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.
Hop onto Route 128 North. Drive past the malls, chain stores, and office buildings until the highway is flanked by nothing but forest. Then keep going. Get off at exit 16 if you want to explore Essex or Manchester-by-the-Sea.
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 bookstore that virtually overflows with everything from antique volumes to pre-owned contemporary favorites.
From Manchester, travel north on scenic Route 127 for a winding road with gorgeous ocean views. You’ll soon hit Gloucester. If you’re hungry, eateries abound downtown. 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.
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.
On your way out of Gloucester, head down to the Back Shore for even more breathtaking views. 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.
Next up is Rockport. The iconic red fishing shack, Motif No. 1, is easily the town’s most famous sight, but dozens of shops, galleries, and cafes are also well worth your attention. Just off Bearskin Neck, check out Lula’s Pantry for gourmet foods and intriguing kitchen wares, La Provence for French country-style table linens and decor, or Tuck’s Candies for handmade sweets.
If you want to stretch your legs at this point, head north of Rockport to Halibut Point State Park. Take in the salty sea air and rocky cliff views while exploring all the trails and tidal pools of the area.
You won’t want to miss 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 brunch or dinner hours—and it is worth trying to do so—you can, and should, enjoy a meal at Talise, in the former space of The Market, featuring creative and inventive seafood dishes from chef Joshua Smith.
If it’s dinnertime by now, head to the famed Woodman’s of Essex, a family business that’s been serving up authentic fried seafood for over 100 years. Essex is also home to some of the best antiquing on the North Shore. Cap off the day at the iconic Crane Beach just up the road in Ipswich. Some of Greta Gerwig’s Little Women was even filmed there. Check to see if they’re hosting one of their socially distanced outdoor concerts on the day you go.