The Mohawk Trail is as old as, well, I suppose "dirt" would be as apt a simile as any. Like many roads in New England, the trail got its start as a migratory game path originating somewhere west of the Taconic Mountains (in what's now New York state) and meandered eastward through what would eventually become Massachusetts. Native Americans, primarily the Mohawks in the west and the Pocumtucks in the Connecticut River Valley to the east, used the trail in their migrations and had long-established treaties regarding hunting and fishing rights along its length. Unfortunately, the arrival of the white man stirred trouble. Sensing that political unrest between the tribes would further their own ends, the English, located in Pocumtuck territory, and the Dutch, who were making inroads into Mohawk lands in the lower Hudson River Valley, began to manipulate one tribe against the other. Eventually a full-scale war broke out, with the Mohawks ultimately gaining the upper hand. Since no one ever names anything after the losers, the path eventually became known as the "Mohawk Trail."
With the end of the Indian Wars and the American Revolution, the old trail was gradually rerouted and widened to accommodate wagon traffic between the city of Boston and the interior towns, particularly North Adams. Ultimately the "Indian path" as it was then called became a road, although if you're so inclined, portions of the prehistoric track can still be hiked in the Mohawk Trail State Forest.
By the early part of the 20th century people began to appreciate just how beautiful the region encompassing the trail was, so in October of 1914 the Massachusetts State Legislature declared the Mohawk Trail a scenic tourist route.
The modern Mohawk Trail, officially Massachusetts Route 2, runs from Boston, Massachusetts, to Buffalo, New York, which makes it easily accessible from almost any direction. The real Mohawk trail, or at least the one that's most fun to ride, is the section between North Adams and Greenfield, Massachusetts. Obviously everyone is going to find his or her own way to the trail-since I live in western Connecticut, hard by the New York border, and prefer to ride the trail from west to east, what follows is my favorite loop.
If you're coming from the Greater NYC/New Jersey or Pennsylvania area, pick up 684 North and follow it until you hit the Route 22 intersection. About 6 miles up the road you'll come to the Putnam Diner, which is as good a place as any to stop for breakfast, lunch or dinner, and a convenient place to top off the tank. Take a right at the diner and follow Haviland Hollow Road to Route 37 in the town of New Fairfield, Connecticut, and from there take 37 to Route 39 North. Follow 39 to 55 East and about 2 miles later you'll pick up Route 7 North. These roads are all fairly interesting, and bend through wooded farmland and postcard-pretty New England towns. By picking up Route 7 in Gaylordsville, Connecticut, you'll also avoid the proliferation of urban commercial sprawl that's managed to tarnish its lower half.
The ride up 7 is always entertaining; it's a wide, smooth and reasonably twisty road with just enough roadside attractions and moderately priced eateries to make a quick leg-stretching stop worthwhile. The town of Kent, Connecticut, is particularly nice. There are several open-air cafs and an excellent ice cream parlor located on its main drag, as well as a first-rate bookstore (you can browse the outside sale tables on nice days), making it a pleasant spot to take a break.
Over the line in Great Barrington, Massachusetts, Route 7 turns into Main Street, U.S.A., with many sections moderately cluttered with everything from antique galleries to chain restaurants. Bear with it-the congestion doesn't last that long, and the town of Stockbridge, home of the real Alice's Restaurant, and the Pittsfield/Dalton area, site of the only U.S.-hosted International Six Day Trial (or enduro as it's now called), are worth visiting.
Farther up the road you'll come to the town of Adams, Massachusetts. When you do, start looking for the signs to Mount Greylock. The turnoff at Rockwell Road comes up quickly, but if you miss it you can turn around in the tourist information parking lot. At 3491 feet, Greylock is the highest peak in Massachusetts, and yep, you can ride right to the top-but bring a few singles, they charge to park. Camping is available, and the Bascom Lodge, a Civilian Conservation Corp project from the '30s now run by the Appalachian Mountain Club, can provide accommodations for up to 32 people. The lodge also has a small store selling supplies, books and souvenirs.
Coming down Greylock you'll follow the Notch road to Route 2, which is where the fun definitely begins. The real trail begins with the Hairpin turn, a climb up Hoosac Mountain. Halfway through the turn you'll find the Golden Eagle Restaurant. the food at the Eagle ain't fancy, but it's good and the prices are right. But even if you don't stop to eat, at least take a moment to check out the view from the parking lot. you'll be looking over several mountain ranges, four states and the breathtaking Hoosac Valley-to describe it as awesome doesn't do it justice.
On the downhill side of the mountain the trail winds along the Deerfield River, through the Berkshire foothills and across the Mohawk Trail State Forest. The scenery and the road are among the best I've ever found, although be forewarned that traffic, especially during the peak summer months and the fall leaf-peeping season (mid-October/early November), can be heavy, particularly on the weekends