Eastern Point Lighthouse
An active aid to navigation since 1832, Eastern Point Lighthouse marks the entrance to Gloucester Harbor — with the iconic Dog Bar Breakwater offering dramatic ocean views right next door.
Fitz Henry Lane House
Designed by luminist painter Fitz Henry Lane and built in 1848, this granite Gothic Revival home overlooks Gloucester Harbor — offering iconic views that inspired some of America’s greatest marine art.
Annisquam Harbor Lighthouse (Annisquam Light)
One of Gloucester’s oldest lighthouses, the 41-foot brick Annisquam Light has marked the entrance to the Annisquam River since 1801 — best viewed from Wingaersheek Beach across the water.
World War II Memorial
A heartfelt tribute honoring Gloucester’s WWII veterans, merchant seamen, and the families who sacrificed on the home front during one of history’s most defining conflicts.
Dog Bar (at Eastern Point Lighthouse)
Walk Gloucester’s iconic 2,250-foot granite jetty stretching into the Atlantic, with Gloucester Harbor on one side and open ocean on the other — plus stunning views of the Dog Bar Breakwater Light.
Windhover Performing Arts Center
Where the arts come alive under the summer sky — Windhover Performing Arts Center brings world-class dance, theater, and music to a breathtaking Rockport campus each season.
Tuna Hunter Fishing Charters
Head offshore with Tuna Hunter for an unforgettable Gloucester fishing charter — targeting giant bluefin tuna, striped bass, sharks, and more with everything you need on board.
The Trustees of Reservations
From sweeping coastal beaches to historic estates and serene woodland trails, The Trustees steward some of the North Shore’s most treasured landscapes — open for all to explore year-round.
Treetop Yoga
A Cape Ann yoga community rooted in tradition and open to all. Treetop offers expert-led classes, retreats, and outdoor sessions for every level and body.
Stephen LaPierre
Visit Stephen LaPierre’s Harbor Loop studio to watch oil painting in action and explore vibrant plein air works capturing Gloucester, Cape Ann, and coastal scenes from New England and beyond.