Day Trip to Cape Ann
July 31, 2023
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Are you planning a day trip to Cape Ann? Stay at Briar Barn Inn and enjoy the short, scenic drive to the seaside towns of Essex, Manchester-by-the-Sea, Rockport, and Gloucester. Discover sandy beaches, shop boutique stores, explore local trails, experience the arts, and dine at waterfront restaurants with the freshest seafood. Below is a list of our favorite spots throughout Cape Ann.
Essex
Food & Drink
- Woodman’s of Essex – Seafood specialist since 1914 and inventor of the fried clam
- CK Pearl – Fresh seafood with riverside deck seating
- Great Marsh Brewing
- Downriver Ice Cream
Attractions
- Ship Building Museum – A center for education, preservation, and study, of traditional Essex shipbuilding
- Essex River Cruise – Scenic public and private charters

Photo: Expedia
Manchester-by-the-Sea
Food & Drink
Attractions
- Singing Beach
- Coolidge Reservation – “Ocean Lawn” – A scenic pond and a small forest of pine and oak lead you to a spectacular seaside lawn
Rockport
Food & Drink
- Roy Moore Lobster Co. – No-frills seafood eatery & market with outdoor waterfront seating
- Feather & Wedge – Locally sourced menu and craft cocktails
- The Lobster Pool – Outdoor picnic tables on the water serving New England seafood
- The Ice Cream Store
Attractions
- Bearskin Neck & Motif #1 – Downtown shopping, food, galleries, and iconic landmark Motif #1
- Halibut Point State Park – Rock quarry with low coastal shelf overlooking dramatic surf and tide pools
- Shalin Liu Performance Center – Seaside music hall
- Thatcher’s Island & Twin Lights – Lighthouse day trips to Thatchers and Straighsmouth islands.
- Front Beach – Small sandy beach within walking distance to downtown

Photo: Good Morning Gloucester
Gloucester
Food & Drink
- Short & Main – Contemporary bistro featuring creative pizzas and oysters
- Tonno – Italian seafood and old world-style wines
- Minglewood Harborside – Seafood and sushi with deck dining
- Lobasta Land – Local seafood and inventive dishes
Attractions
- Good Harbor Beach
- Wingaersheek Beach
- Schooner Thomas E. Lannon – Set sail out of Gloucester harbor on a 64′ schooner
- Rocky Neck Art Colony
- Hammond Castle
- Maritime Gloucester
- Fisherman’s Statue / Stage Fort Park
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