We are a commune of inquiring, skeptical, politically centrist, capitalist, anglophile, traditionalist New England Yankee humans, humanoids, and animals with many interests beyond and above politics. Each of us has had a high-school education (or GED), but all had ADD so didn't pay attention very well, especially the dogs. Each one of us does "try my best to be just like I am," and none of us enjoys working for others, including for Maggie, from whom we receive neither a nickel nor a dime. Freedom from nags, cranks, government, do-gooders, control-freaks and idiots is all that we ask for.
I am not talking about either hiking/walking on well-built trails where sneakers are fine or, the other extreme, technical climbing. The great in-between is what we enjoy taking on. Rugged hikes with steeps and some scrambling requiring fitness and hands and knees at times.
Some people claim Tuckerman's to the top of Mt. Washington is a great example of that sort of thing. Most outdoor people in New England have taken it on at least once.
Hiking is an all-weather sport. Our favorite hiking gear:
Pants: Prana and Montane Medium-duty hiking boots: Meindl and Vasque Light, layerable packable all-weather jackets: Many choices, but Patagonia way too expensive. Daypacks: Osprey Knee pads: Any cheap ones on Amazon. If you have bony knees, they are handy on rocks. Hiking poles: Glorified walking-sticks. Not needed for well-build trails but handy for rough hill hiking and useless on rocks. In Euroland, everybody uses them. On our Dolomites hikes we could have used them on scree slopes - everybody else did and they would have spared Mrs. BD some knee damage on the steep downhills. Ordinary LL Bean poles are fine. When there is scrambling, just stick them on your daypack. Most daypacks have pole-holders.
Check out the Skechers 'verdict' boot. Good boot and not expensive. Their 'workshire' boot is pretty good too.
Sox are most important. Good hiking sooks, not cotton, snug, padding on the sole can be a plus.
I usually break in my boots by getting them wet (walking up a river works) and wearing them the rest of the day. Take them off and leave them in a heated house for a few days.
I carry a 'go pack' with me when I hike. A Ziploc bag with a couple of paper towels folded, a small pack of nose tissue and a couple of individually packaged wet wipes.
A couple of various sized bandaids for blisters. A good water bottle or two if needed and a few water purification tablets. fire starting device (I carry a fero rod). a decent knife in addition to the pocket knife I always carry. Snacks. Telephone.
Because of recents incidents I have seen I now carry a tourniquet and compression bandage too.
I would stay far away from Tuckermans Ravine as long as there is snow on it... There are crazy skiiers that ski down the ravine and don't always stop when encountering hikers on the way up or at the bottom.
A friend and avid mountaineer had both legs broken by a skier on Tuckermans...