Miles of rocky coastline peppered with lush green spaces, sandy beaches, and gorgeous vistas make Gloucester, Massachusetts, a perfect weekend getaway destination. Cape Ann newbies will be enchanted by the kick-back coastal vibe, and seasoned guests who have visited Gloucester before will head straight to their favorite beaches.
Gloucester’s history was built on the fishing industry, and it is still a thriving seafaring community.
Note: Some information in this piece was obtained during a sponsored press trip, but all recommendations are my own.
Things To Do In Gloucester
Gloucester’s northshore location makes it a great playground for escaping the workday worries, letting you shake them off for a few days or several weeks. The craggy coastline and numerous inlets, bays, and rivers offer fabulous on-the-water activities to keep you as busy or as relaxed as you choose.
Beaches Rule In Gloucester
The beach scene is what brings everyone to Gloucester for their summer vacation. You can read our Gloucester beach guide here.
Pro Tip: Beginning with the 2022 beach season, a new online non-resident beach parking reservation system will help reduce and streamline beach traffic. Yodel, a parking management app, allows non-resident beachgoers to reserve and pay for their parking space at Gloucester beaches up to 10 days in advance eliminating the first-come, first-serve parking system.
Good Harbor Beach
Good Harbor Beach is a welcoming soft, sandy beach. It is a popular toes-in-the-sand spot for Gloucester visitors. At low tide, the beach is long and wide with plenty of room for everyone’s blanket.
Wingaersheek Beach
Wingaersheek Beach on the northern section of Gloucester is a gorgeous wide sandy beach punctuated by enormous boulders at low tide. It is out of the flow of downtown Gloucester Harbor, making it a wonderful spot to spend the entire day.
Pavilion Beach
Pavilion Beach is famous for the “Greasy Pole Challenge” held each year during the St. Peter’s Fiesta in June. St. Peter is the patron saint of netmakers, shipbuilders, and fishermen with this 5-day celebration that honors the fisherman saint.
Half Moon Beach
Half Moon Beach is a small, crescent-shaped beach accessed in Stage Fort Park. The rough sandy beach is reached by traversing carved stone steps leading down to the water.
Cressy’s Beach
Cressy’s Beach is another rocky beach in Stage Fort Park and offers wonderful views of Gloucester Harbor.
Tour Hammond Castle Museum
In the 1920s, John Hays Hammond, Jr. decided to build a medieval castle on the Gloucester coastline, now known as Hammond Castle Museum. During the ‘20s and ‘30s, Hammond made several trips to Europe to obtain remnants of crumbling castles securing stone archways, fireplaces, and religious artifacts. Hammond’s castle home is a showcase of eclectic pieces including the monstrous pipe organ that dominates one end of the Great Hall.
Known for his inventions and securing over 400 patents in his lifetime, Hammond was an engineering genius. He is renowned for his work with radio control equipment. The castle rooms showcase a life of wealth and eccentricity, leaving guests to wonder what it was really like to live in a modern medieval castle.
Explore Beauport, The Sleeper-McCann House
A National Historic Landmark and summer home of Henry Daivs Sleeper, Beauport is a decorator’s masterpiece. Sleeper was an interior designer who loved beautiful things. The rambling mansion is a series of one showstopping room after another.
The casual dining room with its long table and mismatched chairs, painted a seafoam green set off by the expansive windows overlooking the coastline, sits waiting for a party. You can envision the guests in light summer garb sipping sparking libations and nibbling on delicate appetizers while enjoying lively conversation. Conversely, the China Trade Room, decorated with Asia-inspired pieces including hand-painted Chinese wallpaper, gives off a completely different vibe.
Visiting the Sleeper-McCann House is a must for designers and others seeking a spark of inspiration. The McCann family purchased Beauport after Sleeper’s death and kept the home design unchanged.
Picnic At Stage Fort Park
Stage Fort Park is an inviting green space in the heart of Gloucester. Within the park, you can swim at Half Moon and Cressy’s Beaches, climb the enormous rocks for an impressive harbor view, and explore the remnants of the old fort. The park has a large number of picnic areas, fields, and walking paths for enjoying the outdoors. There are even on-site bins where you can deposit the coals from your barbeque — you need to bring your own grill.
Sail Away For A Whale Watching Trip
If you have never been out to Stellwagen Bank National Marine Sanctuary on a whale watching excursion, then it is time to put this on your must-do list. It is the spot in the northeast to view our whale population.
Several companies offer excellent trips including 7 Seas Whale Watch and Cape Ann Whale Watch.
