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 my favorite ways to spend an afternoon in Gloucester is wandering around Rocky Neck, one of America’s oldest art colonies. There’s something so charming about this little waterfront neighborhood, with colorful studios, tiny galleries, weathered shingled buildings, and boats bobbing in the harbor. Take your time walking around, pop into the galleries, and enjoy the dreamy coastal views. It feels like the kind of place where you could easily lose track of time.

Ice Cream at the Pink House

No summer day in Rocky Neck is complete without stopping for ice cream at the famous pink house. It’s one of those little Cape Ann moments that feels almost too cute to be real. Grab a cone, wander along the water, and take in the colorful surroundings. Of course, you’ll want a photo or two while you’re there.

Take the Water Shuttle to Downtown Gloucester

For a fun way to see more of Gloucester, hop on the water shuttle across the harbor to downtown. I always love when getting from one place to another can be part of the experience, and there’s something especially lovely about seeing the town from the water. It’s a much more charming way to arrive than getting in the car, and you get beautiful views of the harbor along the way.

Spend the Day at Good Harbor Beach

If you’re looking for a classic New England beach day, head to Good Harbor Beach. The long stretch of soft sand and beautiful blue water makes it one of my favorite places to spend a sunny afternoon. Bring a beach bag, something good to read, and plan to stay for a while. It’s the perfect place to slow down and let the day feel a little longer.

Coffee & Shopping at Castaways

For a little coffee break, stop by Castaways and spend some time browsing around afterward. I love finding those small local spots that make a destination feel more personal, and this is a nice place to work into a morning or afternoon of exploring. Grab your coffee, wander around, and see what you find.

Watch the Sunset on the Water

Make sure to leave some time in your itinerary for sunset. There’s something about watching the sun go down over the water in Gloucester that makes you want to put your phone away and just take it all in. Whether you’re out on a boat or simply sitting along the harbor, this is one of those moments I wouldn’t skip.

Go Whale Watching

If you’re visiting Cape Ann in the summer, a whale watching trip is a must. Head out with Cape Ann Whale Watch for the chance to see whales just off the coast. Being out on the open water with the breeze coming through your hair and the possibility of spotting a whale in the distance is such a special New England experience. It’s one of those things you’ll be talking about long after your trip.

Listen to Live Music at Blue Collar

End the day with live music at Blue Collar. After a day spent at the beach, wandering around Rocky Neck, and being out on the water, this is the perfect way to ease into the evening. Grab a drink, listen to some music, and let the night unfold. There’s something about live music by the coast that makes even an ordinary evening feel a little more memorable.

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