Riding the ‘Other’ Cape: Cape Ann

Kettle Cove Mass
Mid-morning sun warms Kettle Cove at low tide. Photos by the author.

When New Englanders talk of “The Cape,” typically they mean Cape Cod, the flexing arm of Massachusetts that reaches from the South Shore into the Atlantic. But there’s another peninsula jutting into the Atlantic off the North Shore: Cape Ann. Here you’ll find “America’s Oldest Seaport,” scenic beaches, fresh seafood, stunning vistas and narrow, winding roads connecting it all.

Cape Ann motorcycle ride
A map of the route taken, by Bill Tipton/compartmaps.com.

The ride begins on State Route 127 in Beverly. You pass the oceanfront campus of Endicott College, where my daughter and money are both going. Each July, Endicott’s ocean-front Misselwood Cottage hosts a Concours d’Elegance, an event that may help you source a vintage Rolls-Royce or Duesenberg for the carriage house at your seaside estate.

Cape Ann motorcycle ride
Homes built on rocks are common on Cape Ann’s coastline. As my wife likes to say, “That would do.”

As Route 127 winds through Prides Crossing, the region’s rocky geography becomes apparent. Homes are often made with stone, surrounded by stonewalls or built on rock outcroppings. The Singing Beach in Manchester-by-the-Sea presents a fun phenomenon: dry sand that creaks as you walk on it.

Cape Ann motorcycle ride
In Manchester-by-the-Sea, the lobster boat Diana Lee rests on stands in a yard. After a long Cape Ann winter, it should be back on the water soon.

In Kettle Cove Village, turn right onto Ocean Street to hug the shoreline along White Beach and then Black Beach before rejoining 127. In Magnolia, a right off 127 onto Shore Road takes you past some of Cape Ann’s grandest homes and stunning ocean vistas. The views certainly beat the road. I encountered one section with potholes that could swallow a Buick. “I like the bumps,” a cheerful old woman in front of her home told me. “It keeps people from passing through.” Guess I missed that memo, ma’am.

Cape Ann motorcycle ride
The elderly woman whose house commands this view came outside. I said, “Sure is beautiful here.” She replied, “The only way I’ll ever leave is in a pine box.”

Beyond those bumps I returned to 127 and found Hammond Castle, where a museum displays inventions of John Hays Hammond, Jr. (1888-1965). Hammond held more than 400 patents, many related to radio remote control. You might thank him next time you change channels from the couch.

Gloucester (natives say “GLOSS-tuh”) calls itself “America’s Oldest Seaport.” Settled by English immigrants in 1623, Gloucester rises above a natural harbor. For nearly four centuries, fishing has been the community’s lifeblood. It’s so engrained in local culture, Gloucester’s high school sports teams are called the Fishermen. An easy self-guided walk (less than 2 miles) takes you through Gloucester’s working waterfront and historic downtown. There’s way more than you can glimpse–or eat–riding by.

Stalwartly facing Western Harbor are two memorials to remind passersby that fishing at sea is a dangerous occupation. East of the drawbridge over Blynman Canal, the Gloucester Fisherman’s Memorial honors 5,368 Gloucester fishermen who have perished at sea since 1623 (officials now peg the total number lost at more than 10,000). The memorial includes “The Man At The Wheel,” a statue commissioned for Gloucester’s 300th anniversary in 1923. The inscription, THEY THAT GO DOWN TO THE SEA IN SHIPS, is borrowed from Psalm 107:23. West of the drawbridge is the Fishermen’s Wives Memorial, erected in 2001 to honor the faith, diligence and fortitude of the wives and families of fishermen.

Cape Ann motorcycle ride
On Gloucester’s waterfront, the Fisherman’s Memorial honors THEY THAT GO DOWN TO THE SEA IN SHIPS.

Beyond the Cape Ann Whale Watch terminal, turn right onto Route 127A for views of the harbor and also Boston on a clear day, especially from Niles Beach. At Good Harbor Beach there’s a large, flat parking area, a rarity in these parts. During the off-season (October through April), dogs are welcome here on even-numbered days. Today is April 16 and temperatures have spiked into the 80s. Good Harbor Beach is dog utopia and I make several new friends.

Cape Ann motorcycle ride
A warm, even-numbered, off-season day spells “dog central” at Good Harbor Beach.
Cape Ann motorcycle ride
Boo-Boo, a Bernese Mountain Dog/Golden Retriever hybrid, knows the best time to roll in the sand is when you’re wet.

Next up the coast is aptly named Rockport, for years a major source of granite for the eastern United States. Also historically an artists’ colony, Rockport has a different vibe than Gloucester. The historic business lane down Bearskin Neck, with its galleries, shops and restaurants, reminded me of Harry Potter’s Diagon Alley. Walk onto the breakwater for views of Rockport Harbor. After 127A merges back into 127, drop down to Granite Pier for views of Rockport’s Back Harbor.

If you haven’t needed lunch until now, just past Halibut Point State Park you’ll find the Lobster Pool. This old school, side-of-the-road, on-the-water eatery served me a sumptuous sandwich of yellowfin tuna–seasoned, seared and served rare, as nature intended (drool, drool). The view out back made it taste even better. Manhandling my bike into the one meager parking space that was available proved worth the effort.

Cape Ann motorcycle ride
The Lobster Pool’s yellowfin is seasoned, seared and served rare, as nature intended.

When 127 ends at the rotary, hop onto Route 128, cross the Annisquam River, and take the second exit to enjoy Concord Street, which cuts and curves through Cape Ann’s interior. The landscape is worlds away from the seacoast route thus far. When Concord Street merges with Route 133, continue into Essex, where more fresh seafood restaurants await. You’ll also find the Essex Shipbuilding Museum and the Essex Riverwalk, both worth a visit.

If you still haven’t eaten–or if you’re ready for more–stop at the Clam Box, an Ipswich institution for more than 80 years. Its tall, angled walls resemble a box of fried clams…hard to miss. Regulars suggest the fried whole-belly clams. A short ways farther, the route concludes at Winthrop Elementary School. Why here? I like the giant dog statue out front.

Cape Ann motorcycle ride
College Hall, an English Tudor-style mansion, highlights Cape Ann’s ubiquitous stone. Built in 1916 as a summer residence, today it houses the office of the president of Endicott College.

While this ride is just 54 miles, with frequent stops it can take all day. If you ride more and stop less, turn around at the end and reverse course for a different perspective. My advice is to ride here during the off-season. A warm day in April, May, September or October will have less traffic and fewer pedestrians that often clog these narrow oceanside streets in summer.

Enjoy riding the “other” Cape.


  1. No wonder I love Cape Ann so much! It certainly was a great place to grow up and romp through the woods and Stage Fort Park and the beaches were the greatest! Fun for every day❤️😊👍🏻👍🏻

  2. In Ipswich, it’s worth the ride down Jeffery’s Neck Rd. out to Great Neck and Little Neck. Beautiful scenery. Skip the Clam Box as The Choate Bridge Pub provides far better food without the wait. For an extended ride, head up Rt 1A and ride down Plum Island. Then head north again to Newburyport; always lots going on there.

  3. If I know Cape Ann , I do I just Finish my 104 Ride in Cape Ann North Shore Boston , my ride it like Just the Cream it 40 Miles round trip to my house in beverly I don’t ride anymore like in the pass so I have a Triumph bonneville t100 2018 I love this bike so I have 4,150 Miles only in Cape Ann it a Zen Ride .


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