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Rockport and Gloucester MA Travel Guide

Broadway Wharf, Motif #1, Rockport MA | New England Travel
Motif #1 Rockport

Rockport and Gloucester, Massachusetts are neighboring towns on the New England coast. Rockport has a postcard-worthy harbor town full of art galleries and specialty shops. Next door, Gloucester is home to a robust commercial fishing fleet. A trip to these Cape Ann communities means enjoying lots of ocean vistas, walks along wharves, and fresh seafood. Our Rockport and Gloucester MA travel guide has information on the best time to go, how to get there, and where to eat, sleep and shop.

Cape Ann Marina | Rockport and Gloucester MA Trave Guide
Cape Ann Marina, Gloucester
Rockport and Gloucester MA Travel Guide At A Glance | Travel Blog

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Blue Collar Lobster | Gloucester MA Travel Guide | New England Travel
Blue Collar Lobster, Gloucester MA


Rockport, MA

On the Cape Ann peninsula, Rockport, MA is surrounded on three sides by the Atlantic Ocean. The town's population balloons every summer when visitors arrive to experience its quintessential New England-ness. The appealing coastal essence stems from Rockport’s charming harbor, Dock Square, and Bearskin Neck village.

Roy Moore Lobster Co., Bearskin Neck | Rockport MA | New England Travel
Roy Moore Lobster Co., Bearskin Neck

Rockport’s roots can be traced back to the 1600s when colonists first settled the fishing community. Over the years the area developed into a commercial trade port, an international granite supplier, an artist’s colony, and a thriving summer community. Today, evidence of the town’s journey is seen in its sea shanties, saltboxes, and stone foundations as well as in its artisan food, fashion, and art scene.

Ocean Reporter Rockport | Things to do in Rockport MA | Travel Blog
Ocean Reporter Rockport
Gloucester, MA

The lifeblood of Gloucester, MA is the sea. Gloucester (rhymes with “Foster”) has a storied fishing culture. The city is America’s oldest active working waterfront. For over 400 years, Gloucester men and women have looked to the Atlantic Ocean for their livelihoods. The city supports one of the largest commercial fishing fleets in New England.

Boat Yard, Gloucester MA Travel Guide | New England Travel Blog
Boat Yard, Gloucester MA

If Rockport is a place where people shop and stroll, Gloucester is a place where people work. There is purpose in Gloucester, and deep ties to the sea. These realities are apparent when you view the city’s busy harbors, diverse fishing fleet, draw bridges, and fish processing factories.

Princess Laura Fishing Trawler | Jodrey State Fish Pier | Gloucester MA Travel Guide
Princess Laura Fishing Trawler

Gloucester does a good job of helping visitors learn about its history. Around town visitors will find a number of museums, monuments, and parklands. There is no better way to immerse in Gloucester’s fishing culture, though, than by walking its marinas and wharves.

The Man At Sea - Gloucester's Fisherman's Memorial | Gloucester Travel Guide | New England Travel Blog
Gloucester Fisherman's Memorial

Out on the docks you can see industrial cranes unload commercial fishing boats, observe lobstermen scoot back and forth across the harbor, and watch fishing charters unload huge bluefin tuna. Nat Geo’s “Wicked Tuna” is filmed here. The show has brought viewers into the lives of real fishing families, and been a boon to the city’s tourism.

Wicked Tuna Gear at Gloucester House | Shopping Gloucester MA | New England Travel Blog
Wicked Tuna Gear at Gloucester House


Gloucester is about 33 miles northeast of Boston, and 250 miles east of New York City. Neighboring Rockport is 40 miles northeast of Boston. Gloucester and Rockport can be easily accessed by auto (Route 127/127A), bus (the Cape Ann Transportation Authority), or train (commuter rail from Boston’s North Station).

Beach Houses | Gloucester MA | New England Coast Travel Blog
Beach Houses


Rockport and Gloucester share a maritime climate. It is cloudy and windy many days throughout the year. Summers are comfortable with temperatures rarely rising above 79’ F. Winters are cold with frequent precipitation (snow, sleet, and rain), with temperatures rarely falling below 23’ F.

Boats Docked | Cape Ann Marina | Rockport and Gloucester MA Travel Guide
Boats Docked | Cape Ann Marina


Late spring, summer, and fall (May through October) are the best months to visit the area. May, June, and October will have temperate weather and less crowded conditions. July and August will have the warmest weather, greatest crowds, and most events, fairs, and festivals.


Coastal New England weather is notoriously changeable. Dress in layers. In summer, short sleeves with a light jacket and rain gear is appropriate. In winter, have parkas/boots/hats/gloves on hand.

Coast Guard | Jodrey State Fish Pier | Gloucester MA Travel Guide
Coast Guard | Jodrey State Fish Pier


Check out these Rockport MA Beaches and Parks
  • Front Beach: (Rockport Village) On Sandy Bay in the village of Rockport (behind the Shalin Liu Performance Center) find a small, sandy beach. Great for tide pooling and hunting sea shells.

  • Back Beach: (Rockport Village) Opposite the rocky expanse from Front Beach. Rocky/pebbly beach with pockets of sand and great views.

  • Long Beach: (Old County Road) Traditional sandy beach with retaining wall lined by summer cottages. Views of Thatcher Lighthouse. (No onsite public parking.)

  • Halibut Point State Park: (4 Gott Avenue) State Park with trails to hike, picnic grounds, ocean views, rocky ledges, and information on area’s ties to World War II.

Ledges | Halibut Point State Park | Rockport MA Beaches | Rockport and Gloucester Travel Guide
Ledges | Halibut Point State Park
Check out these Gloucester MA Beaches and Parks
  • Good Harbor Beach: (99 Thatcher Rd) Small beach with surrounding marshes and dunes. Good for swimming.

