[NewJeffCT]

Originally Posted by whattodowhattodo

I lived in Madison for about a year until recently moving to Guilford. I'm not particularly familiar with Woodbridge, but I'll comment on Madison vs. Guilford.

Both towns have really good schools. Based solely on the numbers, Madison has a slight edge over Guilford. In my dealings with both districts, the staff have been really helpful and communicative. Since you have an almost 5 year old, I think it's important to note that as of the last time I checked, Guilford does not have a full day kindergarten. I believe that full day kindergarten was approved in the budget, but I don't know if that's going to start this coming fall or the following year. Madison has a full day kindergarten.

They also both have very nice town beaches. Surf Club Beach in Madison is definitely my preferred beach since it has a fantastic playground for young children (I have a 4 year old), although Jacob's Beach in Guilford is also good. The real benefit of Surf Club Beach over Jacob's Beach, if you have a young child, is that there is a nicer view of the beach when you're on the playground area (the kayak and whatnot storage kind of gets in the way at Jacob's Beach). Surf Club Beach also has a concession stand, although I've never eaten anything from there because we always bring food and snacks with us. Both beaches have picnic/grill areas.

Guilford's library has a great children's room whereas Madison's library is much smaller. Both have wonderful library staff and there's always the benefit of having access to Museum Passes (if you don't know about this, check into it...great way to get discounts/free passes to museums, the zoo, etc.).

As for shopping, even though Madison has a Stop & Shop, we were constantly driving to Guilford to shop at Big Y since we typically got better deals there. Guilford also has other stores, including a relatively small Walmart (relative to other Walmarts, that is). For other shopping, neither town has a large selection of stores. We ended up going to neighboring towns for this (Clinton, Branford, Hamden, etc.).

I've gotten the impression that Madison's population is a bit older than Guilford's, but City-Data.com says that the median age is the same so maybe it's just who I've come across.

Guilford has a large town green that is the center of town. Madison's town green is smaller and has an odd location right on Boston Post Road. In large part because of the location of Guilford's green, Guilford has a very charming small town feel to it. I know others feel differently, but in my opinion, Madison lacks a lot of the charm that Guilford has.

I would also consider Branford, which is very family-oriented as well.

Good comparison - reputation awarded.

[Stylo]

Woodbridge is actually the wealthiest. You will get a little uppiness as it's one of the wealthiest towns in the state. You'll also get some down to earth people too. Why not Orange? Generally more rentals, same school system, and more middle class than Woodbridge.

Woodbridge itself is basically 2+ acre lots and woods, with a very small commercial area at the edge of New Haven in Amity. You'd be going to New Haven and Milford/Orange for shopping and dining.

Have you looked at what $2500 gives you in the various towns? Again, places like Branford, Wallingford, Milford generally have more rentals especially at your budget. They are good towns with good elementary schools and unless you're going to be staying somewhere for an extended time (5+ years) I wouldn't discount any option.

[poodlecamper]

Daughter lives in Guilford, has a 5 year old boy, absolutely loves the town, great stuff going on all the time. There's a lake and a beach/playground for residents only, schools are good

[AnonChick]

I'll swing my vote for North Haven or Wallingford (no surprise, right?).

Both have a town green layout with a good mix of older and newer homes.
Both have apartment complexes that accommodate small families with plenty of parking.
Both have quick, easy access to the main commercial thoroughfares.
Both have family-friendly, safe neighborhoods (comparatively speaking - they're both suburbs with rural borders).
Both have good school systems.
Wallingford has the lowest utility rates because they own their own electric company.
Both give you more "bang for the buck" than the shoreline towns for rentals.
Both let you get to New Haven with your choice of two different highways (I-91 and Rte 15).
Both have walkable neighborhoods.
Both have that "neighborly" feel to them, unpretentious, comfortable but not disheveled.
Both have some pretty awesome parks and recreational facilities.
Both, now, have urgent care facilities and easy access to the hospitals in New Haven and to Midstate in Meriden.
Both have excellent fire and police departments.

[kidyankee764]

I'll second those who suggested Branford. It's extremely close to New Haven, has a stunning shoreline (look up Thimble Islands) and has a very nice, active town center.

Woodbridge is nice but it's a bit quiet and woodsy. Madison and Guilford are beautiful towns as well, and I highly recommend them. They will be a bit further to New Haven, though.

[leavy]

We moved to Guilford two years ago and I love it. We were torn between Guilford and Madison because of the schools. Someone from Guilford said: " Madison has the nicer beaches, we have the nicer people ". We found a great house in Guilford and I am happy to be here. The schools from elementary, lower and upper middle, and high school are great. They are building a new high school right now. The music program in the schools is outstanding, I don't know if that will turn out to be important for you, it hit me a bit as a surprise it was for us . Guilford is a close drive to New Haven. I would pick Guilford again

[JGBigGreen]

I'll also put in a pitch for Wallingford. My family and I moved here from Vermont about 6 months ago and could not be happier. The folks on this board were so helpful in our search and we had some similar towns on our original list. What each person will like in a town is so subjective but here is what sold us on Wallingford: proximity to both New Haven (my job) and Hartford (where my wife was looking for work at th time,) good schools, a "New England" feel to the part of town we chose, a stellar library, great rec programs, good rental options, lower tax base than many other New Haven area suburbs and the Wallingford electricity rates (I never thought an electric company would be a selling point for where I'd live!)

After half a year, we are thrilled with our choice. Commuting to New Haven is a breeze for me with traffic being an issue in very rare instances. (Hartford commute is a different story!) The YMCA in Wallingford is a gem, our sons are very active in the rec leagues, the schools are far better than what we were used to in Vermont (I think CT schools in general are some of the best in the nation but I'm far from an expert.) One of the things that sold us on Wallingford over North Haven was the extensive sidewalk system on the east side of town. With the nice weather, our sons are able to bike to the library, YMCA, parks. North Haven didn't feel as walkable or bikeable to us when we looked.

The great news is there are so many wonderful towns in the area that I don't think you can go wrong once you find the right fit for you and your family. Good luck with your search!

[NewJeffCT]

You'll also have to think about for how long you'll be renting. If you're going to be renting only for a year and then moving again, any of the towns mentioned above should be fine for a year. However, if you want to buy in a year or so (say, for the school year starting in September of 2015?) and don't want to change school districts, I'd suggest sticking with Woodbridge, Orange, Cheshire, Guilford and Madison. While North Haven, Branford and Wallingford schools are fine, they definitely are not as good in terms of test scores and percentages of kids going on to college as the first five.

[Meganbw]

Thanks so much everyone. So, here we are. We have a possible rental in an updated house but on a kind of busy street in woodbridge, and a similar house, maybe less updated, and not on a busy street in Guilford. Can anyone steer us in either direction? My heart says Guilford but I know a lot of that is due to the street issue and woodbridge being more of a mystery in terms of vibe.

[Stylo]

It's up to personal preference. I would personally go Guilford, but that's me. Woodbridge is more upscale, smaller. Guilford has a really great mix of character and coastal beauty. Woodbridge is popular due to location, an easy commute to Yale and the hospital, schools, and also being closer to FFC/NYC and closer to population centers. If Guilford's location works for you, that would be my personal choice.

Does a great town center, historic charm, and a beautiful coastline matter to you? If not, Woodbridge is just as good of a place to live - and has a bit of an edge on access to amenities.

You are just renting so I would pick the town you see as a long term commitment vs being swayed by specifics with the rental itself.