You have been hiking in the Boston area for some time, and are comfortable with the more difficult local hikes in the Middlesex Fells and Blue Hills and are now ready to tackle easier hikes to 4,000 footers in the White Mountains of New Hampshire. Where do you start?
What follows are my suggestions for the first few 4,000 footer hikes. The distances are for a round trip. None is very long, but going uphill constantly is much harder than going up and down, as you do in the Blue Hills. The last two are probably unsuitable as the very first trip, but if you find the other trips easy you should be able to attempt them.
Mount Osceola by the Mt. Osceola Trail from Tripoli Road (6.4 miles; 2,050 feet). This is arguably the easiest of the Fours, with the least elevation gain spread over three miles, leading to uniformly easy grades. Add great views from the summit and a short drive from Boston and you can see why it is one of our most popular hikes. The only downside is that it is very rocky, even by White Mountain standards!
Mount Tecumseh. The Mt. Tecumseh Trail starts at the Waterville Valley ski area, goes over the summit, and descends to Tripoli Road. The overwhelming majority of hikers to it as a round trip from the ski area (5.0 miles; 2,200 feet). Since the trail is shorter than the Mt. Osceola Trail and gains more elevation it is obviously quite a bit steeper. I prefer to approach it from the Tripoli Road end (6.2 miles; 2,600 feet). There are a few views on the way up, and I find the forest on the north slope of the mountain, with its rich undercover of ferns, more attractive than the open woods of the usual trail. With two cars a traverse (5.6 miles; 2,400 feet) is a very enjoyable trip. It is also a short drive from Boston, unfortunately the views from the summit are limited.
Mount Hale by the Hale Brook Trail (4.4 miles; 2,300 feet). A short but steep climb through very pleasant woods. The summit itself is bare, but the trees that surround it are growing and the views are diminishing over time. Going down the Lend a Hand Trail to the Zealand Hut and then out by the Zealand Trail is an excellent trip, but it is too long to qualify as an "easy hike" (8.0 miles; 2,300 feet if you have two cars, add another couple of miles on the road with one car).
Mount Jackson by the Jackson Branch of the Webster-Jackson trail (5.2 miles, 2,150) is another short hike to a summit with excellent views. It has a few steep sections, and there is a short and rather easy scramble just below the summit.
Mount Pierce by the Crawford Path (6.4 miles; 2,400 feet) is one of the best easy 4,000 footers. The trail is nowhere steep, and the views from the exposed summit are excellent. You may want to make a loop going up (or down) by the Mizpah Cutoff to Mizpah Hut, then following the Webster Cliff Trail to the summit of Mount Pierce, which adds about 0.2 miles. Note that the section of the Webster Cliff Trail between the hut and the summit is steep with rough footing.
Mount Tom, by the Avalon, A-Z and Mt. Tom Spur trails (5.8 miles, 2,150 feet) is a nice hike to a summit that has acquired good views after a blowdown. The trail has reasonably good footing, and is never too steep. There are a couple of waterfalls (Beecher and Pearl Cascades) on a side path off the trail (signed). The summit itself has good views to the west, and shortly before reaching it there is a unmarked path that leads to views to the east (Crawford Notch and the Presidentials).
The next two mountains are more ambitious, and much more rewarding. They involve slightly greater distances and elevation gains, and their summits are above treeline, exposed to the weather. They are probably not suitable for a first trip to the White Mountains, but should be visited as soon as you feel comfortable. Bring warm clothes, even in summer! Not only are the views magnificent, but there is a feeling of spaciousness when you are well above the trees.
Mount Moosilauke by the Gorge Brook Trail (7.4 miles; 2,450 feet). The mountain is high, but so is the starting point, so the total elevation gain is reasonable. The grades are moderate and the footing good. There are some good views on the way up, but the real reward is after you emerge from the trees. The summit has views in all directions, and since it is the most westerly of the New Hampshire 4,000 footers these views include both the Green Mountains of Vermont and the Adirondacks of New York.
Mount Eisenhower by Edmands Path (6.6 miles; 2,750 feet) has the greatest elevation gain of any of the peaks described here. The trail is excellent, with good footing and easy grades, so it is not as difficult as the numbers might suggest. There are excellent views of Mount Washington, with the entire ridge from Mount Eisenhower, over Mounts Franklin and Monroe, to Mount Washington visible, all of it way above the trees. It is the hardest of these trips but, in my opinion, by far the most rewarding.