diff --git a/arcade/__init__.py b/arcade/__init__.py
index 3fd5a932d7..006f858746 100644
--- a/arcade/__init__.py
+++ b/arcade/__init__.py
@@ -58,29 +58,18 @@ def configure_logging(level: Optional[int] = None):
 # noinspection PyPep8
 import pyglet
 
-# TODO: Remove ASAP after pyglet >= 2.1dev2 is out
-if pyglet.version == "2.1.dev2":
-    # Temporary monkeypatch via deletion since dev2 still includes
-    # overly-specific __eq__ behavior. Later pyglet commits restore
-    # equality with same-valued tuples by deleting the __eq__ methods.
-    from pyglet import math as _pyglet_math
-
-    del _pyglet_math.Vec2.__eq__
-    del _pyglet_math.Vec3.__eq__
-    del _pyglet_math.Vec4.__eq__
-
 # Env variable shortcut for headless mode
 if os.environ.get("ARCADE_HEADLESS"):
-    pyglet.options["headless"] = True
+    pyglet.options.headless = True
 
 from arcade import utils
 
 # Disable shadow window on macs and in headless mode.
 if sys.platform == "darwin" or os.environ.get("ARCADE_HEADLESS") or utils.is_raspberry_pi():
-    pyglet.options["shadow_window"] = False
+    pyglet.options.shadow_window = False
 
 # Use the old gdi fonts on windows until directwrite is fast/stable
-# pyglet.options['win32_gdi_font'] = True
+# pyglet.options.win32_gdi_font = True
 
 # Imports from modules that don't do anything circular
 
@@ -152,7 +141,7 @@ def configure_logging(level: Optional[int] = None):
 from .screenshot import get_pixel
 
 # We don't have joysticks game controllers in headless mode
-if not pyglet.options["headless"]:
+if not pyglet.options.headless:
     from .joysticks import get_game_controllers
     from .joysticks import get_joysticks
     from .controller import ControllerManager
@@ -420,11 +409,12 @@ def configure_logging(level: Optional[int] = None):
     load_font(":system:fonts/ttf/Kenney_Rocket_Square.ttf")
 
     # Load additional game controller mappings to Pyglet
-    if not pyglet.options["headless"]:
+    if not pyglet.options.headless:
         try:
             import pyglet.input.controller
 
             mappings_file = resources.resolve(":system:gamecontrollerdb.txt")
-            pyglet.input.controller.add_mappings_from_file(mappings_file)
+            # TODO: remove string conversion once fixed upstream
+            pyglet.input.controller.add_mappings_from_file(str(mappings_file))
         except AssertionError:
             pass
diff --git a/arcade/application.py b/arcade/application.py
index 065c730494..eeba095c05 100644
--- a/arcade/application.py
+++ b/arcade/application.py
@@ -112,14 +112,14 @@ def __init__(
         self,
         width: int = 1280,
         height: int = 720,
-        title: Optional[str] = "Arcade Window",
+        title: str | None = "Arcade Window",
         fullscreen: bool = False,
         resizable: bool = False,
         update_rate: float = 1 / 60,
         antialiasing: bool = True,
         gl_version: tuple[int, int] = (3, 3),
-        screen: Optional[pyglet.display.Screen] = None,
-        style: Optional[str] = pyglet.window.Window.WINDOW_STYLE_DEFAULT,
+        screen: pyglet.display.Screen | None = None,
+        style: str | None = pyglet.window.Window.WINDOW_STYLE_DEFAULT,
         visible: bool = True,
         vsync: bool = False,
         gc_mode: str = "context_gc",
@@ -129,7 +129,7 @@ def __init__(
         gl_api: str = "gl",
         draw_rate: float = 1 / 60,
         fixed_rate: float = 1.0 / 60.0,
-        fixed_frame_cap: Optional[int] = None,
+        fixed_frame_cap: int | None = None,
     ) -> None:
         # In certain environments we can't have antialiasing/MSAA enabled.
         # Detect replit environment
@@ -142,7 +142,7 @@ def __init__(
             gl_api = "gles"
 
         #: Whether this is a headless window
-        self.headless: bool = pyglet.options.get("headless") is True
+        self.headless: bool = pyglet.options.headless is True
 
         config = None
         # Attempt to make window with antialiasing
@@ -248,7 +248,7 @@ def __init__(
         if enable_polling:
             self.keyboard = pyglet.window.key.KeyStateHandler()
 
