Well, it kind of depends. You dont 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.
I 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 Vasque Wasatch GTX ($170). They have waterproof nubuck leather uppers, plus Gore-Tex liners. Theyre not real heavy but are great for both day hikes and backpack trips. Zamberlans Civetta ($240) has similar features in a boot thats a little beefier and better for real sloppy conditions or heavier loads. Same for the Scarpa 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 SmartWool Expedition Trekking Socks ($18). You also can try neoprene socksCabela's sells a pair of 2mm neoprene boot socks for $12.
For outside the boot, don a pair of Outdoor Research Crocodile Gaiters ($60) to ensure snow and water dont get into the tops of the boots.
That setup should keep you reasonably warm in cool to cold weather. But if youre out for extended periods of time in snow and ice, you will want an upgrade. Get some light mountaineering boots; La Sportiva Glacier EVOs ($265) are great. I am less enamored of the various 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 Salomon Deemax Dry Boots ($130), which are waterproof and insulated.
The 2009 Winter Outside Buyers Guide is now online so you can get prepped for gift-giving seasoneven if everything you pick is for yourself!