Well, it kind of depends. You don聮t say anything about hiking in the snow. But you are in New England. So I shall assume you are doing some hiking when the weather is fairly decent. That lets me take a middle-of-the-road approach.
Vasque Wasatch GTX Boot
Vasque Wasatch GTX BootI think you need a pair of mid-weight hiking boots with some after-market things added for more warmth. Take a look at boots such as the Wasatch GTX ($170). They have waterproof nubuck leather uppers, plus Gore-Tex liners. They聮re not real heavy but are great for both day hikes and backpack trips. 聮s Civetta ($240) has similar features in a boot that聮s a little beefier and better for real sloppy conditions or heavier loads. Same for the Escape GTX ($235).
You can add warmth to any boot in several ways. For starters, wear a pair of light liner socks, and then layer on some mid- to heavy-weight wool socks such as Expedition Trekking Socks ($18). You also can try neoprene socks聴 sells a pair of 2mm neoprene boot socks for $12.
For outside the boot, don a pair of Crocodile Gaiters ($60) to ensure snow and water don聮t get into the tops of the boots.
That setup should keep you reasonably warm in cool to cold weather. But if you聮re out for extended periods of time in snow and ice, you will want an upgrade. Get some light mountaineering boots; Glacier EVOs ($265) are great. I am less enamored of the various 聯winter hiking boots” several companies put out. I think they are too soft for good ankle support. But you might take a look at the Deemax Dry Boots ($130), which are waterproof and insulated.
The is now online so you can get prepped for gift-giving season聴even if everything you pick is for yourself!