They are literally the same, Madison just feels more high end.

Madison and Guilford are almost interchangeable but Madison inches out Guilford by a few hairs. They're both beautiful towns and you can't go wrong with either. Madison has a better youth sports program, better sports facilities - highschool sports are also more competitive. Madison has three town beaches vs. Guilford's one. Guilford has better restaurant options, a better downtown, and seems more down to earth than Madison. Madison is more snobby/stuck-up. I've looked at homes for sale in both towns for a few years and Madison has lower inventory and higher prices IMO

Guilford kids first cars were old Volvo wagons, Madison kids got old 3 series

That’s the only difference

Madison has better beaches, better youth sports facilities, and a brand new elementary school and community center in the works. Guilford has a new high school and better shopping and more restaurants/commerce. When I say “better” it’s not by much. They are very similar towns, and you won’t go wrong with one over the other. I would recommend walking around each down town and visiting the beaches (go to the Surf Club and Jacob’s beach) to see what feels best to you.

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Basically the same town, but I find the people in Guilford much, much more chill.

That and, at least, you don’t have “tall and handsome” Bob Stefanowski as a neighbor.

I love them both. Public schools in both towns are excellent. I haven’t looked up the mill rates in a while but I did get the impression Guilford’s are getting a little high. The vibe people are talking about is a thing, a littje, but both Towns tend to be gentle kind people or try to foster that.

The old saying in Connecticut is this:

“Guilford for culture, Madison for class, Clinton for clams.”

They’ve changed somewhat over the decades though. At one time Guilford was just cranking out amazing artists and musicians

I would happily live in either of them

Madison resident here. Like people have said, similar towns. Moved here about 2 1/2 years ago, but I grew up a few towns to the east. Both are amazing. The house we wanted most was in Guilford. I would have been ecstatic to move there. Great schools, solid sports, lots of outdoor activities. Guilford has more shopping and restaurants. Madison really lacking in the restaurant department. Guilford is more politically divided. The blues are bluer and the reds are redder. Madison used to be red town - old school New England GOP. That has faded and it's now centrist blue town. The high end in Madison, down by the beach, is higher end than Guilford, but that doesn't represent most of the town. Lots and lots regular people here.

The snobby reputation is a bit overblown. Growing up in less bougie town year ago, Madison and Guilford both seemed liked snotty rich towns. Living here now, I don't find that to be true. OK. Let me clarify. If you are a blue collar person who works on their car in your garage and runs the engine loud to blow it out during dinner time, you might have neighbors get an attitude. There are a few people, for sure. Probably the worst we encountered was a non-native who grew up in Waterford, married a doctor, and acted surprised that my wife and I, with our normal jobs, can afford the town. But that was literally one thing in over 2 years.

You can't go wrong with either.

EDIT: Taxes are a bit higher in Guilford. The gap will close a little once the bill for the school renewal and community center hit the budget. Should still be a bit lower than Guilford.

I’d vouch for this comment. The economic diversity in both towns is there, because until the pandemic hit, working class salaries could get you something for sure, in either town, even a couple of WalMart greeters could afford to buy something as long as they kept their eyes peeled. Sadly, the pandemic inflated house prices a lot here. Hopefully it won’t be permanent in terms of inclusion. The shoreline does not want to be Fairfield County.

Racial diversity is not big and neither town is happy about that so it would be better if we were more diverse.

I got in on the early wave, before things went crazy. 4br 2.5 bath, 1900sq ft on 2 acres for $365K. Coming from Boston, I couldn't make an offer fast enough. I could probably sell it for $500K now.

No but the whole state is stuck with the nitwit Lamont.

Madison is the equivalent to what Darien was like during the 1970s and 1980s. People walking about, waving to each other not afraid to stop for a quick chat, a bit of snob culture sprinkled in.

That’s a hell of a bargain considering what is even available for sale and now the prices for what you get. Well done!

Yeah, I got lucky with the timing. The wave hit Boston first. I made a killing on my sale up there and caught a bargain here. Fast $100+k I ever made😂

Guilford cops haven’t stolen lobsters sooo

Basically Saab vs Volvo…

They’re both very nice towns. I find people in Madison are a bit more snobby but overall you can’t go wrong with either.

Nerd

I grew up in Madison (graduated 2013) and had a friend group in Guilford, here's my honest assessment.

Madison is overall a better school system and might bode better with in state colleges. Madison oozes athletics and sports, is a bit richer and preppier. Vineyard Vines people.

Guilford seemed a bit more arts focused, almost more hipstery. There's a bunch of recording studios in Guilford, not so much in Madison. Still a similar type of person I'd reckon, but less stuck up.

At the end of the day either are more similar than different, Guilford being a bit cheaper from a real estate perspective. I can't say I enjoyed growing up there though.

Effectively no difference in the schools. Certainly not with perception for college admissions.