  • Half Moon Beach: (Stage Fort Park) Small sandy beach in Stage Fort Park. Beautiful views of rocky cliffs and Gloucester Harbor. Close to park’s picnic grounds and playground.

  • Stage Fort Park: (24 Hough Ave) Expansive city park located next to town. Great views of Gloucester Harbor with two beaches, hiking/biking trails, picnic grounds, ball fields, tennis courts, dog park, and a large Visitor’s Center.

Half Moon Beach at Stage Fort Park | Gloucester MA Beaches | New England Travel Blog
Half Moon Beach at Stage Fort Park


Tourism is a major industry in Rockport and Gloucester. The towns have many hotels, motels, inns, and resorts at a variety of price points. Expect to pay in the $150-350.00 range for in-season lodging. Accommodations will cost more the closer to the seashore you book. Book well in advance for accommodations needed in June through September.

Bearskin Neck Motor Lodge | Rockport MA Hotels | New England Coast
Bearskin Neck Motor Lodge


Many great options. Try these fan favorites:

  • Roy Moore Lobster Company: (21 Dock Square) Well-loved, long-time regional seafood restaurant with picnic tables overlooking the water. Also, has take-out shack on Bearskin Neck.

  • Top Dog: (2 Doyles Cove Road) Hot dog shack with a fun dog-themed menu as well as other regional favorites (fired clams, mac and cheese, chicken fingers).

  • My Place By the Sea: (68 Bearskin Neck): Located at the tip of Bearskin Neck, this restaurant (and ice cream store) serves regional seaside favorites (chowder, lobster rolls, and salmon sandwiches) with a deck and ocean view that cannot be beat. Takes same day reservations.

Bearskin Neck Bistro | Restaurants Rockport MA | New England Travel Blog
Bearskin Neck Bistro, Rockport MA


Many great options. Try these fan favorites:

  • Gloucester House: (63 Rogers St) Dine-in seafood restaurant on the historic 7 Seas Wharf. Great harborside views and parking. Fun general store selling Wicked Tuna gear.

  • Mile Marker One Restaurant: (73 Essex Ave) Waterfront dining at Cape Ann Marina Resort. Dine in menu features seafood, steak, and salads. Eat inside or out. Store selling Wicked Tuna gear onsite.

  • Virgilio’s Bakery: (29 Main Street) Bakery offers cut to order meats on freshly baked bread and an assortment of delicious cannoli, cakes, and other pastries.

Mile Marker One | Restaurants Gloucester MA | Things to do in Gloucester MA
Mile Marker One Restaurant | Gloucester


Rockport MA is famous for its extensive shopping options. Whether shopping for inexpensive souvenirs or craftsmen-quality pieces there is something for everyone. Park in the Rockport Village area. Shop Mt. Pleasant Street, Main Street, Dock Square, Bearskin Neck, Broadway, Bradley’s Wharf, and offshoot streets. There are few chain store in this area.

Glassblowing | Shopping Rockport MA | Rockport and Gloucester MA Travel Guide
Glassblowing Shop, Rockport MA


Gloucester MA has a vibrant Main Street in the downtown area. Stores carry an eclectic selection of antiques, crafts, books, and specialty foods. Running parallel to Main Street one block over, Rogers Street is lined with restaurants and shops catering to the fishing and tourist trade such as whale watches and charter fishing boats. There are few chain stores in this area.

Silversmith & Toy Store | Main St., Gloucester | Shopping Gloucester MA
Silversmith & Toy Store | Main St., Gloucester


  1. Go art gallery hopping for paintings, textiles, ceramics, and sculptures. Rockport has over 30 galleries. Gloucester has the Rocky Neck Art Colony just outside of town.

  2. Walk Gloucester’s Stacy Avenue seaside esplanade to view the iconic Gloucester Harbor, the Gloucester Fisherman’s Memorial, and the Fishermen’s Wives Memorial.

  3. Indulge in a few hours of retail therapy at Rockport’s Bearskin Neck shopping district.

  4. Walk Gloucester’s Jodrey’s State Fish Pier and watch the fishermen at work.

  5. Do a photoshoot of Rockport’s iconic Motif #1 (red fishing shack) while wandering Bradley and T-Wharf.

  6. Explore the haunts and hangouts of the National Geographic’s hit series Wicked Tuna by exploring Gloucester’s Cape Ann’s Marina Resort, 7 Seas Wharf, and Smith Cove on Rocky Point.

  7. Walk the beach looking for sea shells and sea glass (see above for area beaches).

  8. Tour Gloucester’s Hammond Castle Museum.

  9. Get out on the water with a sunset sail, schooner cruise, or sea kayaking.

  10. Park in Gloucester’s Eastern Point Lighthouse lot and walk the breakwater for great views of the Coast Guard run lighthouse.

  11. Visit Rockport’s Halibut Point State Park for hiking, picnicking, and ocean vistas.

  12. Drop in at Gloucester’ Cape Pond Ice Factory and Gift Shop. In summer, take a tour.

  13. Go on a whale watch or sign up for a fishing charter.

  14. Catch a show at the Shalin Liu Performance Center in downtown Rockport.

  15. Spend the day in Gloucester’s Stage Fort Park where families can hike, bike, hang out at the beach, play on playground, basketballs courts, and ball fields with panoramic ocean views.

Lobster Traps | Gloucester MA Travel Guide | New England Travel Blog
Lobster Traps | Gloucester MA

Have fun getting to know Rockport and Gloucester, Laura and Randy

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Risky Business Fishing Boat | Rockport and Gloucester MA Travel Guide
Risky Business Fishing Boat


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