Cape Ann Road Trip

Photos by Fawn Deviney

Tour Cape Ann this summer and discover all this local coastal region has to offer. 

If we’re going to talk about visiting Cape Ann, we first need to define it. Adhering to the proper geographical definition, the region includes four picturesque seaside communities: Essex, Manchester-by-the-Sea, Gloucester, and Rockport. Once you start talking to locals, however, there is less agreement; according to some purists, Cape Ann comprises Rockport and Gloucester and nothing more.

However you define it, Cape Ann is one of Massachusetts’s most charming destinations, combining postcard-perfect ocean views, deep history, a thriving arts scene, and plenty of tempting spots to eat. Though you could easily spend an entire vacation exploring the region’s hidden nooks and roads less traveled, a leisurely day trip offers ample opportunity to sample the beauty of Cape Ann.

Any visit to the area starts on Route 128 North. Drive past the malls, chain stores, and office buildings until the highway is flanked by nothing but forest. Then keep going.

Hop off at Exit 16 to explore Essex or Manchester-by-the-Sea or continue a bit further and kick off your visit with a scenic loop through Gloucester and Rockport. When the trees fall away and the road rises to cross a steel span—known locally as merely “the bridge”—you have arrived. The water beneath and beside you is the Annisquam River, a narrow estuary that divides Rockport and much of Gloucester from the mainland.

At the end of the bridge, circle the rotary and turn onto Route 127. Before you go too far, consider a stop at Willow Rest, an eclectic shop and eatery that offers breakfast and lunch (the Dogtown sandwich with chicken, goat cheese, and arugula is a sure bet), coffee, baked goods, local eggs and cheeses, and handcrafted gifts made by area artisans.


As you continue along Route 127, you will soon catch sight of Lobster Cove, a narrow strip of water that sets off Annisquam, a tucked-away village mostly occupied by summer residents. The neighborhood is a tangle of narrow streets that can confound even natives, but if you happen through during breakfast or dinner hours—and it is worth trying to do so—you can, and should, enjoy a meal at The Market, a rustic, waterfront farm-to-table restaurant run by two alums of Alice Waters’s famed Chez Panisse.

Halibut Point and Folley Cove are great places to stretch your legs

Once you return to Route 127, the next few miles offer a rapid succession of scenic views as you pass through the tiny village of Lanesville and the ruggedly picturesque Folly Cove. Before looping south toward Rockport, swing into Halibut Point State Park. Two and a half miles of easy walking trails feature rocky headlands, tidal pools, a scenic overlook, and slightly dizzying views into a historic water-filled granite quarry.

A few miles farther down the road, Rockport offers a little more bustle. The iconic red fishing shack, Motif No. 1, is easily the town’s most famous sight, but dozens of shops, galleries, and cafés are also well worth your attention. The Rockport Art Association inhabits a pair of renovated buildings on Main Street; the organization displays pieces from its collection and sells works by local artists as well as a selection of books, cards, and small sculptures. It’s free to visit, but donations are appreciated.

Side Trip: Lanesville's July 4th renegade parade is the chance for locals to take the town by storm, pound on drums, and march into the ocean while singing the national anthem.


Wander along Bearskin Neck— named, legend has it, for a valiant Colonial Era battle between man and bear—to browse shops selling jewelry, T-shirts, and all manner of quirky clothes and household decorations. Just off the Neck, check out Lula’s Pantry for gourmet foods and intriguing kitchen wares, La Provence for French country-style table linens and décor, or Tuck’s Candies for handmade sweets.

Spin Around: If you have strapped your bike to the back of your bumper, unhitch it and set your wheels spinning to the 25-to-30 mile loop around Gloucester, Rockport, and Annisquam. Enjoy coastal vistas, state parks and a rest stop in Bearskin Neck.


From Rockport, follow Route 127A toward Gloucester, where the houses to your left eventually give way to grassy marshes and dark, snaking creeks stalked by graceful egrets and herons. At the corner of Bass Avenue, take a left to swing by the far end of Good Harbor Beach, and then continue along Atlantic Road to enjoy the dramatic rocky stretch of coast known to locals as the Back Shore.

Keep an eye out for the sign designating Tragabigzanda Road. The short residential side street is a rare reminder of one of the region’s first names: 17th-century adventurer John Smith originally dubbed the area Tragabigzanda in honor of a beautiful, young aristocratic woman he had known in Turkey.