Fair. Madison ranks 16 in state, Guilford is right behind at 19. Definitely assumptions I made based on what I saw

Rankings like that don't matter for high schools like they do for colleges (and they don't matter much there either). US News and others just put put the rankings for clicks.

Very similar. Guilford is a little more spread out and laid back. Madison is a bit more preppy.

Madison has better beaches. Guilford is more rolling and scenic.

Ah, Volvo wagons. The official car of the New England academic elite.

Grew up in and lived in Guilford for 25+ years. This is spot on.

Madison has great beaches (surf club and Hammonasset)… and that’s about it. Most of the residents and NYC weekenders have big time superiority complexes who are judgmental and obsessed with social status. The amount of 16 year olds bombing around town behind the wheel of their daddy’s Mercedes or BMW is mind blowing. The sub par downtown area is saturated with boutique shops run by bored, waspy housewives. The police force has had their share of scandals, including (but not limited to) lobster poaching, cocaine and hooker parties, and pimping teenaged prostitutes for backseat squad car romps. One officer had taken issue with me dating an ex of his whom he had repeatedly physically abused. He would literally stalk both she and I, and use “thin blue line” intimidation tactics. It was made clear to me that, after reporting his erratic and inappropriate behavior multiple times, his supervisor was complicit and flippant about the situation.

The high school educational experience is objectively good, and sports teams usually perform well. But if you care to look at what has been swept under the rug, you’ll find rampant opioid issues and teen suicides. Don’t ignore the fact that, for literal decades, the DHHS football program has heavily promoted steroid usage among players. Diversity is nil, as Madison is whiter than a mayonnaise and wonder bread sandwich, and it seems that most residents prefer it that way.

Guilford and Madison share many similarities, though Guilford is dialed way, way back. People are more relaxed and friendly, and are seemingly less concerned with what street you live on, or what car you drive. There’s a bit more diversity, the downtown green is top notch, and the schools are good. The biggest police scandal has been whether or not they should relocate the “open to the public” department’s basketball courts elsewhere.

I have lived in six different towns in CT, and while Madison was probably the wealthiest and was seemingly the “best town” on paper, my personal experiences there were pretty terrible. Look at the time, my free therapy hour is up haha

Love your view. Ok so if not Madison (and let’s rule out Guilford for this moment…) WHICH CT down would you recommend?

Sorry for the diatribe haha Based on the 5 CT towns I’ve spent significant time in as an adult, I’d have to say West Hartford has personally been the best experience. There’s a good sense of community, people seem to be more accepting. It’s fairly upscale and safe, but lacks the sting of snobbery. There’s comparatively more racial, cultural, and social diversity, the schools are good, and the downtown/blueback area has a lot going on. It’s a great place to raise kids, as most of the neighborhoods are very walkable and are set up in a way that seems to promote social interaction. The town radiates with opportunities for kids to grow up well rounded and learn life in a safe (but not insular) environment

I’ve lived in Madison for 15 years and have two kids in the school system.

I honestly don’t think I’d give either town the edge on schools or quality of education. They are both excellent.

Madison has better athletics.

Guilford has a better green and restaurants and is a much more agrarian community.

Both towns have excellent public libraries.

Madison has much better beaches including hammonasset state park.

Guilford has better community events and a more community focused police force.

Madison has a country club if that’s your thing.

Home prices tend to be a bit higher in Madison.

Won't lie that is awesome, its like timing the market but you did not time the market.

I live in guilford and am a young person there so I am in the heat of the rivalry. I have friends in both towns. Madison is richer, and more preppy than guilford by a lot. I always thought it wasn’t that much of a difference until I learned that the madison high school’s cafeteria in actually more of a food court with food from actual restaurants or chains. Also the roads. I live right on the edge of guilford and I am not exaggerating when I say that just by the potholes you can tell when you cross into the other. Madison is rich and cares about looking rich. Guilford schools are better. we have more advanced classes and opportunities and also the high school is brand new and really nice. Honestly from what I can tell the sports aboie about equal. The guilford high school arts department is an a whole different level than madison. Huge, beautiful plays and musicals done every year and the music program is wonderful. There’s even a town band that a lot of the community gets involved in and really loves. Guilford people are much nicer, not just the teenagers but also adults are too. People are always waving and people walking their dogs or going for a jog down the street, and generally everyone is more down to earth. Madison is still a very nice place though. They have state parks including a few beaches and a really nice wooded park in north madison. Both towns are bigger than most people think too, especially guilford. Guilford and north guilford are one town, but very different. Also both towns are very liberal. You’ll see pride flags by and outside of stores, one of the madison churches just had “drag bingo” to raise money for the youth mission trip which was a huge success. You’ll never really see trump or confederate flags in someone’s truck. they are definitely very similar, but they are nice towns with beautiful scenery and solid schools systems.