Pollyanna board game re-creation

Have you tried Inkscape or other design software? Except for the characters, each quarter of the board is the same so you can just design one quarter and copy and rotate to make the rest. The individual characters can be added after the board is made. Depending on how big you want the board, you may even want to make each quarter a separate piece with tabs and assemble each time you want to play. Look at this for inspiration Custom Harry Potter Monopoly Game Set. The best advice is to start and if or when you get stuck, come back here. I guarantee someone will help you out.

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