Gloucester's many villages and neighborhoods, and the towns of Rockport, Manchester and Essex, were all settled back when boats were the best form of transportation.

Towns and village centers grew up around the edges of the best harbors, the places where boats could be tied up safe from storms.

So you have Annisquam on the deep Lobster Cove, Lanesville on the sheltered Lane's Cove, downtown Essex as far up the Essex River as boats could navigate. And on one of the best harbors on the East Coast - Gloucester Harbor - you have the most crowded neighborhood on Cape Ann.

For years there was nothing but a few scattered farmhouses between the small villages because there was no cove or harbor at all - such as in the long stretch between Rockport's Pigeon Cove and Lanesville.

And the roads that ran between those harbors and coves tended to be long, twisted and winding. Nobody much lived on them, after all, and nobody bothered to use them when a boat was faster and easier.

The entire center of the island - the portion of Gloucester and the town of Rockport on the ocean side of the Annisquam River - was never really built up. And as a result, you have to go eight miles to get from Annisquam on one side of the island to downtown Rockport on the other, even through they're only about two miles apart as the crow flies.

Besides stringing out the population, the way Cape Ann was settled had an effect on where the roads were built.

Cape Ann's roads tend to radiate outward from the best harbors, or run around them - something like the spokes and rim of a wheel, with the harbor being the axle. That makes for some weird intersections.

If you want to negotiate the odd intersections and the narrow roads in between, here's a quick guide to Cape Ann, starting from the downtown on Gloucester Harbor and extending clockwise around the island (See map on pages 40 and 41).

West of the harbor, Western Avenue (Route 127) runs across the Annisquam and heads first to Magnolia, once the preferred summer vacation spot for the wealthy of the Gilded Age. The road goes on to the town of Manchester.

On the same side of the river, but heading north, you go through West Gloucester and into Essex along Route 133.

If you stay east of the river and head north on Washington Street, you would pass through the villages of Riverdale, Annisquam, Bay View and Lanesville.

Known as the "Back of the Cape," these villages along the Annisquam River include some of the city's oldest homes, as they had some of the most sheltered harbors.

Past Lanesville on the northern end of Cape Ann, you encounter Folly Cove (never settled, as it was folly to leave a boat there in a northeast storm) and cross into Rockport.

Then there's another long stretch of road. It's known as Granite Street, alluding to the fact that this part of Rockport wasn't settled by people who came by boat, but by people who worked in the nearby granite quarries.

The next village is Pigeon Cove, and after a short distance you'll come to downtown Rockport.

Then it's another long jaunt along the coast before you get to East Gloucester. Most of Cape Ann's best beaches are along this stretch, but since beaches don't make good places for boats the land was uncrowded for many years.

East Gloucester is the peninsula that extends south of Bass Avenue and includes East Main Street and Rocky Neck. The ocean side of that peninsula is Bass Rocks or the Back Shore, while the tip is Eastern Point.

Cradled under the arm of East Gloucester is Gloucester Harbor, and you're back downtown.