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5 Days of Coastal Charm in Rockport Itinerary

Last updated: 2024 Jun 30

Exploring Rockport's Iconic Landmarks

Morning

Start your day with a visit to the iconic Motif No. 1, a famous red fishing shack that is one of the most painted buildings in America. Enjoy the picturesque views and take some photos to capture the beauty of this landmark. Then, head over to Bearskin Neck, a charming area filled with unique shops, galleries, and cafes. Stroll through the narrow streets and soak in the quaint New England atmosphere.

Afternoon

In the afternoon, embark on Gloucester: Scenic Cape Ann & Rockport Self-Driving Tour. This tour will take you through the scenic landscapes of Cape Ann and Rockport, offering stunning coastal views and insights into the area's history and culture. It's a perfect way to explore more of what this beautiful region has to offer.

Evening

For dinner, enjoy fresh seafood at Roy Moore Lobster Co. This local favorite offers delicious lobster rolls and other seafood delights right by the water. After dinner, take a leisurely walk along Front Beach to enjoy the sunset and unwind from your day of exploration.

Bedtime

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Gloucester: Scenic Cape Ann & Rockport Self-Driving Tour
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Artistic Adventures in Rockport

Morning

Begin your second day with a visit to Halibut Point State Park. This beautiful park offers stunning ocean views from its rocky cliffs and trails that wind through wildflower-filled fields. It's an ideal spot for nature lovers and photographers alike.

Afternoon

In the afternoon, immerse yourself in Rockport's vibrant art scene by visiting some local galleries such as The Art Nook Gallery or The Square Circle Gallery. Spend time appreciating various artworks from local artists that capture the essence of coastal life.

Evening

For dinner tonight head over to The Fish Shack Restaurant, known for its classic New England fare including clam chowder and fried clams. Afterward stop by Brother's Brew Coffee Shop for an evening coffee or dessert before heading back to your accommodation.

Bedtime

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Historical Insights & Coastal Relaxation

Morning

Start your third day with a visit to The Paper House Museum – an unusual attraction where everything inside is made entirely out of newspaper! It’s both quirky and fascinating providing insight into creative recycling methods from decades past.

Afternoon

Spend your afternoon at Pebble Beach which is known for its smooth pebbles rather than sand making it unique among beaches in this area; perfect spot for beachcombing or simply relaxing while listening waves crash against shore.

Evening

Dine at Feather & Wedge, an upscale restaurant offering contemporary American cuisine made with locally sourced ingredients; perfect way end another wonderful day exploring all that Rockport has offer.

Bedtime

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Seaside Serenity and Local Flavors

Morning

Begin your day with a peaceful walk along the Rockport Breakwater. This long granite pier offers stunning views of the harbor and is a great spot for some morning reflection or photography. Afterward, head to Bean & Leaf Cafe for a delicious breakfast and some freshly brewed coffee.

Afternoon

In the afternoon, visit the Rockport Art Association & Museum. This historic institution showcases works from local artists and offers a glimpse into the rich artistic heritage of Rockport. Spend some time exploring the various exhibits and perhaps even attend a workshop or demonstration if available.

Evening

For dinner, make your way to My Place by the Sea, a highly-rated restaurant known for its exquisite seafood dishes and romantic oceanfront setting. Enjoy a leisurely meal while taking in the breathtaking views of Sandy Bay.

Bedtime

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Final Day of Coastal Exploration

Morning

Start your final day with a visit to Straitsmouth Island Lighthouse. Although you can't enter the lighthouse itself, you can enjoy beautiful views from afar and learn about its history through informational plaques. It's a serene spot to start your day.

Afternoon

In the afternoon, take part in another tour from your wishlist: Gloucester: Scenic Cape Ann & Rockport Self-Driving Tour. This tour will allow you to revisit some favorite spots or discover new ones as you drive through picturesque landscapes.

Evening

End your trip with dinner at Nate's at Front Beach, where you can savor delicious seafood while enjoying views of Front Beach. After dinner, take one last stroll along Bearskin Neck to soak in the charming atmosphere before heading back home.

Bedtime

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