Fishermen's Memorial

At the end of the Back Shore, the road turns sharply and drops down to Niles Beach and Eastern Point. Follow Eastern Point Boulevard, a waterfront strip lined with brick mansions and sprawling shingled summer homes, until the road ends at the Eastern Point Lighthouse—built in the 19th century to mark the entrance to Gloucester Harbor. A long granite breakwater and a half a mile of easy walking trails in the adjacent wildlife sanctuary make for a leisurely stroll.

Before you complete your loop around East Gloucester, Rocky Neck is well worth a visit. The working artists’ colony has attracted and inspired painters and writers—including Winslow Homer, Fitz Henry Lane, and Rudyard Kipling—for more than 150 years. The cluster of narrow streets gives way to sweeping harbor views, and is home to many vine-draped cottage studios and galleries.

From Rocky Neck, a few more minutes on the road will place you in downtown Gloucester under the watchful gaze of the Gorton’s fisherman. The main drag comprises a friendly mix of restaurants, coffee shops, vintage stores, boutiques, and gift shops. The Green Life natural living store offers a wide selection of eco-friendly home goods and clothing, while The Menage Gallery features handmade wood furniture and décor.

If you’re hungry, eateries abound in downtown Gloucester. For a super solid sandwich and a taste of the city’s Italian roots, Virgilio’s, a local institution, can’t be beat. Feeling more like a sit- down meal on a waterfront deck? Latitude 43 is always a good choice for creative seafood-heavy fare and fun modern sushi.

If you are new to Gloucester, swing down Stacy Boulevard to see the Gloucester Fishermen’s Memorial—often called The Man at the Wheel— the quintessential symbol of the city. Around the corner is Stage Fort Park. Historically the site of massive platforms for drying fish, the park is now a popular recreation spot featuring a small beach, playgrounds, picnic tables, and a spacious grassy area for picnics and play.

To reach the remaining two towns that constitute Cape Ann, hop back on Route 128, or meander down back roads if you haven’t had your fill of magnificent ocean scenery.

Picnic Spot- Willow Rest: Stop in at this fun little eatery/shop for goodies - its sandwiches and pizzas make for the ideal picnic fare.


Though tiny, downtown Manchester includes several gift shops and galleries worth visiting. For vintage finds, check out The Stock Exchange, where whimsical window displays highlight some of the store’s best merchandise, and Manchester By the Book, a used book store that virtually overflows with everything from antique volumes to pre-owned contemporary favorites.West of Gloucester lies Manchester-by-the-Sea, a small, but exceedingly charming town. Perhaps most popular is Singing Beach, named for the sound the sand is said to make under walking feet. Singing Beach is favored by visitors who take the MBTA commuter rail into town and make the pleasant walk—less than a mile—down to the water. If you spend any time at the beach, treat yourself to a stop at Captain Dusty’s, a seasonal ice cream shack that serves very generous dishes of its decadent homemade ice creams and sorbets.

Singing Beach

Hiking- Coolidge Reservation: On the eastern edge of town, Coolidge reservation is a 66-acre property where a short hike along the woodsy trail brings you to a rolling green lawn stretching down the rocky shoreline. For a slightly brisker walk, a mile-long hike to the top of Bungalow Hill yields panoramic views. Rarely crowded, the reservation can be a tranquil spot to stop for a break or a stand-alone destination for a few hours to escape. 


Neighboring Manchester, Essex is celebrated for its antiques stores—more than 20 along a one-mile stretch— but it also has other, less well- known attractions. Colonial-era farmhouse Cogswell’s Grant today houses an eclectic and fascinating collection of folk art; the grounds of the 165- acre property are also open to visitors. Just up the street, the Essex Shipbuilding Museum offers a glimpse into the history of the town’s bygone shipbuilding industry.

After you’ve finished that ice cream cone, gazed at the scenery, strolled the trails, browsed the shops, and absorbed the history, it may be a little disappointing to pull onto the highway and watch the real world blink back into existence. But don’t worry—you can always return.

Essex Antiques

What to eat: When you're ready to eat, Woodman's of Essex is the classic choice for fried seafood. J.T. Farnam's is also a good pick, with award-winning chowder, marginally shorter lines, and spectacular marsh views. Downriver Ice Cream is on the northern edge of town, but the drive is worth it for homemade flavors like snail trail- vanilla with chocolate chips and peanut butter- rasberry cheesecake. 


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