I like living in Wilmington, it's a very pleasant city. The homes here are expensive, even by Massachusetts' standards, but in my opinion, the cost of living is worth it. Boston is pretty close which opens up a lot of possibilities when it comes to work and school. There are a lot of young professionals and entrepreneurs in the area. If you fall in that category or you just finished school and are looking for a career, you will have a lot to choose from in this area.
Wilmington doesn't have a whole lot of stores and restaurants to choose from, but it isn't too bad. There's a downtown shopping area with some nice places, which is probably the best area in Wilmington. The winters here can also be pretty fun because you will be close to a bunch of different ski resorts. The summers are mild, so if you enjoy staying active then you will always have something to do.