Inspiring Ride: Circling Gloucester by Bike

September 29, 2022 / Outdoor Adventures, Things to Do & See

Inspiring Ride: Circling Gloucester by Bike | Gloucester Writers Center

With summer in the rear-view, the ring road encircling Gloucester and Rockport offers big, inspiring views—and a bracing ocean breeze. 


Half of Gloucester lies on the mainland. The rest shares an island with Rockport—which was, incidentally, part of Gloucester until 1840. Massachusetts Route 127 (and its brief offshoot, 127A) run around the island, mostly hugging the shore. These routes carry names including Washington, Langsford, and Granite Streets, depending on where you are at any moment. In autumn, beach crowds now a memory, we love taking to these scenic highways and byways on two wheels, seeking salt air and fodder for good stories.


The middle of the island is mostly wild. Civilization huddles along these streets and the roads and neighborhoods that stem from them. Which means, of course, plenty of places to hop off and explore, fuel up—and even take a dip in the ocean! (Remember, the air is usually colder than the water this time of year.) And because these routes circumnavigate the whole island, you can begin and end where you like. Save a full day to complete the loop in one go, with stops; or take it piece by piece, neighborhood by neighborhood, at your leisure.


Wherever you set out, be sure to consult a map. On a recent, cool morning we began from Downtown Gloucester, following Maplewood Avenue north. Our route took us down Cherry Street, past the entrance to Dogtown (another day!), and then to 127 via Stanwood Avenue. We chuckled, of course, at Clam Alley, across the way, before hanging right onto Washington Street and beginning the loop in earnest. We took notebooks and cameras along, filling them with images to inspire stories and writing for days to come. Below, some highlights from our trip to help inspire your own.


A word of advice: A full circle of the island includes numerous small to medium hills, as well as quirky turns on (usually) narrow roads. No grade was unmanageable for a couple poets who are average bikers, but the grade changes occasionally kicked our butts! Wear a helmet, and watch out for cars (a mirror helps). And above all—take your time. Savor the view and the feel of the cold, autumn road under your tires. 



This tiny residential village sits where the Annisquam River meets Ipswich Bay. Settled by colonists in the 17th century, it’s one of the oldest parts of Gloucester as we know it today. From Washington Street, heading north, turn left onto Leonard Street at the Annisquam Village Church to find quaint, old architecture fabulously preserved. 


Photo of Folly Cove by Kendra Dott


Leaving Annisquam, we headed through the Lanesville neighborhood. Stay on Washington Street to briefly leave 127 and detour inland; consult a map here to find public access to some of the abandoned quarries that dot the island’s interior. As you near the very top of the island, back on Washington Street, slow down to take in Folly Cove on the left, and be careful as you turn—the view is a breathtaking distraction of the highest order. On a windy day, white caps dance furiously in the distance. 



Head into downtown Rockport, where we refueled with sandwiches at Whale’s Jaw Cafe. (Note to self: come back for a concert here!) After, we pedaled to T Wharf for a postcard view of Motif #1. When you pick up again, we recommend taking 127A back toward Gloucester as we did. This short alternate hugs the coast and affords a wonderful, big sky, beach-after-beach panorama. 



Deviate from the numbered route once more to catch even more autumn coastline. At Bass Street, turn left to leave 127A and follow onto Nautilus Road, and then Atlantic Road, for astonishing, unobstructed views of rock and water. We traced Atlantic Road to Farrington Avenue, then followed Eastern Point Road to the entrance of Rocky Neck. A working artists’ colony to this day, the tiny peninsula juts into Gloucester’s inner harbor. Follow Rocky Neck Ave. to Horton Street, and then Horton to its end to find Ocean Alliance, a cutting-edge research center in an historic and picturesque paint “manufactory.”



Leaving East Gloucester, we passed through downtown to hook up once again with Rt. 127, this time to travel along the Boulevard (Western Avenue). One last glimpse of ocean—now looking toward Stage Fort Park and West Gloucester, over the Cut Bridge and off the island—from the Gloucester Fisherman’s Memorial to end our whirlwind ride.