I’d second the brewpub. It’s the Bullfrog Brewery downtown. Very good beers…excellent wings. Try the "aftershock" sauce, sweet and spicy.

I have never been to these places, but my buddy from Williamsport recommends them.

Shamrock Grill – cheesesteak
Crippled Bear Tavern – Bear burger
Bridge Tavern – reuben
Park Pizza – sausage & pepperoni pizza
Sunset ice cream – hard ice cream

I should also mention that my friend says that the Crippled Bear Tavern is in a "seedy" part of town. I hope this helps and good luck!

The brewpub in Williamsport is actually very good. I was there last year at this time. All the Little League teams will be arriving this week for the World Series. If you can arrange to do so, I highly recommend a trip across the river to see one or more games while you’re there.