Outdoor Activities

Kayaking in Gloucester

Kayaking in Gloucester

Halibut Point State Park in Rockport

Halibut Point State Park in Rockport

Charity Road Race

Charity Road Race

Father and Sons Deep Sea Fishing

Father and Sons Deep Sea Fishing

Stand Up Paddle Boarding (SUP)

Stand Up Paddle Boarding (SUP)

Adventures at Yankee Fleet

Exciting deep sea fishing, voted best “Hot Tips” by Boston Magazine and #1 in New England by Charter Fishing Magazine.

Connemara Bay Fishing Charters

Saltwater fishing (striped bass, haddock, cod, tuna and more), lobstering and clambake/lobsterbake cruises in and around the waters off Cape Ann.

Charlie’s Charters

Private fishing charter in Gloucester for Stripers, Blues or Flounders

Discovery Adventures Sea Kayaking and Snorkeling

Guided sea kayaking tours and snorkeling on Ipswich Bay, as well as summer programs for children. Kayak instruction and kayak rentals also offered.

Halibut Point State Park

Halibut Point is a uniquely beautiful coastal seascape. Looking seaward on a clear day, the view stretches from Crane Beach in Ipswich to Mount Agamenticus in Maine and the Isles of Shoals off the coast of New Hampshire.

North Shore Kayak Outdoor Center

Kayak rentals and guided tours located on Bearskin Neck in historic Rockport, Massachusetts.

The HarborWalk

Take in the sights and sounds of the harbor and downtown.  Be introduced to this fascinating and storied city.  The HarborWalk will take you along the waterfront, up to City Hall with its famous murals and rosters of men lost at sea, and down a historic Main Street back to the water.  Along the Walk, you’ll find 42 Story Moments that share our history and contemporary culture. Explore Gloucester. Start with the HarborWalk!