How to add horizontal separator in a dynamically created ContextMenu?

I have modified the solution provided by Rachel above to correct the Separator style. I realize this post is old, but still one of the top results on Google. In my situation, I was using it for a Menu vs a ContextMenu, but the same should work.

XAML

<Menu ItemsSource="{Binding MenuItems}">
    <Menu.Resources>
        <ControlTemplate x:Key="MenuSeparatorTemplate">
            <Separator>
                <Separator.Style>
                    <Style TargetType="{x:Type Separator}" BasedOn="{StaticResource ResourceKey={x:Static MenuItem.SeparatorStyleKey}}"/>
                </Separator.Style>
            </Separator>
        </ControlTemplate>
        <Style TargetType="{x:Type MenuItem}">
            <Setter Property="Header" Value="{Binding MenuItemHeader}" />
            <Setter Property="Command" Value="{Binding MenuItemCommand}" />
            <Setter Property="CommandParameter" Value="{Binding MenuItemCommandParameter}" />
            <Setter Property="ItemsSource" Value="{Binding MenuItemCollection}" />
            <Style.Triggers>
                <DataTrigger Binding="{Binding }" Value="{x:Null}">
                    <Setter Property="Template" Value="{StaticResource MenuSeparatorTemplate}" />
                </DataTrigger>
            </Style.Triggers>
        </Style>
    </Menu.Resources>
</Menu>

Without Separator Style Change

With Separator Style Change

I did this once and used a null as my separator. From the XAML, I then styled the template to use a separator if the datacontext was null

Code behind:

this.Commands.Add(MainWindow.AddRole4);
this.Add(null); 
this.Commands.Add(MainWindow.AddRole5);

XAML was something like this:

<ContextMenu.ItemContainerStyle>
    <Style TargetType="{x:Type MenuItem}">
        <Setter Property="Command" Value="{Binding}" />
        <Setter Property="Header" Value="{Binding Path=Text}" />
        <Setter Property="CommandParameter" Value="{Binding Path=Parameter}" />

        <Style.Triggers>
            <DataTrigger Binding="{Binding }" Value="{x:Null}">
                <Setter Property="Template" Value="{StaticResource MenuSeparatorTemplate}" />
            </DataTrigger>
        </Style.Triggers>
    </Style>
</ContextMenu.ItemContainerStyle>

Hope I got the syntax right - I don't have an IDE on this machine to verify the code

EDIT

Here is an example template for the context menu separator. I am putting it in ContextMenu.Resources, although you could put this anywhere you want in your application as long as the ContextMenu can access it.

<ContextMenu.Resources>
    <ControlTemplate x:Key="MenuSeparatorTemplate">
        <Separator />
    </ControlTemplate>
</ContextMenu.Resources>

EDIT:

My first answer to this question, though it actually worked, does not follow the MVVM design principle. I am now providing an MVVM approach and leaving the original answer below for reference.

You can create a behavior to solve this problem.

XAML:

<Menu>
    <MenuItem Header="_File" menu:MenuBehavior.MenuItems="{Binding Path=MenuItemViewModels, Mode=OneWay}">

    </MenuItem>
</Menu>

ViewModel:

public IEnumerable<MenuItemViewModelBase> MenuItemViewModels => new List<MenuItemViewModelBase>
{
    new MenuItemViewModel { Header = "Hello" },
    new MenuItemSeparatorViewModel(),
    new MenuItemViewModel { Header = "World" }
};

Behavior:

public class MenuBehavior
{
    public static readonly DependencyProperty MenuItemsProperty =
        DependencyProperty.RegisterAttached("MenuItems",
            typeof(IEnumerable<MenuItemViewModelBase>), typeof(MenuBehavior),
            new FrameworkPropertyMetadata(MenuItemsChanged));

    public static IEnumerable<MenuItemViewModelBase> GetMenuItems(DependencyObject element)
    {
        if (element == null)
        {
            throw (new ArgumentNullException("element"));
        }
        return (IEnumerable<MenuItemViewModelBase>)element.GetValue(MenuItemsProperty);
    }

    public static void SetMenuItems(DependencyObject element, IEnumerable<MenuItemViewModelBase> value)
    {
        if (element == null)
        {
            throw (new ArgumentNullException("element"));
        }
        element.SetValue(MenuItemsProperty, value);
    }

    private static void MenuItemsChanged(DependencyObject d, DependencyPropertyChangedEventArgs e)
    {
        var menu = (MenuItem)d;

        if (e.OldValue != e.NewValue)
        {
            menu.ItemsSource = ConvertViewModelsToFrameworkElements((IEnumerable<MenuItemViewModelBase>)e.NewValue);
        }
    }

    private static IEnumerable<FrameworkElement> ConvertViewModelsToFrameworkElements(IEnumerable<MenuItemViewModelBase> viewModels)
    {
        var frameworkElementList = new List<FrameworkElement>();

        foreach (var viewModel in viewModels)
        {
            switch (viewModel)
            {
                case MenuItemViewModel mi:
                    frameworkElementList.Add(new MenuItem
                    {
                        Header = mi.Header,
                        Command = mi.Command,
                        Icon = mi.Icon
                    });
                    break;

                case MenuItemSeparatorViewModel s:
                    frameworkElementList.Add(new Separator());
                    break;
            }
        }
        return frameworkElementList;
    }
}

Classes:

public class MenuItemViewModelBase
{
}

public class MenuItemViewModel : MenuItemViewModelBase
{
    public object Header { get; set; }
    public ICommand Command { get; set; }
    public object Icon { get; set; }
}

public class MenuItemSeparatorViewModel : MenuItemViewModelBase
{
}

Original Answer:

Or, instead of having your ContextMenu bind to a collection of commands, bind it to a collection of FrameworkElements then you can add either MenuItems or Separators directly to the collection and let the Menu control do all the templating....

<Style x:Key="DataGridCellStyle" TargetType="{x:Type DataGridCell}">
    <Setter Property="ContextMenu">
        <Setter.Value>
            <ContextMenu ItemsSource="{Binding Commands}" />
        </Setter.Value>
    </Setter>
</Style>

C#:

this.Commands = new ObservableCollection<FrameworkElement>();

this.Commands.Add(new MenuItem {Header = "Menuitem 2", Command = MainWindow.AddRole1});
this.Commands.Add(new MenuItem {Header = "Menuitem 2", Command = MainWindow.AddRole2});
this.Commands.Add(new MenuItem {Header = "Menuitem 3", Command = MainWindow.AddRole3});
this.Commands.Add(new MenuItem {Header = "Menuitem 4", Command = MainWindow.AddRole4});

this.Commands.Add(new Separator);

this.Commands.Add(new MenuItem {Header = "Menuitem 5", Command = MainWindow.AddRole5});
this.Commands.Add(new MenuItem {Header = "Menuitem 6", Command = MainWindow.AddRole6});
this.Commands.Add(new MenuItem {Header = "Menuitem 7", Command = MainWindow.AddRole7});

Just used this approach in my app - the separator looks better this way also.