Cape Ann Cruise

Gloucester, Massachusetts 1930

Cape Ann Cruise

Cape Ann Cruise Professional Review and Guide

"This ride explores Boston's North Shore. The shorter 22-mile loop circles the rocky shores of Cape Ann, where fishermen's cottages and grand summer homes now share the ocean views. The route passes through the working waterfront of Gloucester and the harbor towns of East Gloucester, Rockport, and Annisquam, favorites of both artists and tourists. The longer loop includes more coastal towns as well as the Hammond Castle Museum, a medieval-style castle.

Terrain: flat to slightly rolling coastal route. Traffic/Safety: sections of rough road, especially on the return from Rockport to Annisquam and Gloucester. Weekend summer traffic may be especially heavy. Also, use caution in the commercial district of Gloucester and at the rotary at Grant Circle at 28.6 miles."

Cape Ann Cruise Reviews

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8/7/2008
View was great. I highly recommend stopping off in Gloucester for some Chowda and a beer and then continuing along.
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9/22/2007
One of the best rides near Boston. Good roads, great ocean views, the footbridge at Annisquam,etc.
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8/9/2005
Easy to follow (just keep the ocean on your right) with lots of interesting distractions (e.g., Good Harbor Beach)and beautiful views along the way.
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Trail Information

Gloucester
Nearby City
36.4
Distance
Loop/Lollipop
Trail Type
Moderate
Skill Level