 18bca6ac..32922049 100644
--- a/source/classes/constants.py
+++ b/source/classes/constants.py
@@ -69,6 +69,9 @@ SETTINGSTOPROCESS = {
       "accessibility": "accessibility",
       "sortingalgo": "algorithm"
     },
+    "overworld": {
+      "overworldshuffle": "ow_shuffle"
+    },
     "entrance": {
       "openpyramid": "openpyramid",
       "shuffleganon": "shuffleganon",
diff --git a/source/gui/randomize/overworld.py b/source/gui/randomize/overworld.py
new file mode 100644
index 00000000..350d0e31
--- /dev/null
+++ b/source/gui/randomize/overworld.py
@@ -0,0 +1,29 @@
+from tkinter import ttk, Frame, Label, E, W, LEFT, RIGHT
+import source.gui.widgets as widgets
+import json
+import os
+
+def overworld_page(parent):
+    # Overworld Shuffle
+    self = ttk.Frame(parent)
+
+    # Overworld Shuffle options
+    self.widgets = {}
+
+    # Overworld Shuffle option sections
+    self.frames = {}
+
+    # Load Overworld Shuffle option widgets as defined by JSON file
+    # Defns include frame name, widget type, widget options, widget placement attributes
+    # These get split left & right
+    self.frames["widgets"] = Frame(self)
+    self.frames["widgets"].pack(anchor=W)
+    with open(os.path.join("resources","app","gui","randomize","overworld","widgets.json")) as overworldWidgets:
+        myDict = json.load(overworldWidgets)
+        myDict = myDict["widgets"]
+        dictWidgets = widgets.make_widgets_from_dict(self, myDict, self.frames["widgets"])
+        for key in dictWidgets:
+            self.widgets[key] = dictWidgets[key]
+            self.widgets[key].pack(anchor=W)
+
+    return self