Once you have parked your car, proceed northeast on route 127A/ Main St., riding along the harbor. The street becomes Eastern Point Road, and you can already start exploring side streets, like Rocky Neck avenue on your right, where you will find quaint houses, painters shops and authentic small boat repair yards.

A great side trip is to turn left on Eastern Point Boulevard West, which opens behind a small stone gate on your right just before the road starts to climb. Do not be put of by the signs that prohibit entrance: there is a public right of way down to Eastern Point Lighthouse, a Coast Guard facility at the end of the road and a great place to have a full view of the Gloucester Harbor Bay. You can also get back there by walking—see our related destination, particularly adapted to families and kids.

Once back on the main road, now named Farrington St, then Atlantic Rd, you will explore Cape Ann by staying mostly along the shore. You generally follow the route 127A, which transforms into route 127 after Rockport. Rockport, about halfway through the ride, is a nice stop to have lunch. From there, if you start feeling tired or if the weather changes, you can shorten the ride by taking Main Street/Route 127 from downtown and go back in straight line to Gloucester (beware of heavy traffic on this road). Otherwise, continue along the coastline on Route 127 before riding back to Gloucester. Be extremely cautious when crossing the roundabout with Route 128. From there, route 127 becomes Washington Street. Turn left on Pine Street/Proctor Street, then right onto School St down to the Gloucester Harbor. Once there, you can make the extra effort to see the Fishermen Memorial (less than a mile away on your right on Western Ave/Route 127), or turn left and return to your car.

Once back in Gloucester, for those who loved the Perfect Storm, the Crow's Nest bar is facing the harbor, not far from Harborside Cycle, where you can rent bikes for the day.

Consider a full day for this ride, unless you are particularly fit and do not stop at the many vistas and points of interest along the way. There are few climbs, which most people can easily master at low speed. Start early if you rent your bike, as the bike shop closes at 5 pm on Saturday and 3 pm on Sunday.

There is more to see in the area than is described here, so you may want to bring a travel guide with you (if only to know where to find the best lobster in town).