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Rockport and Gloucester 2 Day Itinerary

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Fishing Boat on Gloucester Harbor | Rockport and Gloucester MA 2 day Itinerary
Fishing Boat on Gloucester Harbor

There is much to do in the coastal New England towns of Rockport and Gloucester, Massachusetts. The neighboring communities are full of fishing wharves, galleries, and beaches. In Rockport, you will find a village of artists and crafters that will charm and engage you. In Gloucester, the hard working community of fishermen and merchants will impress you with their devotion to the sea. Our Rockport and Gloucester, MA 2-day itinerary (with map) will you help fit in all the fun.

Lunch on the Water | Rockport and Gloucester MA itinerary | New England travel blog
Lunch on the Water

A unique quality to the area is how close you can get to its fishing and arts communities. Walking the wharves you can meet local lobstermen, chat with the fishermen from National Geographic’s Wicked Tuna, and/or meet the artist who created the watercolor you are considering purchasing. The region is beautiful, walkable, and accessible.

Jodrey State Fish Pier | Gloucester Harbor | New England Travel Blog
Jodrey State Fish Pier

We hope you enjoy our Rockport and Gloucester MA itinerary. For more information on the area’s weather, hotels, restaurants, and things to do see our Rockport and Gloucester Travel Guide.

Rockport and Gloucester MA 2 Day Itinerary with Map At A Glance
Blue Collar Lobster Co. | Rockport and Gloucester MA 2 Day Itinerary | New England Travel Blog
Blue Collar Lobster Co.

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Best Time to Visit Gloucester and Rockport MA

This 2-day Rockport and Gloucester, MA itinerary can be completed on a weekday or weekend. The busiest travel times for the area will be weekends from late June until mid-September. During this period, reservations for lodging and finer restaurants should be made in advance. The quietest months of the year will be January through March when many seasonal businesses are closed (but rates are cheaper and parking is plentiful).

Gloucester Harbor Walk | Rockport and Gloucester MA Itinerary | New England Travel Blog
Gloucester Harbor Walk

The itinerary will work well with lodging in Rockport or Gloucester. To minimize driving, we recommend staying in the Rockport seaport area. For Day 1 of the itinerary, we have included a Gloucester Harbor walking map for your reference.


Gloucester Harbor Walk

Gloucester Harbor Walking Map - Google
Gloucester Harbor Walking Map - Google

Day 1: Walk Gloucester

Stage Fort Park, Down Town, Waterfront, Jodrey State Fish Pier

Begin your day with a visit to Stage Fort Park in Gloucester, MA. At the top of the hill there is a Visitor’s Center with bathrooms. Stock up on maps, then walk to the gazebo for fine views of the Atlantic Ocean. Find Tablet Rock, and locate the plaque commemorating Gloucester as the first permanent settlement in the colony of Massachusetts.

Gazebo Stage Fort Park | Gloucester Harbor | Gloucester MA itinerary
Gazebo Stage Fort Park

From here, hike the wooded trails behind Tablet Rock that have stunning look-outs over Gloucester Harbor. Locate Half Moon Beach. Then, explore the remains of old cannons and guns scattered over the hills.

Cannons and Trails | Stage Fort Park | Gloucester 2 Day travel itinerary
Cannons and Trails | Stage Fort Park

Next, head into downtown Gloucester. Park near the waterfront (try I4C2 or the City Lot). Stroll one block inward to Gloucester’s quaint Main Street. Peruse the Dogtown Bookstore, Menage Gallery, and the many shops selling toys, martinis, antiques, silver jewelry, and so much more.

Dogtown Books | Gloucester MA Itinerary | Gloucester Harbor walking map
Dogtown Books | Gloucester MA

From Main Street, take one of the lanes that leads back to the waterfront (Rogers Street). Locate the entrance to Harbor Loop Road by Walgreens and Rhea Pizzeria. Next, walk Harbor Loop Road past the harbor master’s office and Coast Guard station.


Back on Rogers Street, trek to the Gloucester House Restaurant. Walk behind the restaurant to explore the city’s working harbor. In this area, you will find the historic Schooner Thomas E Lannon as well as Fat Tuna Charters and Dave Marciano’s boats (from Nat Geo's Wicked Tuna fame). After viewing this area, walk the Gloucester Fishermen’s Wharf.

Gloucester House Restaurant | Rockport and Gloucester MA itinerary | New England Travel Blog
Gloucester House Restaurant

Take your time discovering the boardwalks and piers of Gloucester Harbor as you make your way toward Commercial Street. Trekking along Commercial, look for the Rockport and Mortillaro Lobster companies. Further along, see the Boston Fish Market and Cape Pond Ice Company. These are working docks, but many of the areas are open to the public where you can watch boats load and unload their catches. The Cape Pond Ice has a company store.

