Featured image: Samantha Labrecque Semle
You’ve heard of Cape Cod. Meet the other Cape! Cape Ann, Massachusetts, is a captivating corner of the North Shore where rugged coastline and historic harbors come together. From the working waterfront and maritime heritage of Gloucester to the charming streets, galleries, and seaside beauty of Rockport, this coastal destination offers endless ways to explore. Whether you’re looking for local flavors to savor, a welcoming place to stay, or adventures along the shore, this guide highlights the best of Cape Ann’s unique communities.
Eat
1606 Restaurant & Oyster Bar; Gloucester
Located inside the Beauport Hotel, the restaurant serves New England flavors with fresh local ingredients, a modern American menu, and a standout raw bar featuring oysters and other seafood favorites. Whether you’re enjoying a leisurely brunch, a sunset dinner on the oceanfront deck, or a cocktail by the water, 1606 is the perfect spot to take in sweeping ocean views in a relaxed atmosphere.
Short & Main; Gloucester
Located in the heart of Gloucester, Short & Main is a beloved neighborhood restaurant known for its wood-fired pizzas, fresh oysters, and seafood dishes. With a relaxed setting and a menu that changes with the seasons, Short & Main is a perfect stop for a casual lunch or dinner in downtown Gloucester.
A coastal-inspired mobile espresso cart serving Gloucester and the surrounding Cape Ann area, By the Sea Coffee brings handcrafted coffee to wherever the community gathers. From espresso drinks to seasonal specialties, you can find them often by the boulevard in Gloucester.
Located in the heart of Rockport, The Ice Cream Store is a classic Cape Ann stop for handmade ice cream, sweet treats, and seaside indulgence. With a wide selection of flavors and a welcoming, old-fashioned atmosphere, it’s the perfect place to enjoy a cone while exploring Rockport’s charming streets and waterfront.
Roy Moore Lobster Co.; Rockport
A Rockport institution since 1918, Roy Moore Lobster Co. is a must-visit for fresh, locally-sourced seafood and classic New England lobster fare. Located along Bearskin Neck, this casual waterfront spot serves up lobster, clams, oysters, and other seafood favorites in a no-frills setting that captures the true character of Cape Ann’s fishing heritage.
All Dough is a neighborhood bakery and café known for freshly made breads, pastries, and delicious coffee. It’s a welcoming stop for a morning coffee, a sweet treat, or something delicious to enjoy while exploring Cape Ann.
Located at the Bearskin Neck Motor Lodge, The Hideaway offers a relaxed dining experience in one of Cape Ann’s most charming coastal settings. Take in epic ocean views just feet from the water and enjoy bites alongside crafted cocktails.
A beloved Rockport seafood destination, The Lobster Pool offers classic New England fare with breathtaking views of the Atlantic. Known for fresh lobster, chowder, and other local favorites, this casual waterfront spot captures the laid-back charm of Cape Ann dining. With picnic tables overlooking the water, it’s the perfect, no-frills place to enjoy a meal by the sea.
Minglewood Harborside; Gloucester
Located on Gloucester’s working harbor, Minglewood is a lively restaurant offering American cuisine, craft drinks, and a fun atmosphere. With views of the waterfront and a menu designed for casual dining, it’s a lively gathering place to experience the energy and character of Cape Ann’s harbor scene.
Blue Collar Lobster Co; Gloucester
Blue Collar Lobster Co. celebrates the city’s working waterfront with fresh, locally sourced seafood and classic New England flavors. Known for its casual atmosphere and high-quality lobster, seafood rolls, and seasonal favorites, it’s a great spot to enjoy an authentic taste of Cape Ann’s maritime heritage.
Oak to Ember brings a modern approach to coastal dining with wood-fired cooking and a focus on seasonal ingredients. Known for its thoughtfully crafted dishes, warm atmosphere, and creative menu, this restaurant blends Cape Ann’s coastal character with delicious contemporary flavors.
The Salted Cod Arthouse; Gloucester
This hidden gem in Gloucester’s Rocky Neck community is housed inside an old 1880s warehouse and fish processing plant. It was originally used for smoking and salting fish before becoming a warehouse for copper bottom paint in 1892, when it was owned by the Tarr & Wonson Paint Company—the first U.S. manufacturer of copper paint. At high tide, sailors could pull right up to the back door (which is still intact today!) to load paint directly onto their vessels. In 1948, the space was transformed into an art gallery, and today it’s a cozy, weathered watering hole serving wine, local art, and light provisions to sailors, fishermen, artists, and curious passerby exploring America’s oldest fishing port and one of the country’s oldest working art colonies.
Seaport Grille offers an elevated dining experience with stunning harbor views and a refined coastal atmosphere. When dining here you can expect fresh seafood and craft cocktails that blend Cape Ann’s maritime character with upscale waterfront dining.
