Group Travel in Gloucester, MA

About Gloucester, MA

Home to America’s oldest seaport, Gloucester offers rich maritime history, fresh-caught seafood, an active working waterfront, and several of the world’s most beautiful beaches. Enjoy adventures by land, and by sea, and experience the best of New England’s natural beauty on the coast. Gloucester is alive with arts and cultural attractions, theater, museums, boating, events & festivals, award-winning cuisine, boutiques, and a walkable downtown. There is so much to explore!

Group Travel Resources

Discover Gloucester is happy to offer travel planning support. Please email Executive Director Tess McColgan at for more information and support with:

  • Itinerary planning
  • FAM Tours
  • Parking information and motor coach drop zones
  • Public restrooms (Stage Fort Park Visitor Center (Memorial Day – September), Greater Cape Ann Chamber of Commerce)
  • Picnic tables
  • Group admission to local museums, cultural establishments, and group restaurant options

Play on Land

Cape Ann Lanes & Laneside Pub |

Cape Ann Museum |

Gloucester Stage Company |

Hammond Castle Museum |

Maritime Gloucester |

Essex Shipbuilding Museum (Essex) |

Play at Sea

Cape Ann Whale Watch |

7 Seas Whale Watch |

Maritime Heritage Charters: Schooners Ardelle & Isabella |

Schooner Adventure |

Schooner Thomas E. Lannon |

Tours & Charters

Agawam Boat & Fishing Charters |

Cape Ann Foodie Tours |

Cape Ann Cruises |

Charlie’s Charters |

Gloucester Fleet Deep Sea Fishing & Charters |

Tuna Hunter Fishing Charters |

North Shore Adventures |

North Shore Brewery Tours |


1606 Restaurant & Oyster Bar |

Minglewood Harborside |

Mile Marker One |

Seaport Grille |

The Cupboard of Gloucester |

DecKlyn’s |

Woodman’s of Essex (Essex) |


Beauport Hotel |

The Hotel at Cape Ann Marina |

The Emerson Inn (Rockport) |


For more information and coordination support for your group travel to Gloucester, email Discover Gloucester Executive Director Tess McColgan:

“Gloucesterpedia” Fun Facts

  • Gloucester is the largest lobster fishing port in the state of Massachusetts, with over 120 active lobster fishing vessels catching off of our abundant shores, and supplying local restaurants, seafood markets, and food establishments with the freshest lobster available.
  • A variety of aquatic species are caught and supplied through Gloucester’s Working Waterfront, including scallops, clams, bluefin tuna, bass, pollock, halibut, haddock, and more.
  • Gloucester has set the scene for a number of popular films and TV shows: Wicked Tuna on National Geographic, The Perfect Storm, CODA, and Captain’s Courageous to name a few.
  • Gloucester was first settled by English colonists in 1623, making 2023 our 400+ anniversary. The famous Fisherman’s Memorial on Stacy Boulevard, also known as “The Man at The Wheel,” was erected to honor the lives of those lost at sea following Gloucester’s 300th anniversary in 1923.
  • The City of Gloucester is located on the traditional and ancestral homeland of the Pawtucket people and their neighbors the Massachusett, Nipmuc, Penacook, and Wampanoag tribes.
  • Gloucester is home to the oldest continually-operated art colony in the country: Rocky Neck, which is home to dozens of artists and their galleries to this day.
  • Gloucester has more than 5000 acres of green space available to the public for hiking, wildlife, birding, natural beauty, and exploration.
  • During the summer months, there are more than 30 nights of free live music around the city.
  • Gloucester is a popular whale watching destination, with whale watches leaving our harbor daily from April-October. Humpback, Finback and Minke Whales are among the most sighted species off of Cape Ann.
  • Numerous famous innovators and creatives have called Gloucester home, leaving behind historic properties and legacies, including Hammond Castle Museum, The Beauport Sleeper-McCann House, The Sargent Museum, and the Babson Boulders in Dogtown Common.
  • Cape Ann is home to five iconic lighthouses, each of which can be reached by land or sea.