March 16, 2021

A Road Trip Getaway North of Boston

Need a weekend away from the city? We’re here to help you plan your road trip getaway with tips on what to see, where to eat and drink, and where to stay!

North of Boston

The North of Boston region begins just 30-miles north of the city. This is a coastal area with historic downtown destinations, beaches, lighthouses, museums, restaurants, breweries, and farmland. Therefore, an insider’s itinerary is helpful to point you in the right direction!  Here’s the scoop on five cities and towns from Boston to our doorstep.

Salem, Massachusetts

First stop, Salem, Massachusetts. This city is known for the fascinating history surrounding the Salem Witch Trials. As a result, witch museums are many! However, there is much more to see and do. For instance, we recommend the world-class art museum, the Peabody Essex Museum. With spacious galleries, impressive architecture, an impressive collection of art. Next, explore the many shops within the pedestrian mall just outside the museum. Finally, a scenic walk to the end of Derby Wharf will lead you past the Salem Maritime National Historic Site which consists of nine acres of land and twelve historic structures along the Salem waterfront.

Cape Ann – Manchester-by-the-Sea, Gloucester, Rockport, and Essex

Next, a visit to Cape Ann. This collection of 4 towns is the perfect destination for a day of seafood, sights, and salty local culture. With rocky coastlines, beaches, iconic lighthouses, art colonies, antiques, and plenty of great places to eat and drink. Therefore, you could easily fill a with stops along roughly 30-miles of the coastal highway from Manchester-by-the-Sea to Essex. Suggested stops on your road trip getaway included:

  • Captain Dusty’s Ice Cream in Manchester-by-the-Sea is a great stop. Park downtown and walk ½ mile up towards Singing Beach, named for the ‘singing’ or whistling sand.
  • Hammond Castle Museum in Gloucester opens seasonally and is known for its striking medieval castle architecture, collection of artifacts, and views of the Atlantic coast.
  • Stage Fort Park and the Fisherman’s Monument on Stacy Boulevard in Gloucester, Massachusetts offer a great place to start while exploring the city.
  • In Rockport, visit Bearskin Neck, home to Motif #1 and over 30 galleries, seafood, and sweet local shops.
  • Halibut Point State Park features a stunning view. You’ll see a quarry filled with water from natural springs that sits just in front of the dramatic rocky coastline. The trails are perfect for hikers of any skill level, with plenty of places to rest along the way. Next, visit The Lobster Pool in Rockport serving lobsters, steamed clams, and homemade chowder. They offer “no-nonsense, no celery lobster rolls”.
    Finally, continue north to Essex where there is a high concentration of fantastic fried clams! With iconic and historic options like Woodman’s of Essex or J.T. Farnhams or newer restaurants like C.K. Pearl or Great Marsh Brewing Company you’ll have great views of the marshland surrounding the Essex River, and the many boats on their way to and from the Atlantic.

Where to Stay: Briar Barn Inn, Rowley Massachusetts

In conclusion, you may need more than just one day to take in the North of Boston region! If you plan to continue exploring north of Boston, our 30-room inn is the perfect place to rest, in Rowley, Massachusetts. Our rooms have a refreshing mix of antiques and artwork, paired with luxury amenities. For example, you’ll find blankets, robes, slippers, a soaking tub, mini-bar, and fireplaces in each room! Dinner at our restaurant, Grove, is a great way to end the day. If you’re with us on the weekend, starting with brunch is the perfect way to fuel up before setting out for the day. We serve brunch on Saturday and Sunday but if you’re with us on another day of the week, try breakfast at the iconic Agawam Diner, a 1950’s era rail car diner with plenty of local roadside charm.

We hope you’ll find this North of Boston road trip getaway guide helpful, keep an eye out for part 2 – with a deep dive into the coastal towns of Ipswich, Newburyport, and Plum Island!