-            if pyglet.options["headless"]:
+            if pyglet.options.headless:
                 self.push_handlers(self.keyboard)
 
             else:
@@ -365,10 +365,10 @@ def close(self) -> None:
     def set_fullscreen(
         self,
         fullscreen: bool = True,
-        screen: Optional["Window"] = None,
-        mode: Optional[ScreenMode] = None,
-        width: Optional[float] = None,
-        height: Optional[float] = None,
+        screen: pyglet.window.Window | None = None,
+        mode: ScreenMode | None = None,
+        width: float | None = None,
+        height: float | None = None,
     ) -> None:
         """
         Set if we are full screen or not.
@@ -380,10 +380,18 @@ def set_fullscreen(
                 have been obtained by enumerating `Screen.get_modes`.  If
                 None, an appropriate mode will be selected from the given
                 `width` and `height`.
-        :param width:
-        :param height:
-        """
-        super().set_fullscreen(fullscreen, screen, mode, width, height)
+        :param width: Although marked as py:class:`float`, will be
+            rounded via :py:class:`int` if not ``None``.
+        :param height: Although marked as py:class:`float`, will be
+            rounded via :py:class:`int` if not ``None``.
+        """
+        # fmt: off
+        super().set_fullscreen(
+            fullscreen, screen, mode,
+            # TODO: resolve the upstream int / float screen coord issue
+            None if width is None else int(width),
+            None if height is None else int(height))
+        # fmt: on
 
     def center_window(self) -> None:
         """
diff --git a/arcade/sound.py b/arcade/sound.py
index 977217bc26..554badf140 100644
--- a/arcade/sound.py
+++ b/arcade/sound.py
@@ -11,15 +11,14 @@
 from typing import Optional, Union
 
 import pyglet
+from pyglet.media import Source
 
 from arcade.resources import resolve
 
 if os.environ.get("ARCADE_SOUND_BACKENDS"):
-    pyglet.options["audio"] = tuple(
-        v.strip() for v in os.environ["ARCADE_SOUND_BACKENDS"].split(",")
-    )
+    pyglet.options.audio = tuple(v.strip() for v in os.environ["ARCADE_SOUND_BACKENDS"].split(","))
 else:
-    pyglet.options["audio"] = ("openal", "xaudio2", "directsound", "pulse", "silent")
+    pyglet.options.audio = ("openal", "xaudio2", "directsound", "pulse", "silent")
 
 import pyglet.media as media
 
@@ -39,7 +38,7 @@ def __init__(self, file_name: Union[str, Path], streaming: bool = False):
             raise FileNotFoundError(f"The sound file '{file_name}' is not a file or can't be read.")
         self.file_name = str(file_name)
 
-        self.source: Union[media.StaticSource, media.StreamingSource] = media.load(
+        self.source: Source = media.load(
             self.file_name, streaming=streaming
         )
 
diff --git a/arcade/text.py b/arcade/text.py
index a90fbbbe22..b9a436a2f1 100644
--- a/arcade/text.py
+++ b/arcade/text.py
@@ -45,9 +45,8 @@ def load_font(path: Union[str, Path]) -> None:
 FontNameOrNames = Union[str, tuple[str, ...]]
 
 
-def _attempt_font_name_resolution(font_name: FontNameOrNames) -> FontNameOrNames:
-    """
-    Attempt to resolve a tuple of font names.
+def _attempt_font_name_resolution(font_name: FontNameOrNames) -> str:
+    """Attempt to resolve a font name.
 
     Preserves the original logic of this section, even though it
     doesn't seem to make sense entirely. Comments are an attempt
@@ -82,8 +81,12 @@ def _attempt_font_name_resolution(font_name: FontNameOrNames) -> FontNameOrNames
             except FileNotFoundError:
                 pass
 
-    # failed to find it ourselves, hope pyglet can make sense of it
-    return font_name
+        # failed to find it ourselves, hope pyglet can make sense of it
+        # Note this is the best approximation of what I unerstand the old
+        # behavior to have been.
+        return pyglet.font.load(font_list).name
+
+    raise ValueError(f"Couldn't find a font for {font_name!r}")
 
 
 def _draw_pyglet_label(label: pyglet.text.Label) -> None:
@@ -131,7 +134,8 @@ class Text:
     :param width: A width limit in pixels
     :param align: Horizontal alignment; values other than "left" require width to be set
     :param Union[str, tuple[str, ...]] font_name: A font name, path to a font file, or list of names
-    :param bold: Whether to draw the text as bold
+    :param bold: Whether to draw the text as bold, and if a string,
+        how bold. See :py:attr:`.bold` to learn more.
     :param italic: Whether to draw the text as italic
     :param anchor_x: How to calculate the anchor point's x coordinate.
                          Options: "left", "center", or "right"
@@ -180,7 +184,7 @@ def __init__(
         width: int | None = None,
         align: str = "left",
         font_name: FontNameOrNames = ("calibri", "arial"),
-        bold: bool = False,
+        bold: bool | str = False,
         italic: bool = False,
         anchor_x: str = "left",
         anchor_y: str = "baseline",
@@ -203,6 +207,7 @@ def __init__(
             )
 
