Wrap each date with one piece of bacon and secure tightly with toothpick.
Heat a non-stick skillet over medium heat. Add bacon-wrapped dates and cook until golden and crispy all over, flipping as needed, 6 to 8 minutes. Let cool slightly before serving.
Caramelized Onion & Maple Chutney
Melt butter in large skillet over medium heat. Add half of the onions and cook until they begin to soften, 1 to 2 minutes. Add remaining onions and continue cooking until translucent, 5 minutes. Reduce heat to low and cook, stirring often, until very soft and golden, 15 to 20 minutes.
Stir in maple syrup; continue cooking until sticky and caramelized, 6 to 8 minutes. Remove from heat and let cool completely. Store in an airtight container and refrigerate for up to 5 days.
To Assemble
Place caramelized onion and maple chutney in small bowls and arrange in central spots on the board. Arrange cheeses, bacon-wrapped dates, maple fudge, crostini, crackers and grapes to fill in any gaps.
Notes
Use amber or dark Maple from Canada maple syrup in the Caramelized Onion & Maple Chutney for a rich, robust flavour.