I have horrible teeth (thanks, mom) and a lot of dental trauma and anxiety. I’ve been seeing Dr. Tagliarini at Comprehensive Dental Health in New Haven for at least 10 years, and would recommend to anyone with dental anxiety. He is very gentle and understanding. Crystal and Des are the people to work with at the front desk. I do think he could’ve been more proactive with preventative care. I have had a few failed root canals and I don’t know if it’s just my crappy teeth or if maybe I should’ve gone to a specialist. But overall I’ve had positive experiences. The office recently merged with a larger group and I can’t speak to the quality of the other dentists, and I see some negative reviews online, so ymmv.

Nah, half the cars here have FL plates, you’re good.

I’ve heard good things about Seabury Hill realtors.

Guilford, Madison, Old Saybrook, Niantic / East Lyme have cute downtowns and beaches. Niantic has The Book Barn, a large used book store with multiple buildings / locations and a boardwalk. Madison has RJ Julia bookstore. Many town beaches are free during the off-season and I believe Hammonasset is free for everyone right now including non-residents. Seaside State Park in Waterford is cool, it’s an old sanatorium right on the water.

Lots of nice towns outside of the city. Mostly suburban with small downtown / commercial areas. Very family-oriented, great schools, safe, clean.

I recommend Milford and Branford. West Haven and East Haven aren’t as nice as Milford/Branford, but less expensive.

I would also look into Hamden, Stratford, North Haven, North Branford, Guilford, Madison, Clinton, Westbrook, Cheshire, Orange, Woodbridge. Some of these towns are $$$.

I would avoid the Naugatuck valley towns (along Rt 8). MAGA country.

Fyi, the traffic on Rt 95 is pretty bad. Rt 91 isn’t as bad imo but depends on the time/day. Lots of backroads, but they get traffic-y at rush hour and after school. Employee parking at Yale can be pricey, and sometimes there’s a waiting list for the most convenient lots. Yale has a free shuttle but it only covers East Rock. The public buses are decent for such a small city. There is also commuter rail (MetroNorth, Shoreline East, and the Hartford Line).

Eta: just a heads up, property taxes in CT can vary greatly between towns, as each town has its own mill rate. New Haven has very high tax rate because a huge portion of the land here is non-taxable non-profit or state property so the burden falls on property owners. We don’t have county government here, so no county taxes.

https://portal.ct.gov/OPM/IGPP/Publications/Mill-Rates

Beaver Hills is the best bang for your buck. Only problem is that it’s gotten expensive the past few years, there’s very little inventory, and it’s hard not to get outbid by large landlords. But that’s pretty much every neighborhood in New Haven these days.

East Rock and Wooster Square are always recommended, and both are quite lovely but also very expensive, although you might be able to find an affordable-ish condo. Westville is also very nice but still pretty expensive. Fairhaven and Fairhaven Heights along the Quinnipiac River is nice, more affordable, very old houses. Edgewood can be hit or miss, but I would still consider it. Morris Cove / East Shore is affordable, safe, and by the water, but it’s a little isolated from the rest of New Haven. It’s also where the expanding Tweed Airport is located, and there are more homes available there than other neighborhoods because of the airport. Amity (by Westville) is affordable. Downtown is mostly expensive condos but it’s convenient and extremely walkable.

I would avoid: Newhallville, The Hill (except City Point area), West Rock. I’d be cautious about Dixwell, Dwight, West River, The Annex.

In neighboring town of Hamden, Whitneyville is safe and not too expensive.

I highly recommend checking out the CT First Time Homebuyer Program. Even if you’ve owned before, a lot of the rules are different for New Haven, because the city is like 70% renters and they want to increase homeownership. Don’t sleep on that Yale home ownership money either.

https://www.chfa.org

Moved here from Somerville, but I was older (early 30s). It was a smooth transition. New Haven has a lot of what a bigger city offers - dining, nightlife, culture - in a smaller, more affordable, and easily accessible package. Architecturally, it’s quite beautiful in some neighborhoods like East Rock and Wooster Square.

Parks, community greenspaces, community gardens.

https://uri.yale.edu/programs/greenspace/groups

https://www.newhavenct.gov/government/departments-divisions/parks-and-public-works/parks-trees/our-parks

https://gathernewhaven.org/our-programs/community-gardens?amp

The Barberie. Geo is excellent, has done a great job shaping my hair when it’s really overgrown. He used to work at Skull and Combs, I followed him to his new place. But the owner does both barber and longer cuts so she’s a good option too. Very chill atmosphere.

https://www.thebarberiesalon.com

I’ve also had good luck with Octavious at Pro-Style. More of a fade / simple cut place, but he also shaped my overgrown hair well. Very experienced barber.

