Gloucester, Massachusetts is a charming old fishing town filled with working harbors, rocky coastlines, art galleries, seafood spots and some of New Englands prettiest beaches.

To do:
Explore Rocky Neck, one of America’s oldest art colonies, filled with colorful studios, charming galleries, and dreamy coastal views.
Ice cream at the pink house!
Take the water shuttle ride across the harbor to downtown Gloucester.
Beach day at Good Harbor
Coffee & Shop at Castaways
Watch the sunset on the water
Whale watch with Cape Ann Whale Watch
Live music at Blue Collar

Dine:
51 Rocky Neck- Tucked along Gloucester’s historic Rocky Neck, 51 Rocky Neck is the perfect spot for a beautiful dinner surrounded by art, history, and waterfront charm. The building itself dates back to 1920 and was once an art studio owned by artist Hugh Henry Breckenridge, who studied under Claude Monet.
Seaport Grille- waterfront dining + classic New England seafood
1606 at Beauport Hotel
Blue Collar Lobster- casual & yummy seafood on the water

Shop: Castaway Vintage Coffee Co. for great coffee, smoothies and the cutest beach day accessories and clothing. Alexandra’s bread, The bookstore of Gloucester & The Brass Monkey, for unique gifts and local treasures.

Stay: Luxury townhouse in the heart of downtown by @fodera_management With three bedrooms, three bathrooms, a full kitchen, and a private balcony overlooking the city and water, it was the perfect home base. I loved being able to walk to the harbor, restaurants and shops. Good Harbor Beach is just over a mile away, so you can easily spend the morning by the water and be back downtown for dinner.

Take a day trip to Rockport. Another New England gem to see while you are in the area. Only 15 minutes away from downtown Gloucester.

I grew up coming to Gloucester and it’s always so nostalgic to come back. A place seemingly frozen in time in the best way, add this old fisherman village to your New England bucket list.

xx

Jules