Boardwalk | Gloucester Harbor Walk | Rockport and Gloucester MA Itinerary
Boardwalk Gloucester Harbor

Retracing your steps along Commercial Street, take Western Ave to Stacy Boulevard. Then, cross onto the beautiful Stacy Avenue Esplanade paralleling Gloucester Harbor. As you walk, you will have gardens on side, and gorgeous Gloucester Harbor on the other. The esplanade takes you to the Gloucester Fisherman’s Memorial and Gloucester Fishermen’s Wives Memorial.

Gloucester Fisherman's Memorial | Rockport and Gloucester MA 2 day itinerary
Gloucester Fisherman's Memorial

The monuments pay tribute to the thousands of Gloucester fishermen who have lost their lives at sea, and to the families who were left behind. A part of the city’s proud fishing heritage, the memorials are a sobering reminder of the risks involved in the deeply ingrained Gloucester fishing culture.

Gloucester Fishermen's Wives Memorial | Gloucester Harbor Walking Map
Gloucester Fishermen's Wives Memorial

If you did not stop for lunch at one of the many restaurants offering fresh-off-the-boat seafood, retrieve your vehicle and make your way across the Gloucester drawbridge to Essex Avenue. Drive to the Cape Ann Marina Resort. Here, you can have lunch at the Mile Marker Resort, walk the marina, and try to spot one of the boats from National Geographic’s Wicked Tuna hit series. There is also a Wicked Tuna gift shop onsite.

Wicked Tuna Boats | Cape Ann Marina | Gloucester MA Itinerary | New England Travel Blog
Wicked Tuna Boats | Cape Ann Marina

The next stop on the itinerary is the Jodrey State Fish Pier. Park the car and explore this 8-acre site. On the complex there is a seafood processing plant, fishing boat docking facilities, ship berths, and a marina. Away from the bustle of downtown, it is easy to strike up conversations with local fishermen. On our last trip a dock worker pointed out the Angela + Rose fishing boat cruising past the pier (the boat used in the Academy Award winning movie, CODA).

Angela + Rose Fishing Boat  (CODA) | Gloucester 2 Day Itinerary with Map
Angela + Rose Fishing Boat (CODA)

Head to your hotel to check-in and freshen up. In the late afternoon, make your way to downtown Rockport MA. We like to park in the lot by T-Wharf. Take pictures of the iconic Motif #1 red fishing shack (said to be the most photographed and painted building in the world). Then, walk along the waterfront until reaching Main Street.

Randy at Motif #1 Rockport Harbor | Rockport and Gloucester 2 day Itinerary with Map
Randy at Motif #1

Spend the next hours exploring the art galleries, shops, and seaside business of downtown and Bearskin Neck. Bearskin Neck is a waterfront area off of Main Street that is filled with a maze of weathered New England buildings lining narrow lanes. The buildings are an eclectic mix of beach shops, upscale boutiques, cafes, and galleries (there is even a psychic’s shop). The artists who create many of the paintings, jewelry, textiles, and ceramics are often on hand to speak with.

Bearskin Neck Shopping | Rockport and Gloucester MA 2 Day Itinerary | New England travel
Bearskin Neck Shopping

Have dinner on in Rockport. We suggest Roy Moore’s Fish Shack (Dock Square) or My Place by the Sea (Bearskin Neck). Both have great seafood and views of the water. After dinner walk the Bearskin Neck Jetty.

Bearskin Neck Jetty | Rockport and Gloucester MA 2 Day itinerary with map
Bearskin Neck Jetty

Day 2: Walk Rockport

Walk Rockport’s Front Beach. Brunch. Whale Watch or Schooner Cruise.

In the morning, sleep in. Then, walk Front Beach behind Rockport’s Main Street or Half Moon Beach in Gloucester’s Stage Fort Park. Brush off the sand, and have brunch. For the remainder of the day get out on the water. Do a whale watch, take an historic cruise on the Thomas E Lannon, or book a trip one of the many sailing catamarans. As you cruise by islands, small New England towns, and lighthouses you are apt to see whales, seal harbors, and seabirds.

Half Moon Beach, Stage Fort Park | Rockport and Gloucester MA 2 Day Itinerary
Half Moon Beach, Stage Fort Park

Don’t forget your sunscreen and water shoes, Laura and Randy

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Rockport Harbor and Motif #1 | Rockport and Gloucester MA Itinerary | New England Travel Blog
Rockport Harbor and Motif #1

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