I have lived in: interior CT, western MA, Boston area, and coastal CT over the course of 40+++ years.

Interior CT - more humid in summer, snowier, colder

Western MA - snowiest, coldest, same humidity

Boston - cold, snowy, urban heat island

Coastal CT - milder, fewer extremes, less snow, rains when it snows elsewhere, windy, late falls, cool springs (warmer springs inland), less humidity in summer.

Mostly outdoor stuff. Tubing and kayaking/canoeing nearby in the warmer months.

Eta: Brewery Legitimus in New Hartford.

Depends on their interests. I remember it being pretty boring being a teen in the Hartford area. That’s a tough age gap in some ways - about the same as my sibling and I. It’s like one is too old and the other is too young, and it’s hard to find things that would be interesting to both.

We have some cool outdoor places to explore. The rail trail along the CT River is fun. If they’re into hiking, look at some the land trusts in the region.

You could drive or take a train to New Haven. Walk around Yale campus, walk through the free museum, grab some food, check out some stores. Go to Edgerton Park, check out the free greenhouses. The older brother might like Strangeways. New Haven feels more like a city and I loved that stuff as a kid.

Alternately, head north to Basketball Hall of Fame, or maybe check out Northampton, Easthampton, Amherst.

Or check out Mystic Aquarium.

It’s more about assuming ALL people of color live in poverty.

Worth noting that CT is one of the safest states in the country.

Yes! This was going to be my comment. It throws people for a loop.

Just fyi, OP - most of the towns recommended here have high housing costs. If you’re looking to rent, be aware that these towns consist of mostly single family homes with low density zoning, and there aren’t many apartments. Also factor in commute and cost of parking. Indeed, these are some of the best districts in the state, but also CT has some of the best public schools in the country, and most districts offer a very good education.

If you’re looking to stay close to campus, then East Rock has tons of young families. Many are Yale-affiliated. It’s nice to be able to walk your kid to school and then walk or take the free shuttle/bus to work. Westville is also popular with families. It’s a little farther from Yale, but New Haven is a very small city, so it’s not a long commute, with a couple of bus lines if you don’t want to pay for parking.

I’m late to this, but highly recommend Octavious at ProStyle on State Street. One person operation so he’s often booked, but he offers walk-ins on Tuesdays and Saturdays during certain hours.

Especially these days. Feels like there were more options pre-pandemic. I’m frequently in NYC and even there, some places have reduced their hours.

Grew up in Collinsville and highly recommend. It is a little far from the highway but otherwise it’s a lovely area. Love the history of the area, the rail trail, access to nature, local farms, all without feeling too rural. Lots of historic homes, and a lot of older homes (50s-80s) that are more affordable than the newer mcmansion developments, although they might be a bit small for a large family.

I also recommend the Unionville section of Farmington and Weatogue section of Simsbury. Affordable areas in really nice towns.

I haven’t been in years, but DAR state forest has a wildlife blind overlooking a beaver pond. Not sure how active it is now. But I’ve had good luck with wildlife blinds. Also go at dusk or dawn. Good luck!

The one in Beaver Hills has definitely improved traffic safety. Witnessed a lot of accidents there before the roundabout was put in. Now occasionally someone will misjudge and hit a curb or a sign, but better a minor one-car accident at slow speeds than a multi-car accident at 60 mph. Still a lot of work that needs to be done to slow speeds approaching the roundabout, but it’s been a major improvement imo.

Eta: the bike lane in BH also need work, same with pedestrian crossings.

Great ideas. Lovely area with lots to explore.

OP, there’s a rail trail in Turner’s Falls that will give you some cool post-industrial and waterfall views. Awesome French King Bridge views on E Mineral Rd. Keep heading south to the Montague Book Mill - really cool used bookstore by a waterfall. Montague Plains Wildlife Management Area is a really interesting and unique landscape.

Grew up supporting the Hartford Whalers (left in 1997 to become the Hurricanes).

Traditionally Connecticut has been split between Boston and NYC teams. People in New Haven tend to support NYC. I grew up in northern CT and my family supported all the Boston teams.

Definitely check out some of the college games. Yale and Quinnipiac are usually pretty good, and Ingalls Rink is a neat place to catch a game (it’s known as “The Whale” due to its architecture). Other good college teams in the region as well. The minor league teams (Hartford Wolfpack, Bridgeport Islanders) are fun to watch, too.

Eta: it’s really easy to take the train into NYC and see a game at Madison Square Garden.

Sorry to hear that, definitely keep pushing. Good luck!

Lots of little towns with downtown / Main Street / central business district areas that could handle more density. I’m not talking condos, more like small starter homes on small lots.