51 Rocky Neck is a neighborhood restaurant and bar that reflects the creative spirit and maritime character of the area. With a menu featuring thoughtfully prepared dishes, craft cocktails, and a relaxed yet polished setting, it’s a great place to settle in after exploring the galleries, studios, and waterfront charm of one of America’s oldest art colonies.
Castaways Café blends an island-style coffee shop with a charming boutique. Start your beach day with one of their popular smoothies, açaà bowls, or a handcrafted coffee, then browse their curated collection of coastal-inspired goods. With its relaxed, creative vibe, Castaways is the kind of place you’ll want to linger a little longer.
A Gloucester favorite with a true neighborhood feel, Charlie’s Place is the kind of casual spot where good food and friendly service take center stage. Known for its generous portions, comfort-food classics, and welcoming atmosphere, it’s a hidden local gem for seafood lovers and landlubbers alike.
Located at Gloucester’s Harbor Loop, Decklyn’s offers a coastal dining experience in a lively atmosphere. It’s a great spot to settle in for a waterfront meal with friends or family with the just the right amount of a modern neighborhood feel.
Stay
The Highliner Hotel; Gloucester
The Highliner Hotel is an 11-room luxury boutique hotel set inside a historic 1865 building in the heart of downtown Gloucester—America’s oldest seaport. The charming New England hotel captures the spirit of Gloucester; the design is equal parts moody and nautical, where deep coastal tones marry the stately grit of 1865 brickwork with a luxe design and rich maritime heritage for the modern day voyager. It is conveniently located just steps from the working waterfront, art galleries, shops, and restaurants in town. Plus, the hotel is a comfortable yet sophisticated home base to return to after a day of exploring Cape Ann.
Play
Shop Main Street; Gloucester
This part of downtown is filled with locally-owned shops, galleries, and small businesses that showcase the creative spirit of Cape Ann. From unique gifts and coastal-inspired finds to art, antiques, and specialty goods, it’s the perfect place to browse and wander. Some notable stores include: Main Street Arts & Antiques, The Brass Monkey, The Bookstore of Gloucester, Denim on Denim, and more!
One of Gloucester’s most beloved beaches, Good Harbor Beach is known for its soft white sand, rolling dunes, and stunning ocean views. A favorite spot for swimming, sunbathing, and long walks along the shore, the beach offers classic New England coastal scenery with plenty of room to relax. Visit at low tide to walk across the sandbar to Salt Island, or stay for sunset when the shoreline becomes one of Cape Ann’s most beautiful views. The beach fills up very quickly in the summertime, so the city uses Blinkay, a beach parking reservation system, for non-resident beachgoers. Reservations can be made up 10 days in advance on the mobile app or website. Reservations are required for non-resident parking at Good Harbor Beach.
Stroll Bearskin Neck; Rockport
A visit to Rockport isn’t complete without a walk along Bearskin Neck, one of Cape Ann’s most iconic destinations. This charming waterfront stretch is lined with colorful shops, art galleries, restaurants, and working harbor views that capture the town’s creative folks and maritime spirit. Take your time wandering the narrow lanes, browse local artwork and coastal finds, and enjoy the scenery that has inspired artists for generations.
See Motif No. 1; Rockport
Standing at the end of Rockport’s harbor, Motif No. 1 is one of America’s most recognizable and frequently painted landmarks. This iconic red fishing shack has inspired generations of artists with its simple design, weathered character, and picturesque waterfront setting. A symbol of Rockport’s rich artistic heritage, it’s a must-see stop for a photo and a chance to experience the view that has captivated painters for more than a century.
Halibut Point State Park; Rockport
Located on the rocky coastline of Rockport, Halibut Point State Park offers some of the most dramatic ocean views on Cape Ann. Once the site of a working granite quarry, the park combines natural beauty with a glimpse into the area’s industrial past. Wander the scenic trails, explore the historic quarry, and take in sweeping views of the Atlantic that stretch toward Maine on a clear day. Parking costs $5 for Massachusetts residents and $20 for non-residents (per car).
Join Cape Ann Harbor Tours for a hands-on lobstering demonstration aboard the King Eider. If you have ever wondered how lobsters were harvested, this is your opportunity to see the action. On this tour you’ll learn all about lobsters and lobstering, help with the haul, and enjoy a narrated tour of historic Gloucester Harbor, captained by a prior commercial fish- and lobsterman.
Gloucester Fisherman’s Memorial; Gloucester
Overlooking Gloucester Harbor, the Fisherman’s Memorial is a powerful tribute to the men and women whose lives have been shaped by the sea. The iconic bronze statue of a fisherman at the wheel honors the thousands of Gloucester fishermen lost at sea. A meaningful stop along the waterfront, it offers a moment to reflect on Gloucester’s fishing history and the generations who have built their lives around the ocean.
