The best city hikes and walks around Gloucester

The Gloucester Harborwalk is a pedestrian pathway along the shores of the America's oldest seaport. This particular section of the Harborwalk is just blocks from Main Street and features amazing views over Gloucester Harbor. Along the Harborwalk there are 42 stops marking important buildings, monuments, vista, or narrating the history of the area. Here is a link to a website that has a self-guided tour of the Harborwalk, detailing the various sites and stops along the way: harborwalk.gloucester-ma.gov

The Gloucester Fishermen’s Wives Memorial was unveiled in 2001, and is a reminder of the backbone of Gloucester’s fishing community. It represents families waiting for the safe return of their loved ones from the sea.

Stage Head was a fishing stage, named in 1624. The first fort was built here in 1635. Today it's a state park with two beaches, the reconstructed civil war fort and other leisure infrastructure.

Sunset Hill, or Pole/ Poles Hill, is an 105 foot summit that is a hidden-gem in Gloucester. From the summit, which is an open, granite rock outcropping, you get great views through the spare trees to the water. The hill itself is ringed with large glacier erratic boulders (which might have been a part of a Native American Solar Observatory) and rests between two rivers. There is a pleasant network of trails to and around the hill, but they can be a little overgrown in the springtime.

Overlooking one of the basefall fields in Stage Fort Park is a large bronze plauque on a huge grantite cliff that reads: "On this site in 1623, a company of fishermen and farmers from Dorchester, England, under the direction of Rev. John White, founded THE MASSACHUSETTS BAY COLONY. From that time the fisheries, the oldest industry in the commonwealth, have been uninterruptedly pursed from this port. Here in 1625, Gov. Roger Conant, by wise diplomacy, averted bloodshed between contending fractions, one led by Myles Standish of Plymouth, the other by Capt Hewes, a notable exemplification of arbitration in the beginnings of New England. Placed by citizens of Gloucester, 1907." This plaque speaks to the rich history of the area and believe it or not, you can sometimes see rock climbers ascending the rock faces next to the historic plaque!

Stage Fort Park is a park in Gloucester with a rich history. Gloucester's Visitor and Welcome Center and a reconstructed Civil War fort, Stage Fort, are both within park grounds. The park also has a playground, picnic benches, baseball fields, a dog park, and a bathhouse. There are two beaches in the park, Cressy and Half Moon Beach, stunning viewpoints, as well as a huge granite stone (with a plaque) thought to have been used by Native Americans, and cannons leftover from a Civil War-era fort. There is a privately owned seasonal restaurant, The Cupboard of Gloucester, where you can order fried clams and sandwiches.

Along the Harborwalk near the famous Stage Fort Park is the Gloucester World War II Memorial, dedicated to the citizens of Gloucester who fought and died in WWII.

The Gloucester Fisherman's Wives Memorial is just short distance west of the Gloucester Fisherman's Memorial and is dedicated to the wives, mothers, sisters, and children of fishermen and the sacrifices they made on land as their husbands, sons, and brothers worked, and sometimes died, at sea.