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Sure, Cape Ann isn’t as sprawling or as renowned as Cape Cod. But that’s exactly what makes it a destination worth exploring. The four towns that make up the region—Essex, Gloucester, Manchester-by-the-Sea, and Rockport—offer up a bounty of natural beauty, art, history, and food, all with less driving and fewer tourist crowds than you’d encounter visiting its southern sister. 

“Cape Ann is incredibly beautiful and diverse,” says Ken Riehl, chief executive of the Cape Ann Chamber of Commerce. “What is so different about Cape Ann is the variety of what the communities have to offer.”

As you head up route 128, the first Cape Ann community you’ll encounter will be the tiny, gracious town of Manchester-by-the-Sea, a perfect place to enjoy postcard-perfect scenes of New England waterfront life. The town is mainly populated by commuters who choose to nest there for the beautiful homes, highly rated schools, and traditional charm.

Masconomo Park. Photograph by Tony Scarpetta

Visitors, however, enjoy the compact, walkable character of the town. Grab a coffee and a snack at Allie’s Beach Street Café or the Laughing Gull and stroll over to Masconomo Park to watch boats cruising in and out of the harbor, or continue a half-mile up the street to the famed Singing Beach. 

If you feel like shopping, browse Cuddlefish boutique for gifts for mother and child, explore the towering piles of used books at Manchester by the Book, or hunt for a great bargain at The Stock Exchange, an exceptionally well curated consignment shop with whimsical window displays.

If you’re after more natural beauty, follow route 127 towards Gloucester and visit Coolidge Reservation, a pleasant wooded trail that leads to a sweeping oceanside lawn, or get even further off the beaten path by popping into the downtown hardware store for a trail map of the Manchester-Essex conservation areas.

Up the road from Manchester-by-the-Sea is Essex, a town rightfully best known for its profusion of antique shops: More than 20 are in operation along one short stretch of route 133, offering everything from curated collections of high-end furniture to piles of knick-knacks you’ll have to dig through to find that perfect, unique treasure. 

But don’t be so distracted by the vintage values that you forget to take in the stunning view of the Essex River winding through the Great Marsh. Consider grabbing a drink or a meal—weather permitting—on the patio at Great Marsh Brewing Co. or local favorite CK Pearl to relax at a comfortable social distance while you enjoy the scenery. 

The biggest town—actually a city—on Cape Ann is Gloucester, the iconic fishing town that has both a long artistic heritage and deep working-class roots. The downtown is packed with independent shops selling new and used books, cheese and wine, handmade pasta, the work of local artisans, and almost anything else you can imagine. 

Singing Beach. Photograph by Tony Scarpetta

“The vast majority of the businesses here are mom-and-pops,” says Kory Curcuru, founder of the The Bridge Cape Ann, a community social media company based in Gloucester. “There aren’t a lot of big boxes and franchises here.”

As you stroll the downtown, keep your eyes open for the art that is such a part of Gloucester’s character. There are galleries aplenty, murals adorning narrow alleys, and sculptures near the Cape Ann Museum—visit the sea serpent that guards the museum door for a touch of maritime magic.

When it’s time for dinner, the seafood options are plentiful, from the ocean views from 1606 at the Beauport Hotel to high-end Italian fare at Tonno to takeout fish and chips from Turner’s Seafood Market. There are also options for Thai noodles, spicy tacos, fried chicken sandwiches, and wood-fired pizza. Many spots offer outdoor seating, and some are also open for indoor dining, but many are still operating on a takeout-only model, so be sure to check ahead.

Visitors should also take time to discover the natural side of Gloucester. Drive along route 127 for charming views of the Annisquam River and Lobster Cove, or head into the woods in historic Dogtown, hilly Ravenswood Park, or sprawling Tompson Street Reservation. 

At the very tip of the peninsula sits Rockport, a small, tight-knit community most often thought of as the home of the quaint red fishing shack known as Motif #1 and the quaint row of waterfront shops along Bearskin Neck. And while those sights are worth a visit, there is so much more to the town says Sarah Kelly, founder of Rockport Exchange, a nonprofit that promotes cultural events and activities in the city.

Photographs by Hannah Daigle

Less than a mile outside town, Seaview Farm raises grass-fed beef (we highly recommend grabbing some burgers to take home and grill) and sells produce from area farms, craft beer and wine, and other treats produced by local makers. Wander just a bit north of the downtown core and discover a pretty pair of beaches that keep the calm of the sea close at hand. “The fact that you can be right in town and yet have ocean access is really, really cool,” Kelly says. 

