Hey lookinforahome, welcome to my side of the tracks.
Springfield can be rough. It's sometime overplayed, but it can be rough. There's actually quite a bit to do there though. Nightlife is O.K. (a bit more expansive and diverse than what's in Portland, but a it's a little bit less laid back too)... Worthington Street is the nightlife district in Springfield. It's fun on Friday and Saturday. Again, it's a little "tougher" than the Old Port in Portland, but I enjoy the wider variety of bars and clubs (Theadore's Blues Cafe is a lot of fun... even if you're not a blues fan. I'm not). Bring some friends and use common sense, you'll be fine and you'll probably enjoy it. Springfield is not as pristine as Portland, but few places in New England are. There are neighborhoods to avoid, but Worthington Street and the Downtown area aren't terrible.
Aside from nightlife, you do have Six Flags, good shopping, the NBA Hall of Fame, and some good cultural attractions. You can absolutely stay entertained.
Northampton is a lot of fun. It's really cool and you may spend a good deal of time there. It's a charming little area and there's a lot to do. Good restaurants, bars, etc. It has an excellent downtown, you won't want to miss it. THere's an old railroad tunnel that's actually a restaurant now. It's one of the quirkiest places I've been to. Check it out:
Union Station Restaurant
Westfield is a small school, but everyone I know that goes/ went there loves it.
You enjoy cities and have an appreciation for ones that don't necessarily have the best reputation. In that sense, you'll like Springfield. Downtown is cool... you'll see that it's oozing with potential. It has a nice skyline for a pretty small city. It's also built in a different fashion than a typical New England city (some density downtown, more sprawling outside the core). I like Springfield. I like Worcester, Providence and Hartford better (for comparably sized cities), but Sprinfield is cool. It's cooler than a lot of people give it credit for.
If you enjoy older industrial towns, be sure to drive through and check out Holyoke and Chicopee (during the day probably). While the towns are struggling without a doubt, there's some cool old architecture and integrity left. Holyoke reminds me of a larger Biddeford, actually. The old mills that dot the river are pretty impressive. I actually like the old mill housing too. Of course, now it's slummy since manufacturing has left the region, but the buildings are mostly in tact and quite cool. You'll also be close enough to check out Pittsfield and North Adams which are both cities that are beginning a rebound from tough times.
Hartford isn't too far away either and that's a city with some incredible architecture (and unfortunately, another that is struggling). You should take some trips and explore Hartford... it's a really cool town.
In the end, use common sense. I know from reading your posts here and archboston that you enjoy cities and everything urban. There is a LOT to explore in the Pioneer Valley in the way of cities and urbanity. Springfield, for all its flaws, has some fascinating things to see and do; especially for someone with your interests. I wouldn't recommend Springfield as a top destination for someone looking to start a family, but for a college student looking to explore some new cities and have a little fun, the Springfield area can offer a good degree of that.
You're like me in that you appreciate certain things about places that people often see through (like our mutual admiration of Biddeford, ME). You will find a lot of that in the Springfield area. I think that after some time there, you'll find that the harshest descriptions of the Springfield area are a bit overblown. It can be a real good time, especially for someone like you who appreciates the subtleties.
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Westfield and Springfield
try westfield, west springfield or southwick or holyoke
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