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    7 Activities

    Coastal Cape Ann: Road Trip to the North Shore of Massachusetts

    Coastal Cape Ann: Road Trip to the North Shore of Massachusetts
    Starts from

    Boston

    Transportation

    By Car

    Guidance

    Self-Guided

    Activities

    7

    Duration

    12 hours

    Length

    54 mi

    Guide details

    Starts from

    Boston

    Transportation

    By Car

    Guidance

    Self-Guided

    Duration

    12 hours

    Length

    54 mi

    Natural Attractions
    Map preview

    Created By:

    Kelsey Perrett

    Kelsey Perrett

    Travel Expert

    Highlights

    • Embark on a whale watch from Gloucester Harbor.
    • Photograph (or paint, or draw) the beloved scenery at the Motif Number 1.
    • Dig your toes into the plush white sand of Crane Beach.
    Escape the city to breathtaking North Shore. Aside from the lovely waterfront views and charming coastal towns, you’ll have the chance to delve into the tumultuous history of the Salem witch trials and perhaps catch a glimpse of a breaching humpback whale. You’ll be hard-pressed to find a route more scenic than the Essex Coastal Scenic Byway between Gloucester and Newburyport in Massachusetts. This road trip visits the traditional lands of the Agawam, Wabanaki, Pawtucket, Massa-adchu-es-et, and Naumkeag peoples.
    Please note: It's recommended going in summer for the best beach and whale-watching conditions. Please be aware that certain events may necessitate advance reservations, and event schedules may vary depending on the day of the week and time of year.

    Categories

    Escape the city to breathtaking North Shore. Aside from the lovely waterfront views and charming coastal towns, you’ll have the chance to delve into the tumultuous history of the Salem witch trials and perhaps catch a glimpse of a breaching humpback whale. You’ll be hard-pressed to find a route more scenic than the Essex Coastal Scenic Byway between Gloucester and Newburyport in Massachusetts. This road trip visits the traditional lands of the Agawam, Wabanaki, Pawtucket, Massa-adchu-es-et, and Naumkeag peoples.
    Please note: It's recommended going in summer for the best beach and whale-watching conditions. Please be aware that certain events may necessitate advance reservations, and event schedules may vary depending on the day of the week and time of year.
    Kelsey Perrett

    Kelsey Perrett

    Travel Expert

    • Embark on a whale watch from Gloucester Harbor.
    • Photograph (or paint, or draw) the beloved scenery at the Motif Number 1.
    • Dig your toes into the plush white sand of Crane Beach.

    Day Itinerary

    7 Activities
    Map preview

    Day 1

    54 mi0.2 mi

    Coastal Towns and Whale Watching

    On this exciting day trip, you'll drive along the Essex Coastal Scenic Byway and have the opportunity to explore some of the charming coastal towns of Massachusetts' North Shore. Your adventure will begin in Salem, Massachusetts, where you can visit the famous witch museum and learn about the tragic events of the 1692 witch trials. Next, you'll visit Gloucester, Massachusetts, for a thrilling whale watching tour.
    Then, in the picturesque town of Rockport, Massachusetts, you'll see the iconic red fishing shack that has become a symbol of New England maritime life. In Ipswich, Massachusetts, you can enjoy the stunning beauty of the beach.
    09:3010 min

    Parking Lot

    Parking
    Open Details
    Use this parking lot to visit the Witch Museum in Salem, Massachusetts. The lot is conveniently located just a short walk from the museum.
    0.2 mi5 min
    Salem Witch Museum
    09:451 hr 30 min

    Salem Witch Museum

    Museum
    Open Details
    The city of Salem, Massachusetts, has embraced its witchy history in all sorts of creative ways, so it’s not surprising to find a museum dedicated to the 1692 witch trials in which 20 people were executed and over 200 were accused of witchcraft. This museum is almost as bizarre as its subject matter, with life-sized dioramas and dramatic narrations, but that’s part of the campy appeal. The story spares no detail when it comes to tragedy and execution, so it may not be appropriate for all visitors.
    Tickets are only available online on the day of sale. You must choose a "showtime" for your visit.
    16.6 mi30 min
    Seaport Grille
    11:451 hr

    Seaport Grille

    Seafood Restaurant
    Open Details
    While you're waiting for your whale watching tour, grab lunch at one of the coastal café. Seaport Grille is a favorite for their seafood dishes. The views of the harbor are also breathtaking. The lobster is a must-try, but there are plenty of other fresh seafood options on the menu as well.
    Make sure you keep track of time to avoid missing your whale watching tour; remember to print out your tickets and board 30 minutes before the scheduled departure.
    0.3 mi5 min
    Cape Ann Whale Watch
    12:504 hrs

    Cape Ann Whale Watch

    Travel Agency
    Open Details
    When you visit a place with a rich fishing and maritime history like Gloucester, Massachusetts, it would be a shame not to get out on the water.
    Cape Ann Whale Watch lets visitors do just that with trips across scenic Gloucester Harbor to a location like Stellwagen Bank, where humpback whales are known to breach and spout among the waves. Knowledgeable guides are on hand to answer all of your whale questions, and no matter how much wildlife you see, it’s a great way to get acquainted with the coast.
    It is recommended to arrive one hour before the scheduled sailing time for Cape Ann Whale Watch, as the vessel boards 30 minutes before departure and departs promptly, with no exceptions; visitors also must check in at the ticket office to obtain their boarding pass. This itinerary is designed for a weekends, when whale watching is held at the recommended time. If you are traveling on other days, book the whale viewing in the morning and skip the witch museum.
    4.1 mi15 min
    Motif Number 1
    17:1545 min

    Motif Number 1

    Landmark
    Open Details
    This little red fishing shack on Bradley Wharf in Rockport, Massachusetts, was so oft-painted by a local colony of artists that it came to be known as “Motif Number 1.” It’s easy to see the attraction: the weather-beaten building with its adornments of buoys and stacked lobster traps has a quintessential New England charm.
    Grab dinner or a snack from any of the shops on adorable Bearskin Neck then stay awhile to enjoy the view.
    17.3 mi40 min
    Crane Beach
    18:4545 min

    Crane Beach

    Beach
    Open Details
    While continuing your trip along the Essex Coastal Scenic Byway, you'll be treated to some of the most breathtaking views in New England as you pass through charming coastal towns.
    Crane Beach is lauded as one of the most beautiful stretches of sand in the northeast. This 1,234-acre property, maintained by the Trustees of Reservations, includes miles of Atlantic coastline, walking trails, and the commanding Crane Estate mansion with its Grand Alée rolling toward Ipswich Bay. A couple notes of caution: beach parking gets competitive during the summer months, and dogs are prohibited in order to protect nesting shorebirds.
    16 mi40 min
    Jewel In The Crown
    20:151 hr

    Jewel In The Crown

    Indian Restaurant
    Open Details
    Top off your north shore road trip with a visit to the adorable Merrimack River town of Newburyport, Massachusetts. Tourists trend toward the waterfront dining options, but if you’re looking for something different, the Indian cuisine at Jewel in the Crown lives up to its lofty name.
    The space is secreted into a corner off Pleasant Street. The dining area is simple, but the chicken tikka is just the right amount of spicy, and the attentive waitstaff will make you feel like family.
    Map preview
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