I'm from your area - just north of Boston here, grew up in Marshfield. Been heading out west since 2014 so can give you some observations / stories. Definitely don't have it figured out though.
Where I hunted in Montana, Elk were much more in the timber with limited parks and openings where I'd see them at either end of the day, maybe. I had more luck there in Archery season where I could rely on calling and got one bull that way. No need for a spotter where I hunted, no need for a tripod, hand holding binoculars. More limited glassing. I would have come home with an Elk this year (Cow) if it wasn't for a scope failure, and they came out to feed about an hour before dark before I missed by a MILE. This year was my first trip to MT during rifle season. Ended up bailing to the breaks and shooting a mule deer before driving home (more on that later).
Where I hunted in Colorado I went for first rifle in the beginning to middle of October. Still some calling first and last light, Elk mostly in the timber, and crossing from private back to isolated tough to reach public. My strategy was a ~4 mile hike around the back of some private to intercept Elk coming off the private to bed in timber. There was much more glassing and patterning that hunt, but at the end of the day I ended up killing my bull "Eastern Style" - jumped a bedded herd and had to make a running shot in timber. Go figure, was anticipating the 300+ yard shot and it was ~50.
Wyoming has mostly been archery for me, but where I hunt transitions right into rifle in the end of September. Much more glassing and mixed terrain where the tripod and pan head paid dividends. If I hunted that area rifle season I would primarily be getting to a good vantage point, glassing, and angling for a longer shot. Naturally the only bull I got in WY was the opening day of rifle, about 5 seconds into legal shooting light, and I shot him 40 yards broadside off-hand.
Honestly, I agree with
@Matt Cashell - perseverance probably would have gotten me an Elk and maybe a bull this year and feels like the ticket to me in later seasons. But I was solo, having gear issues, under-gunned on shelter and sleeping bag, and freezing my a** off by myself and didn't want to get stuck up the forest road I was on. I wussed out and went deer hunting where I could stay in a motel. Being able to stick it out and deal with the cold better, glass and watch would have been the ticket. Lesson learned for my first late season trip, and it's going to cost me a LOT in gear upgrades to fix some mistakes this off-season.
If you're ever north of Boston and want to chat hunting - give me a shout. I try and head out west every year and I'm usually solo.