Outdoor Adventure Guide
Gloucester is a natural playground for anyone who loves to explore. Miles of rugged shoreline, quiet coves, and open ocean offer endless ways to get out on the water, while forested trails, conservation land, and sweeping coastal overlooks make hiking and biking just as rewarding. It’s a place where you can paddle at sunrise, wander through green space in the afternoon, and end the day watching the light change over the harbor. The Apartment at Green Landing sits right in the middle of it all, giving adventurers an easy home base to reach beaches, trailheads, and waterfront access points in every direction.
Back to GuidebooksGet on the Water
Gloucester is known as America's Oldest Seaport. Today it has unparalleled access for ocean adventurers:
Sail on an Authentic Schooner
The 'Schooner' was invented in Gloucester in 1713. Today, you can sail on the official Flagship of Gloucester - the 'Schooner Adventure'
Learn more here.
Fish with Gloucester's Iconic Fishermen
Get a taste of Gloucester's legacy on a deep sea fishing excursion. ('The Perfect Storm' is not included, but you might see the cast of 'Wicked Tuna').
Learn more here.
See the Whales at Stellwagen Bank National Marine Sanctuary
Take a half-day voyage with local expert naturalists and see marine life up close. Daily trips depart from only minutes away.
Learn more here.
Surf or Paddleboard with a Local Expert
Rent equipment, take a lesson, or join tour with a local expert in Gloucester. An on-the-water pick up location at Pavilion Beach is approximately 1 mile away.
Learn more here.
Rent Fishing Equipment Locally
Seasick? No Problem! Plan ahead and rent what you need to fish around the shores of Cape Ann at your leisure.
Learn more here.
Kayak the Annisquam River
Join a guided tour of the Cape Ann Coastline, or rent a kayak and have it delivered to the public landing of your choice.
Learn more here.
Our Favorite Hikes
Plot a different course and explore Gloucester's over 5000 acres of public greenspace. These are our favorite suggestions:
For more options, we suggest visiting the Essex County Greenbelt Website. All of their properties are available to locals and visitors, completely free of charge and without a membership.
Moderately Challenging:
A One-Of-A-Kind Hike through Dogtown (an abandoned village with a history)
Dogtown is a historic woodland spanning five square miles. As the colonial population shifted toward the coast, the settlement of Dogtown was abandoned, leaving behind cellar holes, stone walls, and legends of purported witches and ghosts. This is also the location of the Babson Boulder Trail, which features inspirational (and sometimes strange) phrases carved into the granite boulders of Gloucester.
Our Tip: Bring or download a trail map beforehand. It is large and easy to get turned around.
Learn more here.
Less Challenging:
A Short Hike to a Less-Traveled Beach
Avoid the crowds and take a short (approximately 900 yards each way) hike through the protected land of Coolidge Reservation to a less traveled beach. Follow the signs for Grey Beach to find yourself at a secluded but public section of a mostly privately-owned beach.
Our Tip: Pack light and get there early. The parking is free, but limited to only a few cars at a time.
Learn more here.