Rockport has, in recent years, become known for its festivals, from the autumnal food-and-music celebration of Harvestfest to the holiday season Rockport Makers Festival. These gatherings were all put on hold or went virtual last year, but the impulse behind them remains, Kelly says. 

“It highlights our communal spirit,” she says. “We really come together as a community and want to celebrate where we live and want to share it.” 

Must-Do: Eat + Drink

Turners Seafood Gloucester Market
Pick up some fresh, local fish or housemade stuffed clams to take home, or order up some fish and chips to go and head to a waterfront bench for a perfectly Gloucester al fresco meal. 4 Smith St., Gloucester, 978-281-7172,

Virgilio’s Italian Bakery
Try a taste of Gloucester’s Italian heritage with a stop at this local institution for a sandwich piled with freshly sliced cold cuts, a few cream-stuffed cannolis, or a loaf of semolina bread made on-site. Imported pastas, sauces, and other Italian specialties are also available. 29 Main St., Gloucester, 978-283-5295,

Short & Main
Founded by chefs trained by locavore icon Alice Waters, this casually sophisticated eatery offers wood-fired pizzas and fresh pastas crafted with impeccable—and delicious—attention to detail. 36 Main St., Gloucester, 978-281-0044,

An elegantly cozy atmosphere, the freshest local seafood and produce, and an extensive wine list help make this Italian eatery a favorite of visitors and devoted locals alike. 2 Main St., Gloucester, 978-879-4795,

C.K. Pearl
Beautifully prepared dishes with a beautiful view of the marsh. 112 Main St., Essex, 978-890-7378,

Great Marsh Brewing Company 
A newcomer to the food and beverage scene in Essex, Great Marsh offers great beers for takeout and an extensive to-go dinner menu. 99 Main St., Essex, 978-890-7827, 

DownRiver Ice Cream
It’s worth the drive to the outer edge of Essex to indulge in some of the best ice cream Cape Ann has to offer. Choices range from the simple, like the rich, custardy vanilla, to over-the-top flavors like the candy-studded Willy Wonka Explosion. 241 John Wise Ave., Essex, 978-768-0102

The Mill
The Mill opened mid-pandemic, and locals quickly flocked to its selection of coffee, freshly made sandwiches, and delicious homemade prepared comfort foods, all served up in a warm and friendly atmosphere. 121 Eastern Ave., Essex, 978-890-7139,

Allie’s Beach Street Café
Try a decadent breakfast sandwich, housemade soup served up in a crusty bread bowl for lunch, baked camembert with balsamic glaze for an afternoon snack, or braised shortribs for dinner. The husband-and-wife duo behind this eatery do it all—and do it all very well. 35 Beach St., Manchester, 978-704-9571,

Brothers Brew/Brackett’s Oceanview Restaurant
In the front, the small coffee shop serves up caffeine, sandwiches, and pastries—do not leave without sampling a donut or four. In the back, the seasonal restaurant offers seafood, steak, and amazing views. 27 Main St., Rockport, 978-546-3775/ 978-546-2797,

Feather and Wedge
The seasonal menu centers on local seafood and produce as much as possible, creating simple dishes packed with flavor. 5 Main St., Rockport, 978-999-5917,

This fried seafood joint is a North Shore icon for a good reason. You might have to wait in line, but the crisp fried clams and velvety chowder will make it worth your while. 119 Main St., Essex, 978-768-6451,

Must-Do: Shop + Renew

Beauport Hotel
A bar and restaurant with outdoor seating and gorgeous ocean views, a newly opened spa, and 94 luxurious rooms all make the Beauport an ideal destination for lunch and drinks or a weekend escape. 55 Commercial St., 978-282-0008,

Antiquing in Essex
With more than 20 antique shops along one mile of road, Essex is the ideal destination for all things vintage. Try Andrew Spindler Antiques to browse a curated collection of upscale pieces or Howard’s Flying Dragon to unearth a hidden treasure. Route 133, Essex 

The Paper Mermaid
Owner Mary Faino’s background as an artist is evident in this whimsical shop stocked with unique stationery (some featuring Faino’s own designs), imaginative art kits, and colorful, creative gifts. 57 Main St., Rockport, 978-546-3553,

Rockport Candle Co. 
Choose from handcrafted soy candles featuring dozens of different ocean-inspired fragrances or book a DIY session and customize your own perfect evocative scent. 5 Bearskin Neck, Rockport, 978-675-6001,

A charming boutique stocked with the cutest baby apparel, the most useful gear, and a few indulgences for Mom as well, from jewelry to skincare products. 26 Central St., Manchester, 978-704-9120,