Here are some of our favorite places to explore by bike, and routes to ride to them safely, from the Gloucester MBTA Train Station with the best views and least traffic:

Ride 1

St. Peter’s Square Waterfront and downtown shops and restaurants

Lock your bike at St. Peter’s Square and explore Main Street, Middle Street, and Rogers Street by foot

Ride 2

Good Harbor Beach

Enjoy the beach , crossing over the footbridge after locking your bike

Ride 3

Stage Fort Park and the Fisherman’s Memorial Statue



Ride along harborside Stacy Boulevard, see the Gloucester Fisherman’s Memorial and Statue, over the “Cut Bridge” and onward to Stage Fort Park on the harbor

Ride 4

Rocky Neck


The artist colony of Rocky Neck offers several galleries to explore, and this ride brings you to the historic Paint Manufactory with views of Gloucester Harbor and Ten Pound Island. Continue on to Eastern Point Lighthouse

Ride 5

Eastern Point Lighthouse (and Niles Beach)



Niles is a great beach to explore year round to relax, and to swim in the summer. Eastern Point Lighthouse marks the start of the 2,250’ long granite jetty, known as the  Dog Bar Breakwater, which you may explore by foot. Ignore the “private resident only” signs … these signs do not apply to bicyclists.

Ride 6

Bearskin Neck and Motif #1,  Rockport (along quieter, shoreline roads)



This ride brings you to downtown Rockport where you can explore waterfront wharves, Motif #1, art galleries, restaurants, and shops.

You can visit nearby Front Beach, for view, some sun and a swim