Some people hatch and raise chicks year round. Winter can present more challenges but what matters is the temperature in the brooder, not the outside temperature. You are much more limited by your facilities and set-up than the weather.
I have a permanent brooder built into the coop so the chicks are never in the house after I take them out of the incubator. I have really good draft protection and generally just heat one area, letting the rest cool off as it will. When the overnight temperatures get down in the 30’s or maybe 40’s, I do cover it up better to keep it warmer. It helps for them to have some warm bedding to snuggle down into also. It needs to be warm enough for them to go get the water and food but that is not as warm as a lot of people think. A broody hen does not warm the entire universe. She just provides a warm spot for them to go back to when they get chilly. A broody can raise chicks in pretty cold weather. I have not done it myself but there are some photos on this forum where a broody has her chicks out walking on snow. My chicks spend a lot of time in the cooler parts of that brooder.
You are also planning on only having a couple. I always have a lot more than that. They can help keep each other warm by snuggling together in the bedding. With just two, they won’t get a lot of warmth that way.
Last summer when we were having out hot spell, I turned the daytime heat off at 2 days and the overnight heat off at 5 days. I don’t know what the temperatures were inside the brooder, but outside daytime temperatures were well over 100 and nighttime temperatures were in the upper 70’s, lower 80’s. I watched the chicks and they told me they did not need any additional heat by their actions.
That guideline of 90 degrees the first week and drop it by 5 degrees a week is a guideline. If you follow that you will be OK even with a real crappy windy brooder. That guideline like most guidelines given on this forum and even by the hatcheries on how to care for the chicks are just guidelines, not absolute laws of nature. We keep chicks and chickens in all kinds of different conditions, some a whole lot better than others. Those guidelines are meant to keep practically everybody out of trouble even if those conditions are not ideal. You have to have them for people that don’t have a lot of experience with chicks and chickens but they are overkill for most of us. What I strongly suggest when raising chicks is to provide one small area in the brooder warm enough by those guidelines and let the rest of the brooder cool off lower than that temperature. That way the chicks can find their own comfort zone. Mine normally play all over the brooder, just going back to the heat when they need to warm up. They normally sleep in a pile fairly near the heat source.
When the weather is colder I don’t turn the heat off after a few days. It varies by the time of the year, but in the cooler months I often keep heat on for 5 weeks, day and night. Remember that heat is just one small area, not the entire brooder. By providing heat in one area and allowing the rest to cool off way below those guideline temperatures mine get acclimated to colder temperatures. They feather out faster and thicker. I have taken chicks at 5 weeks from my brooder and put them in an unheated grow-out coop when the overnight lows were in the mid 40’s Fahrenheit. That grow-out coop has great draft protection but good ventilation up high so it does cool down a lot but a breeze is not hitting them to give a wind chill. I have had the overnight low hit the mid 20’s when they were 5-1/2 weeks old. They were fine.
I had about 20 chicks in there to help keep each other warm, they were acclimated, and they were regular dual-purpose chicks, not the fancy Silkies or other breeds that may feather out differently.
I don’t know when the temperatures will truly turn cold in Connecticut. It’s mid-August. I’d think yours will be OK from a weather viewpoint if you start them soon, but it really depends more on your facilities and how you manage them than anything else.
I don’t know what your coop and run look like, but at those ages, I’d give integration more thought than temperature, especially if your coop and run are fairly small. With snow, they may be crammed into a fairly tight space while they are still pretty young. You need extra space when you integrate. You can brood them, it just may take a bit more effort.
Good luck!