I grew up in Assonet. It's a great little town, but I'm not sure it fits the bill of what you're looking for. If any of those fit, It's going to be Westport, Fairhaven, and SOUTH Dartmouth (not N. Dartmouth).
Westport is a beautiful town, but it's the most rural of the ones you mentioned. It has a nice little village around the harbor and some fantastic beaches (I'll Post a pic below). It has a great winery (
Westport Rivers Vineyard & Winery, Westport, Massachusetts ) and a nice local microbrewery (
Buzzards Bay Brewing, Westport, Massachusetts ). There are a few good restaurants (Back Eddy, Bittersweet, etc) but not too many-- you'd have to drive out of town for the best. The school system in Westport is really bad; it's by far the worst of the towns you mentioned.
Dartmouth is a good town, but for the more interesting parts, I'd advise staying in South Dartmouth (near Padanaram Village). This is a very lively place and parts of it are exclusive (Tea Leoni and David Duchovny have a place there) but others aren't. It's a pretty diverse community. There is a decent sized university in town (UMass Dartmouth) and some nicer restaurants (Black Bass, the ORIJINAL Not Your Average Joe's, Wasabi, etc). The schools are good here if that's important to you. It's also right next door to New Bedford which has a lot to offer. I'll explain later on.
Fairhaven is a nice town, but it's on the sleepier side. West Island (don't worry, it's connected by a causway) has some of the most affordable ocean front housing in New England. It's also close to New Bedford and is really a bedroom community of that city. Schools aren't bad here either (in fact, Fairhaven High is an architectural gem).
In terms of diversity, shops, restaurants, these towns don't have a TON to offer on their own (Padanarum Village in Dartmouth being an exception). The are right next to New Bedford which, in My opinion is one of the best kept secrets in Massachusetts right now. The downtown area offers a great array of bars, clubs, restaurants, shops, etc. In fact, it's really well known for its seafood and Portuguese food due to the size of the fishing fleet (it's the highest grossing fishing port in the nation). It's a beautiful area (16 blocks of cobblestone streets are part of the Whaling District National Historic Park). There are some great art galleries and museums, a whaling museum, an Ocean Explorium, and some historic buildings and houses are open to the public. There's also a Symphony Orchestra and a fantastic theater (Zeiterion Theater). If you want to see some pictures, I have posted some on the last page of the photos of MA thread in this forum (here's the link:
//www.city-data.com/forum/massa...-their-10.html ). I wouldn't advise living IN the city (except the West End) due to the fact that the schools and residential services are better in the towns you mentioned, as well as the crime being a bit lower (it's not terrible in New Bedford, btw). Be sure to check out downtown New Bedford when you visit as this is the center of activity for the region.
In any of these towns you're still not too far from boston and you're particularly close to Providence RI (about 20-25 minutes). Newport RI is also a great town nearby.
Can I ask, what made you choose that area? It's not all that well known. I think it's a great area if you pick the right place to live. Hope this helps a bit.
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