Tyler received a Melissa and Doug Money Set a couple years ago, and it has finally come in handy! I made a printable of a tree with the tree trunk having four spaces for four quarters. When you collected 4 quarters to make a dollar, you win! Hence, you completed the dollar tree!
Tyler and I played this together; it took 20 minutes to 1/2 hr. to play... But I can say, that we've played two times and he knows that when he has 5 pennies, he can trade them in for a nickel! And when he has two nickels, he can trade them in for a dime. Eventually, I can show him that 10 pennies is 1 dime, etc. But for now we are working on making nickels from pennies, dimes from nickels, etc.
Inspiration & other money games to check out:
Got A Buck? @ E is for Explore
The Trading Game: Money Style @ Spend a day in Second Grade
Counting with Coins @ Relentlessly Fun, Deceptively Educational
Money Bags: A Coin Value Game-- We have played this many times, but still a bit advanced for Tyler