Scope Out A Wicked Tuna Boat
National Geographic’s TV show Wicked Tuna is filmed out of Gloucester. Now in its 11th season, it has become a classic reality, one-bluefin-tuna catch at a time show.
Pro Tip: Want to catch a glimpse of one of the fishing boats on the show, or perhaps run into your favorite onscreen fisherman? Some of the show’s tuna boats are docked at Cape Ann’s Marina Resort.
Snap A Photo With The Fisherman
The Fisherman’s Memorial is synonymous with Gloucester. The patinanted statue gazes out to Gloucester Harbor intent on bringing his ship safely home. It is a poignant reminder of the perilous life of fishermen out on the ocean. Designed by sculptor Leonard F. Craske, the statue pays homage to the Gloucester fishermen lost at sea.
Restaurants In Gloucester
Fresh seafood, prepared simply, is a gift from the kitchen. You will find many dining options in the Gloucester area. Below are three favorites.
1606 Restaurant And Oyster Bar
When you are looking for a fine-dining experience with a beautiful ocean view, the 1606 Restaurant and Oyster Bar in the Beauport Hotel is an excellent choice. The dining room is dressed in elegant crystal and ocean blues bringing the brilliant colors and sparkle of the harbor indoors.
Starters set the tone for every meal, and the options here are perfect. The pan-seared crab cake with red cabbage and apple slaw is not only delicious, it is healthy too. Of course, the chowder is creamy and delicious. The fish fry and the baked haddock casserole shine on the entrée menu.
Mile Marker One Restaurant
When you put a modern twist on traditionally-classic dishes, you set the bar high. At the hip and casual Mile Marker One Restaurant, they offer the perfect storm: delicious food and outstanding views.
Nestled in the heart of the marina on the Annisquam River, you can watch the busy harbor comings and goings as you happily munch on delectable delights from the local waters. Starters like the sauteed mussels with sausage and garlic in a flavorful broth, or the carmelized pear and fresh burrata salad with greens and bacon are loaded with flavor. The signature horseradish-crusted haddock topped with super crispy leeks resting on herb mashed potatoes rivals the seared local tuna served with a mango, avocado, and macadamia nut salad and a silky cashew sauce. Add a chilled bottle of wine and you have marina dining perfection.
During the cooler seasons — everyone but summer — they have custom marina-made igloos for a semi-al fresco dining experience. The heated tents have window views of the harbor and create a private dining room for each party. The unique dining experience, enhanced by the water views, is the perfect addition to your Gloucester getaway.
George’s Restaurant And Bar
When you are in the mood for a charming neighborhood spot, George’s Restaurant and Bar fits the bill. Slightly off the main tourist area, George’s is open for breakfast, lunch, and dinner.
Their breakfast and brunch menu is extensive and hearty. There are eggs Benedict and scrambled, omelets, pancakes, and French toast options with something for everyone. The specialties like their buttermilk biscuits and gravy served with three eggs will feed the hungriest diner. A more healthful specialty, George’s Loaded Avocado Toast is a huge plate of avocado, bacon, spinach, onions, and two perfectly poached eggs topped with a tangy balsamic drizzle — it keeps guests coming back again and again.
Hotels In Gloucester
The key component to choosing a spot to rest your head in Gloucester is the view. Find a spot that offers you beautiful sunsets and sunrises that works for your weekend budget.
Cape Ann’s Marina Resort
Just outside of the hustle of the downtown area is Cape Ann’s Marina Resort. Cozy rooms with a coastal vibe are on top of the waterfront action. From the extended deck, you can dreamily watch the harbor boats come and go, hear the chatter of local fishermen, and look on enviously at the yachts slicing through the local waters.
Enjoy a relaxing long weekend stay and a room with a gorgeous view, perfect for relaxing after a day at the beach. You can dine on-site at Mile Marker One and then stroll along the docks to watch the picturesque sunsets on the rippling water.
The resort is undergoing a complete renovation of their guest rooms (several under restoration at a time), ushering in a modern and casual beachy resort feel.
Rental Home Near The Beach
When you are vacationing with extended family, a gang of friends, or your besties, this new home with private beach access is a great option. The 3,000 square foot house sleeps eight and offers amazing views, cozy nesting areas, and gathering spaces.
Cape Ann’s Gorgeous Gloucester
Gorgeous Gloucester on Cape Ann’s coastline is an escape destination where your daily dilemma is which beach and which restaurant. You will love the easy, laid-back atmosphere coupled with soothing on-the-water activities and the freshest local catch.
Don’t just stop at Gloucester. See everything that Massachussetts has to offer:
