Castle-Like Victorian Inn Overlooking Inland Waterways

When checking in at Gloucester, Massachusetts’s Castle Manor Inn, don’t expect to find a staff member standing behind a desk. Instead, you walk into a welcoming reception room with Victorian-style couch and chairs, where owner Laura Baker encourages guests to "come in, sit, have a cup or tea, a glass of champagne." That fits in with what Baker says is the recently renovated 1900s-era inn’s new motto: “Relax and let us spoil you.” Grab a pint at the onsite tavern, or soak up the picturesque views of Gloucester’s inland waterways from the gazebo.

With turrets at every corner of the house, the estate looks more like a castle than many Victorian mansions, but the interior still feels like an intimate bed and breakfast. On the ground floor is Sea Glass at the Castle, which serves breakfast and dinner in wood-paneled dining rooms or outside on the wrap-around deck. Chef Tom Johnson—who has studied culinary arts under James Beard Award–winning chefs—prepares haddock roulade stuffed with fresh crab, pan-seared sea scallops, and other seafood dishes. For breakfast, use a $20 credit at the restaurant to sample peanut-butter-stuffed french toast, maple-glazed biscuits, and other morning dishes.

Castle Manor Inn’s rooms are spread among the main building and two wings of mobile lodge rooms. Most rooms accommodate only two guests, but parties of four can ask for the family suite, or E Wing rooms 13–16. Individually decorated rooms include the Scenic Landing room, where blue floral comforter and a painting of sand dunes create a sea motif.

Gloucester, Massachusetts: Iconic Lighthouses, Humpback Whales, and Artists Colonies

About 35 miles northeast of Boston, the fishing community of Gloucester is home to the country’s oldest working seaport. Gloucester was thrown in the national spotlight after Sebastian Junger authored The Perfect Storm, the true story of an epic storm that hammered the fishing fleet and Cape Ann in 1991. The 2000 film starring George Clooney and Mark Wahlberg was shot on location in Gloucester's picturesque harbors.

Here, you can visit the half-dozen lighthouses that stand over the shoreline, some of which date back to the 1780s. Some believe the Cape Ann Light Station on nearby Thacher Island saved the life of President Woodrow Wilson. The lighthouse’s foghorn blare warned the passenger liner that was returning President Wilson to America after signing the Treaty of Versailles. This section of Massachusetts was also named one of the top 10 places in the world to spot a whale by USA Today. From April to October, several whale-watching tours explore the Stellwagen Bank National Marine Sanctuary in search of breaching humpback whales.

The city also boasts one of American's oldest working artist colonies, Rocky Neck Art Colony. Artists such as Winslow Homer and Edward Hopper once called the waterfront community home. Photographers, painters, and potters continue to practice their craft here today, with several exhibition galleries open to the public.

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