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Trip List by tannerduke

Perfect Day on Massachusetts' Cape Ann

7 Apr 2006  Cape Ann resident for ten years
3.0 of 5 bubbles based on 5 votes

Explore New England seaside towns north of Boston on Cape Ann.

  • Explore locations featured in this Trip List: Gloucester, Rockport, Essex
  • Category: Perfect day
  • Appeals to: Couples/romantics, Honeymooners, Singles, Families with small children, Families with teenagers, Large groups, Seniors, Students, Budget travellers , Active/adventure, Tourists
  • Seasons: Spring, Summer, Fall
  • 1. Start your day in Gloucester
    Gloucester, Cape Ann

    This quaint seaside town is proud of its Italian and Portuguese heritage as well as its fisherman roots. There are numerous galleries and shops along Main Street, parallel to the harbor.

  • 2. Lunch

    For a real Gloucester lunch, go to Virgilio's shop at the end of main street. This Italian staple serves not just sandwiches and pizzas but also a whole lot of character and historical charm.

  • 3. Beach
    Good Harbor Beach, Gloucester, Cape Ann

    Head over to Good Harbor, located just two miles from the town's center, for fine sand and great views of the picturesque coastline.

  • 4. Rockport
    Rockport, Cape Ann

    Historic seaside town with plenty of shops, galleries and restaurants. For a scenic walk, head over to the Halibut Point State Park, about 2 miles North of the town center.

  • 5. Original New England Seafood Dinner
    Woodman's, Essex, Cape Ann

    Located in the seaside town of Essex, you can delight in the traditional seafood fare of New England at the spot where the fried clam was invented. Great spot for families.

  • 6. Cool Jazz Café in Gloucester
    Franklin Cafe Cape Ann, Gloucester, Cape Ann

    If you're looking for relaxed evening entertainment, the Franklin is the place. Stylish, dimly lit establishment on Main Street, serving haute cuisine and smooth Jazz.

  • 7. White Rainbow

    Still not ready to retire? Head across the street to the White Rainbow Restaurant for delicious Martinis.