Summer on Cape Ann | Things to Do, Restaurants & Where to Stay

The Ultimate Guide to Your Summer on Cape Ann: What to Do, Places to Eat & Where to Stay 

Cape Ann, Massachusetts, one of the best summer destinations on the North Shore, offers beautiful beaches, waterfront dining, scenic harbor views, and unforgettable coastal experiences. Located just north of Boston, the charming seaside communities of Gloucester, Rockport, Essex, and Manchester-by-the-Sea provide the perfect summer escape filled with outdoor adventures, fresh seafood, and classic New England charm. 

Whether you’re planning a Cape Ann day trip or a weekend getaway, this guide highlights the best things to do in Cape Ann during summer, including where to dine, where to enjoy sunset views, and where to stay for the ultimate coastal experience. 

Enjoy Rooftop Drinks & Live Music at Birdseye Rooftop in Gloucester, MA 

One of the best places to experience summer sunsets on Cape Ann is Birdseye Rooftop at Beauport Hotel Gloucester. Located overlooking Gloucester Harbor and Pavilion Beach, this rooftop destination offers panoramic coastal views, handcrafted cocktails, and live entertainment throughout the summer season. 

Guests can enjoy live music Sunday-Thursday with themed nights including Country Nights on Sundays, Reggae Nights on Wednesdays, and Sunset Sessions every Friday and Saturday featuring live DJ sets. 

Whether you’re searching for the best rooftop bar in Gloucester, MA, a place to watch the sunset on Cape Ann, or a unique summer night out on the North Shore, Birdseye Rooftop offers the perfect combination of ocean views, cocktails, and coastal atmosphere. 

Where to Eat on Cape Ann: Seasonal Dining at 1606 Restaurant & Oyster Bar 

Cape Ann is known for its incredible seafood and coastal dining experiences, and summer is the perfect time to enjoy the region’s fresh flavors. 

Located inside Beauport Hotel Gloucester, 1606 Restaurant & Oyster Bar offers elevated waterfront dining featuring seasonal New England cuisine, fresh oysters, seafood specialties, and handcrafted cocktails. 

The summer menu highlights locally inspired ingredients and seasonal favorites, making it an ideal destination for: 

  • Romantic dinners on Cape Ann  

  • Waterfront dining in Gloucester  

  • Celebrating special occasions  

  • Enjoying fresh New England seafood  

After a day exploring the coast, settle in for dinner with harbor views and experience one of Gloucester’s premier dining destinations. 

Experience Waterfront Dining & Summer Cocktails at Seaport Grille 

For a more relaxed waterfront dining experience, visit Seaport Grille in Gloucester. Located along the historic harbor, Seaport Grille combines fresh seafood, classic coastal favorites, and creative summer cocktails in a lively waterfront setting. 

Looking for the best waterfront restaurants in Gloucester, MA? Seaport Grille is a favorite spot to enjoy: 

  • Harbor views  

  • Outdoor summer dining  

  • Fresh seafood  

  • Seasonal cocktails  

  • Casual coastal atmosphere  

From afternoon drinks overlooking the water to dinner as the boats pass by, Seaport Grille captures the laid-back spirit of summer on Cape Ann. 

Best Things to Do on Cape Ann in Summer 

Beyond dining and rooftop evenings, Cape Ann offers some of the best summer activities on the Massachusetts coast. 

Spend a Beach Day at Pavilion Beach 

Located steps from Beauport Hotel Gloucester, Pavilion Beach is a beautiful spot to relax, swim, and enjoy classic New England coastal scenery. 

Go Whale Watching from Gloucester Harbor 

Gloucester is one of the best whale-watching destinations in Massachusetts. Set sail from Gloucester Harbor with Cape Ann Whale Watch for an unforgettable ocean adventure and the chance to see humpback whales, fin whales, and other marine life. 

Explore Rockport’s Bearskin Neck 

Just a short drive from Gloucester, Rockport’s iconic Bearskin Neck features local shops, art galleries, restaurants, and some of the most photographed coastal views in New England. 

Enjoy a Sunset Cruise or Harbor Adventure 

Experience Cape Ann from the water with a scenic harbor, sunset, or specialty cruise aboard Beauport Cruiselines, or set sail on an excursion aboard The Artemis.  

Discover Cape Ann’s Coastal Towns 

Take a scenic drive through the surrounding towns of: 

  • Gloucester, MA  

  • Rockport, MA  

  • Essex, MA  

  • Manchester-by-the-Sea, MA  

Each destination offers its own unique mix of beaches, historic landmarks, shopping, and dining. 

Where to Stay for a Cape Ann Summer Getaway 

For travelers looking to experience the best of Cape Ann, Beauport Hotel Gloucester offers the ideal coastal home base. Located along the waterfront near Pavilion Beach, the hotel places guests steps from the ocean, minutes from Gloucester’s top attractions, and close to the best dining and activities throughout Cape Ann. 

Enjoy: 

  • Waterfront accommodations  

  • Rooftop cocktails at Birdseye 

  • Easy access to beaches, boating, and downtown Gloucester  

Whether you’re planning a romantic weekend, a family summer vacation, or a coastal getaway with friends, Beauport Hotel Gloucester offers everything you need to experience the best of summer on Cape Ann. 

Plan Your Summer Escape to Cape Ann 

From harbor sunsets and fresh seafood to rooftop cocktails and seaside adventures, Cape Ann offers countless ways to enjoy the season. Start planning your coastal getaway and discover why summer on Cape Ann is unforgettable 

Summer on Cape Ann FAQ 

What are the best things to do on Cape Ann in summer? 
Cape Ann’s top summer activities include visiting Pavilion Beach, whale watching from Gloucester Harbor, exploring Rockport, enjoying waterfront dining, and experiencing rooftop sunsets at Birdseye Rooftop. 

Where is the best place to watch the sunset on Cape Ann? 
Birdseye Rooftop at Beauport Hotel Gloucester offers panoramic views of Gloucester Harbor and is one of the best places to enjoy a Cape Ann sunset with cocktails and live music. 

What are the best restaurants in Gloucester, MA? 
Some of Gloucester’s favorite dining experiences include 1606 Restaurant & Oyster Bar for elevated coastal dining and Seaport Grille for waterfront dining and summer cocktails.