Hi Umsaskis:
IMO, the best hike near Holyoke/Northampton is the M-M Trail/New England National Scenic Trail traverse of the Mt. Tom Range. You can spot a car near the Log Cabin at the south base of Mt. Tom, then cross Rt. 141 and take a herd path to the Telephone Line Trail, which is unmarked but easy to follow. I've done this hike several times and follow the telephone line to the Metacomet-Monadnock (M-M) trail crossing, after a steep, scrambly climb of maybe 300' vertical. The M-M is blazed white, and you take a left on it. It diverges into several herd paths. The funner ones, to my taste, are the ones which go furthest out on the cliffs, within reason. Keep ascending toward the radio and TV towers, which are at the summit, 1202', about 650 above your start and about 1050' above Easthampton. Follow the White Blazes north and rise and fall several times. If you follow the White Blazes to Mt. Nonotuck, the northern peak of the range, and then work your way back either by the road or side trails, it's about 9 miles. A nice day's hike with numerous great viewpoints, especially the 2 mile cliff walk, almost continuous, from Mt. Tom's summit to that of Whiting Peak.
IMO, this hike compares favorably with many in the Whites and higher Greens (the ones I've done so far). It's one I like to hit at least once a year and a great place for taking pics and taking in the views. There's a nice viewpoint about 0.3 north of Tom's summit, high up on rocky ledges, where you get a nice view between Deadtop (the next highest summit on the ridge to Tom) and Mt. Holyoke right across the Connecticut River. Between the two is UMass, and on a nice, clear day, right behind the ridge behind UMass is Mount Monadnock. Also, views to the West and North, between Mt. Tom and Whiting Peak (the third main peak of the range as you head north) pretty well continuously include Mt. Greylock and several VT peaks, including Mt. Haystack and Mt. Snow and, in places, Stratton. For so short a mountain, it has grand views - from Tom's summit and on the climb from the south, there are superb views along the Metacomet Ridgeline deep into Connecticut - downtown Hartford visible most days as well, Springfield certainly so.
Caution: keep in mind that copperheads do dwell in those hills - a guy was bitten by one, non-fatally so far as I know, last fall. There's a ton of foot traffic, though -it's probably the most popular hike in the Happy Valley - so the risk is probably minimized by that. Gaiters might be good attire. Also, there are some tricky, scrambly spots in places, both going up and down, but all passes are reasonably negotiable with proper care and attention.
PS: You can do one car if you like, or park in the state reservation. There are several options. Check out their website here:
http://www.mass.gov/dcr/parks/central/mtom.htm