You may be bit confused. North road is paved and in fine shape. Hogan road which turns off of North Road is a privately maintained logging road, it was used to upgrade powerlines last year so it received some maintenance. Not sure how this past winter treated it. There is zero parking at the trailhead. There used to be parking across from the hydrostation (note not the one in Shelburne you pass on North Road but another one upriver) (I havent been by there for several years). That said you can park just off RT 16 immediately under the railroad trestle and take the pedestrian bridge over the river (note some dogs really hate that bridge as its got steel grating). For the next week of two you can head up a steep hill to the ATV trail and follow it until you cross the river again. Then take a right immediately after the far more dog friendly bridge. Follow the blazes and the bike trail through the woods and eventually come out on road adjacent to a powerline. Follow the road along the hydro canal and you will come out at the Mahoosuc trail head. If there is ATV traffic (starting soon), dont go up on the old railroad bed, follow the road (ignore AMC trail sign) and follow it to the hydrostation (its fenced in), take a left on the road along the hydro canal until you come out at the second bridge. This keeps you and the dog off the ATV trail (not a pleasant place to be during ATV season as its dusty and noisy). It adds about 1.3 miles one way but its easy walking. Note the woods along the river and much of the Mahoosuc trail are loaded with ticks.
The short spur to Mascot Pond is worth it. After the Mascot spur you will eventually cross a dirt road, if you walk south (right) about 200 feet to a clearing and look carefully to your right there is path that heads into the woods and climbs steeply. Once on top you are on a very nice viewpoint. The Mahoosuc trail on the other side of the road follows a drainage and can be wet at times. There is a spring called Popsy spring (signed) that is quite high up the trail. Soon after the trail heads into the softwoods and then pops out on the ledges. Great views