Things To Do
Castaways Vintage Cafe
Take a stroll downtown and grab a coffee or smoothie at our favorite local café!
Oak to Ember
While Gloucester has no shortage of great restaurants, Oak to Ember is one of our favorites. If you’re in town Friday night, consider enjoying dinner here!
Beauport Hotel Gloucester
A beautiful hotel in downtown Gloucester, the Beauport is a perfect spot to grab dinner or a drink in their cozy lobby on a crisp fall day.
Minglewood Harborside
Best sushi in town!
Gloucester’s Back Shore
If you’re staying at the Ocean House or the Atlantis Inn, the Back Shore is right in your backyard! Enjoy a walk or bike ride along this picturesque oceanfront road.
Gloucester Fisherman's Memorial + Stage Fort Park
Take a scenic walk through town along the boulevard past the famous Gloucester Fisherman statue, then end your stroll at Stage Fort Park for stunning ocean views and the spot where Derek popped the question!
Good Harbor Beach
Even in the Fall, Good Harbor Beach is the perfect place to cozy up on a blanket, watch the waves, or take a relaxing walk on the sand.
Wingaersheek Beach
Wingaersheek Beach is perfect for peaceful walks along the shoreline, enjoying the fall air and views of Ipswich Bay. Katey has fond memories of childhood summers here, and in more recent years Derek has joined her in enjoying beach days here with family and great friends. This is where Katey and Derek took their engagement photos!
Cape Ann Golf Course
For the golfers in the group - grab a tee time and play 9 holes at Cape Ann golf course!
Bravo Pizza
If you're interested in ordering takeout, this is our favorite pizza place in Gloucester, known for its wood-fired pizzas! Order from here and have lunch delivered right to your hotel or Airbnb.