The Sole Proprietor is great. My wife and I like to go there for special occasions.
There is a great tapas bar called Bocado and a Mexican tequila bar called Mezcal. They are owned by the same people I believe. They are both a bit more upscale than the average place in Worcester, but nothing to crazy. Both offer valet parking which is good because Bocado, while it is a great place to eat and drink, is not in the best part of town. I would not recommend parking just anywhere. Use the valet as they have their own lot which they keep a close eye over.
Mezcal I have only been to for drinks and apps. We went for my birthday, but the wait for a table was over two hours. We found a spot at the bar and ordered their guacamole sampler which had three different kinds (delicious!) and I got a few tequila flights. They have a very large tequila selection and I was turned on to one in particular which has become my drink of choice.
Another great place is One Love Cafe. It is a little Jamaican place run by a super nice woman who treats you like family. The place is very small and it is a very laid back slow atmosphere there. Only go there if you are not in a rush, because they work on island time there. It is well worth the wait though if you like Jamaican food. The goat curry is my favorite thing I have had there so far, but I have yet to taste something there that I did not love. There is a food co-op right next door where they get a lot of their food from. That area of town looks a little shady too, but I do not think it is. i have never had any problems in that area so don't let looks fool you.
If you like meat, and lots of it, then check out Pampas Churrascaria. It is a Brazilian BBQ. The meats there are fantastic and they have excellent side salads to go along with it. Only go there if you are really hungry and love meat though. Pampas Churrascaria is just behind Shrewsbury St on which you will find a ton of great places to eat.
Dino's Ristorante Italiano is fun for Italian. they have really interesting dishes. I was there last weekend and had a veal and crab dish in a seafood sauce that was out of this world. They also have excellent pizza.
That should get you started at least. if you have not already, you might want to check out yelp.com. That is where I found out about a lot of these places initially. There are great user reviews and you get a good idea if it is the type of place you would like.
There are also a lot of great places to eat in the Worcester suburbs, but that is another post entirely
