I lived in Worcester for about 12 years. I left about two years ago, so I'm not currently up to date on everything, but I visited in October.

The Palladium usually has shows, and it's pretty central to the city (near the good end of Main st). There's a bunch of restaurants in that area that are nice. Plus that area is near other college kids, more specifically Worcester Polytechnic Institute. There likely won't be many students around at the time, but there will be a few. That area is going to be a decent place for you. Highland Street passes down through the college housing and past Elm Park which is pretty nice generally. It connects with Park Ave.

There's also a disc golf track across from Elm Park that's a nice hike. On that street there's a ton of restaurants and bars. As well as an awesome comic/toy shop (That's Entertainment). Definitely check out that street. One of my favorite places to get fried chicken is on the corner of Park and Chandler st, called BT's.

From there head up Chandler towards Main st, and you'll find a bunch of ethnic places to eat, like Africa/Jamaican. It's busy and that street sucks to drive on, and the pedestrians are fucking morons so be careful!

There is also Water St, which has a bunch of bars and restaurants. I don't know what's there anymore, but there's a ramen place. Near the end is Wings Over Worcester if you want late night, drunk chicken decent. Again, there's a bunch of bars, and good night life. Not sure how comfortable you feel being out at night, but it can be intimidating, as the area isn't the safest, but I only ever had one issue in the 12 years I was there, walking the streets after like 11pm. It's relatively safe if you're not an idiot.

You cn also head up Shrewsbury st, where there again are a bunch of restaurants. Great dinners on that street. That will bring you across the bright and out towards Shrewsbury (the town). There's a bunch of stuff out here as well. Definitely worth going out that way. That's route 9 and it will bring you all the way to Natick and Boston if you keep following it. There's a "fancy" mall in Natick, and again a lot of food.

There is also Union Station which will take you into Boston. Definitely worth hopping on the Trai. And checking out.

DO NOT DRIVE IN BOSTON. It's worse than NYC and it fucking sucks. It's a maze. Take the train and walk. Get an Uber while you're there if you need it, but avoid driving. The city is cool as fuck though.

As far as public transit, the public bus has always been solid. I took it for years while I was going to school for my associates and it may run late a few times, but it does well. I took ubers a lot there, and if you plan on going out drinking, take them. I only had an issue once in like 5 years I took them. Theyre great. Over all though, it's a very walkable city, but biking is very rough because there's a ton of hills.

Theres a ton of stuff to do there. Go on adventures, and even just walking around will lead you to something cool!