A Great Alternative to the Cape: Exploring the North Shore

Travel Advisor Isabel Smallman walking through vineyards in an all white outfit with a tan hat.
Curated By

Isabel Smallman

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  • Massachusetts

  • Cape Cod

  • Gloucester

  • Active Travel

  • Beaches

  • Couples Travel

  • Coast

  • Laid back

  • Romantic

Boat on the seashore
Curator’s statement

Gloucester, MA, has been an up-and-coming hotspot on Boston's North Shore. Home to America's oldest seaport, this beach town boasts a rich history, as-fresh-as-you-can-get seafood and unbeatable coastal views lined with white sand. An ideal spot from spring to fall, this community comes alive during the warmer New England months and attracts tourists worldwide.

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Where to stay in Gloucester

Beauport Hotel Gloucester

A coastal retreat that harmoniously combines breathtaking ocean views, luxurious accommodations, and New England charm for an unforgettable seaside getaway.

The Hotel at Cape Ann Marina

Experience coastal charm and waterfront beauty at The Hotel at Cape Ann Marina, where picturesque views of the marina, comfortable accommodations and a laid-back atmosphere offer a delightful stay in Gloucester, Massachusetts.

Atlantis Oceanfront Inn Hotel & Breakfast Café In Gloucester, MA

Discover the perfect seaside retreat where stunning ocean views, cozy accommodations and a delicious breakfast café combine to create an unforgettable experience on the picturesque Massachusetts coastline.

Travel Advisor Isabel Smallman walking through vineyards in an all white outfit with a tan hat.

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Things to do in Gloucester

Flags on the seashore

Beaches

Good Harbor - This 1.4 mile beach is very popular with families because there are great tidal pools for swimming, some big waves for body surfing, and a central snack shack with an extensive menu to please everyone. On the far end of the beach is a "Joes on a Roll" food truck that just opened in 2022 to bring beach-goers some of the best lobster rolls and tater tots in town. But BEWARE of the seagulls, they will fly away with it in the blink of an eye. At low tide, beachgoers are able to traverse the sandbar to Salt Island (located just off the beach). You may even see some seals if you're lucky!

Wingaersheek - This 0.6 mile beach is perfect for those who prefer a waveless and quiet beach with sand that stretches far out to reach the ocean as this beach seems to have an unusually long low tide, making it a favorite spot for families with small children. This beach is also a hotspot for finding sand dollars and long walks onto the private side of beach for climbing rocks.

Half Moon Beach - Tucked away at Stage Fort Park, this beach is a small hidden gem of Gloucester that is perfect for a quiet getaway with a snack shack not far away to have yourself a picnic.

I recommend downloading the Blinkay parking app to reserve and pay for your parking space up to 10 days in advance (spaces fill up VERY quickly on Saturdays and Sundays!)

Tours/Parks

Whale Watch - The best whale encounters are just off the Gloucester coast. I recommend Cape Ann Whale Watch or 7 Seas Whale Watch.

Hammond Castle Museum - A medieval castle built in the 1920's that provides a scenic landscape of the Gloucester coastline.

Stage Fort Park - A well-rounded park that offers public tennis courts, a dog park and a hidden beach (Half Moon Beach). This park is perfect for a picnic and area to hang out for live music at night during the summer months.

Halibut Point - This state park and reservation in Rockport, MA, boasts a historic granite quarry overlooking the Atlantic Ocean with trails that are easy to navigate. This is also an incredibly scenic drive which loops Route 127A past Halibut Point and back towards Gloucester. Stop at The Lobster Pool (BYOB) on the ay for some seafood and take in the salt air while you dine at their picnic tables perched along the water's edge.

Ravenswood Park - Miles of trails that take you away from the hustle and bustle of downtown Gloucester.

In addition to these activities, here are some other ideas to keep you busy and curious during your stay:

Day Trips

Salem, MA - Spooky ghost tours, window shopping on the cobblestones of Washington Street and popular museum's that showcase the city's rich history of witchcraft.

Newburyport, MA - The Market Square Historic District is an absolute favorite among tourists to visit for its food trucks, live music and endless streets to explore for shopping and dining.

Boston, MA - Relive American history on The Freedom Trail, soak in the traditional and modern charm of the city, and enjoy some unforgettable food and drink on the Boston harbor-front.

Places to eat & drink in Gloucester

Mussels in the ice

Breakfast

George's Restaurant and Bar - A prominent diner that has lived up to the hype serving huge portions of all-American classics. Be sure to get there early on the weekends to secure a seat! If you would rather sleep in on vacation, order for takeout and bring it along with you to the beach.

Zeke's Place - A casual eatery with a STACKED menu of pancakes, sandwiches, and egg's benedict. There is something to indulge everyone in the group!

Two Sister's Coffee Shop - Tucked away in a relaxing neighborhood corner, this breakfast spot gives a very intimate presence while chef'ing up some hearty meals!

Mom's Kitchen - Between the food, atmosphere, and service, this place makes you feel right at home. I definitely recommend the cinnamon roll drizzled in the sweetest icing.

Willow Rest - An old-fashioned exterior with some of the most satisfying gourmet foods that any foodie would be salivating over. The Morning Sandwich is a popular pick, but the French Toast and Willow's Bennie make you come back for a 2nd, 3rd and maybe 4th visit...

For Coffee Lovers

Castaways Vintage Cafe - A personal favorite, this cafe is right on Main Street serving as a thrifty clothes store as well as a whimsical coffee shop. For those that have a "snapchat eats first mentality," you will get some aesthetically sweet shots for your camera roll. Delicious cold brews, homemade baked goods and açai bowls packed with all the nutrients you need for the perfect summer bod.

Lone Gull Coffee House - A quick walk up from Castaways, Lone Gull is a cozy space with excellent coffee and an assortment of pastries to spice up your morning.

Cape Ann Coffees - A simple coffee shop for a quick grab and go (one of the few spots with a Drive Thru!) has a fantastic selection of coffee and pastries to indulge in.

Lunch & Dinner

Mile Marker One - Situated at the Cape Ann Marina Resort, offers both indoor and outdoor seating with picturesque views of the Annisquam River. This restaurant is an iconic summer spot. With its chic deck seating and U-shaped bar, cocktails are being crafted all day long to wash down creative and innovative takes on veggie/meat/seafood plates.

If you love National Geographic's TV Show "Wicked Tuna," head to the outside deck for lunch and catch a glimpse of these famous fishing boats (if you're lucky, you might even recognize one of the crew members!).

Causeway Restaurant - A Gloucester staple. They do not skimp you on quality or quantity of seafood! So if you're looking for a grab and go picnic, head here for some stacked platters of joy.

The Azorean Restaurant and Bar - Authentic Portuguese cuisine that boasts a variety of flavors and menu options.

Virgilios - A family-owned bakery famous for its authentic sandwiches and pastries.

Surfside Subs - A grab and go pizza for lunch or sunset on the beach. This restaurant has drawn in many celebrities for spinning up some of the biggest pizzas and an impressive variety of flavors. But beware of the seagulls...they love pizza too.

If you're craving a sweet after the salty, Dairy Maid next door has a novel of ice cream flavors to choose from and their portion sizes are generous.

Tacos Lupita - If you're craving some Mexican cuisine, head to Main Street for some of the most authentic tacos and enchiladas in the area. Very affordable and energetic atmosphere!

Talise - A small menu that changes depending on which local ingredients are available. Tucked away in a residential area, its interior is as appealing as the quality of its food. With views overlooking the Annisquam, you will be waited on with the best service and recommendations of staff members. (Make a reservation at least one week in advance!) Dinner only.

Short & Main - A farm-to-table bistro that serves up classic flavors of wood fired pizza, freshly shucked oysters and crafty cocktails by some of the best service staff on Main Street. Dinner only.

Tonno - At the end of Main Street and not one to miss, this Italian menu details some of the best local ingredients (especially the seafood!). Offers both indoor and outdoor seating. Dinner only.

Franklin Cape Ann - A cozy ambiance with an intimate feel in a warmly lit atmosphere serving up classic seafood and meat dishes right off Main Street. Dinner only.

Passports Eatery and Wine Bar - A simple and modest interior serving up American dishes with an international flare. A popular option right on Main Street for both sit down and take out.

For those furry friends who also want some time to explore this picturesque beach town...Crab Beach by Stage Fort Park has a section of beach exclusively for dogs to swim and soak up the sun:)

Travel Advisor Isabel Smallman walking through vineyards in an all white outfit with a tan hat.

Travel Advisor

Isabel Smallman

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Looking for more travel inspiration? Check out my guide, Foodie's Guide to Savannah.

This guide is part of our ongoing series on travel to Massachusetts.