         adjusted_font = _attempt_font_name_resolution(font_name)
+
         self._label = pyglet.text.Label(
             text=text,
             # pyglet is lying about what it takes here and float is entirely valid
@@ -210,13 +215,14 @@ def __init__(
             y=y,  # type: ignore
             z=z,  # type: ignore
             font_name=adjusted_font,
-            font_size=font_size,
+            # TODO: Fix this upstream (Mac & Linux seem to allow float)
+            font_size=font_size,  # type: ignore
             # use type: ignore since cast is slow & pyglet used Literal
             anchor_x=anchor_x,  # type: ignore
             anchor_y=anchor_y,  # type: ignore
             color=Color.from_iterable(color),
             width=width,
-            align=align,
+            align=align,  # type: ignore
             bold=bold,
             italic=italic,
             multiline=multiline,
@@ -385,7 +391,7 @@ def color(self) -> Color:
         """
         Get or set the text color for the label
         """
-        return self._label.color
+        return Color.from_iterable(self._label.color)
 
     @color.setter
     def color(self, color: RGBOrA255):
@@ -484,14 +490,23 @@ def align(self, align: str):
         self._label.set_style("align", align)
 
     @property
-    def bold(self) -> bool:
+    def bold(self) -> bool | str:
         """
-        Get or set bold state of the label
+        Get or set bold state of the label.
+
+        The supported values include:
+
+        * ``"black"``
+        * ``"bold" (same as ``True``)
+        * ``"semibold"``
+        * ``"semilight"``
+        * ``"light"``
+
         """
         return self._label.bold
 
     @bold.setter
-    def bold(self, bold: bool):
+    def bold(self, bold: bool | str):
         self._label.bold = bold
 
     @property
@@ -587,7 +602,7 @@ def create_text_sprite(
     width: int | None = None,
     align: str = "left",
     font_name: FontNameOrNames = ("calibri", "arial"),
-    bold: bool = False,
+    bold: bool | str = False,
     italic: bool = False,
     anchor_x: str = "left",
     multiline: bool = False,
@@ -675,7 +690,7 @@ def draw_text(
     width: int | None = None,
     align: str = "left",
     font_name: FontNameOrNames = ("calibri", "arial"),
-    bold: bool = False,
+    bold: bool | str = False,
     italic: bool = False,
     anchor_x: str = "left",
     anchor_y: str = "baseline",
@@ -715,7 +730,8 @@ def draw_text(
     :param width: A width limit in pixels
     :param align: Horizontal alignment; values other than "left" require width to be set
     :param Union[str, tuple[str, ...]] font_name: A font name, path to a font file, or list of names
-    :param bold: Whether to draw the text as bold
+    :param bold: Whether to draw the text as bold, and if a :py:class:`str`,
+        how bold to draw it. See :py:attr:`.Text.bold` to learn more.
     :param italic: Whether to draw the text as italic
     :param anchor_x: How to calculate the anchor point's x coordinate
     :param anchor_y: How to calculate the anchor point's y coordinate
diff --git a/doc/programming_guide/headless.rst b/doc/programming_guide/headless.rst
index 485d9e6786..4824cb1768 100644
--- a/doc/programming_guide/headless.rst
+++ b/doc/programming_guide/headless.rst
@@ -34,7 +34,7 @@ This can be done in the following ways:
 
     # The above is a shortcut for
     import pyglet
-    pyglet.options["headless"] = True
+    pyglet.options.headless = True
 
 This of course also means you can configure headless externally.
 
@@ -182,10 +182,10 @@ to a physical device (graphics card) or a virtual card/device.
 .. code:: py
 
     # Default setting
-    pyglet.options['headless_device'] = 0
+    pyglet.options.headless_device = 0
 
     # Use the second gpu/device
-    pyglet.options['headless_device'] = 1
+    pyglet.options.headless_device = 1
 
 Issues?
 -------
diff --git a/pyproject.toml b/pyproject.toml
index 404087a7fa..7956e68381 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -19,7 +19,7 @@ classifiers = [
     "Topic :: Software Development :: Libraries :: Python Modules",
 ]
 dependencies = [
-    "pyglet == 2.1dev2",
+    "pyglet == 2.1dev3",
     "pillow~=10.2.0",
     "pymunk~=6.6.0",
     "pytiled-parser~=2.2.5",
diff --git a/tests/__init__.py b/tests/__init__.py
index ca0a59529b..40bd75a955 100644
--- a/tests/__init__.py
+++ b/tests/__init__.py
@@ -3,4 +3,4 @@
 # Headless mode
 if os.environ.get("ARCADE_HEADLESS_TEST"):
     import pyglet
-    pyglet.options["headless"] = True
+    pyglet.options.headless = True