For the 50+ Traveler
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Gloucester, a coastal vacation enclave on Cape Ann, is just a 45-minute drive from Boston. With so many great sites to see along the way, you can take a leisurely road trip of several days to enjoy everything the coast has to offer.

If you love the beach, fresh local seafood, and spectacular scenery, you’ll thoroughly enjoy a trip up the coast of Massachusetts.

The Commons and Public Gardens in downtown Boston.

Boston

Boston is known for the Freedom Trail, the Old North Church, and many other historic sites that could take several days to explore. Walking is the perfect way to see the chic tree-lined streets of the Back Bay and Beacon Hill neighborhoods. Elegant old brownstones, sweet sidewalk cafes, and Boston’s quintessential Irish pubs add to the charm of the area.

The Boston Common and the Public Garden are expansive, centrally located green spaces that are worth your time. A ride on the famous Swan Boats is a peaceful way to view the Public Garden. Don’t forget to stop at the statues based on Robert McCloskey’s beloved Make Way for Ducklings. The statues make a great photo op, since the ducklings are frequently dressed in Boston’s sports jerseys.

Neptune Oyster, located in the popular Seaport District, is a must-stop for the seafood lover. You’ll find fresh local catches cooked to perfection. Traditional Italian fare is the name of the game in the North End, where pasta is king and the desserts are decadent. Visit Mike’s Pastry for a delectable Italian pastry to cap off your evening. Boston’s South End is a mecca for hipsters and local artists. Dine at Toro to experience some amazing Spanish tapas.

Plan to stop at Trillium, the brewery rated third in the world by RateBeer in 2019. Boston is famous for its taprooms and breweries. This piece highlights some of the area’s best.

For more on what Boston has to offer, see this page.

Marblehead harbor in Massachusetts.

Marblehead

With deep roots in the fishing industry, the town of Marblehead was once one of the greatest fishing towns in New England. Many townies are still involved in the fishing and lobstering trades, but yachting and yacht racing in Marblehead’s magnificent harbor are also thriving. With access to the open water from a protected harbor, many East Coast boaters make their home in Marblehead.

Marblehead is a great spot to stretch your legs, wander the gorgeous mansion-lined streets, and enjoy the spectacular harbor views of the Atlantic Ocean. Feel your cares melt away as you breathe in the salty ocean air.

Salme Witch Museum in Massachusetts.

Salem

Salem has always been associated with the darker elements of New England’s Puritan past. The infamous Salem witch trials might have taken place way back in 1692, but tourists still come to the town to learn more about that chapter of Massachusetts history.

The Salem Witch Museum takes visitors back to the time of the trials. The 13 life-size stages function as a timeline of events. You will be shocked at how the proceedings were manipulated by the townsfolk.

Salem is a fun place to stroll around, popping into and out of shops. People-watching is fascinating here because the town is a mecca for modern-day witches. Those interested in American literary history will enjoy a visit to Nathaniel Hawthorne’s House of the Seven Gables, and architecture buffs will love the self-guided walking tour of the McIntire Historic District.

This piece highlights everything you need to know about this fascinating city if you plan to visit in the days leading up to Halloween. Be sure to make your reservations early, since the city is inundated with witches, warlocks, and other things that go bump in the night all month long

Salem is a good spot for an overnight stay. If you are looking for a true Salem experience, consider staying at The Salem Inn, which consists of three different homes. The Salem Inn offers a boutique bed and breakfast experience right in the middle of the action. The Curwen House is their adults-only venue; you will feel like you’ve been transported to the mid-1800s.

Another reason to stay the night in Salem is the Bewitched After Dark Walking Tour. This not-to-be-missed tour winds through the streets of Salem, where a guide in period attire will lead you through the town’s dark and stormy past. It’s impossible not to feel a shiver down your back as you pass the old graveyard.

The Manchester-By-The-Sea harbor in Massachusetts.

Manchester-By-The-Sea

Manchester-by-the-Sea, the setting of the acclaimed 2016 movie of the same name starring Casey Affleck and Michelle Williams, is the quintessential New England beachside hamlet. A summer playground for Boston’s rich and famous, the town has glorious summer cottages, seaside resorts, and quaint streets. The harbor is speckled with yachts and sailboats, providing a picture-perfect view for visitors.

Take a walk along Singing Beach, named so because the sand “sings” when you walk on it. There is a small parking lot and a per-car fee. There is a walk-on fee for visitors who do not park.

Stop by Holy Cow Ice Cream Cafe for a sweet, frozen pick-me-up. Try an ice cream cookie sandwich -- it’s a must-have vacation treat.

Hammond Castle Museum in Massachusetts.

Hammond Castle Museum

A true castle in the heart of Cape Ann, the Hammond Castle Museum was the home of inventor John Hays Hammond Jr. Perched on the rocky Gloucester shoreline, the formidable structure is furnished with Hammond’s extensive collections.

A sought-after wedding venue, the castle also makes a fascinating road-trip stop. Both docent-guided and self-guided tours are available. In July and August, the castle offers Thursday Night Candlelight Tours, an intimate way to view the gorgeously decorated rooms.

Rockport harbor in Massachusetts.

Rockport

Next you’ll reach Rockport, famous for Motif Number 1, a replica of a traditional New England fishing shack. The Motif is painted by artists and photographed by visitors year-round. Located on Bradley Wharf in the center of Rockport, it is typically surrounded by easels and canvases in various stages of completion.

For a classic New England lobster roll, venture a little outside of town to The Lobster Pool. The little red shack is a favorite with locals and tourists alike. Perched on a rocky outcrop with limited parking, the shack offers traditional coastal dishes. You can stake out a spot on the grass for a quick meal or carry out a picnic lunch for the beach.

Skyline of Gloucester, Massachusetts.

Gloucester

Gloucester is a hardworking fishing town and the location of many luxury homes. The harbor is home to both fish-processing plants like Gorton’s and seaside resorts like the Beauport Hotel. The Beauport offers upscale, beachy rooms with magnificent views of Gloucester Harbor.

Head to Gloucester’s Main Street for boutique shopping. Many brick storefront shops with one-of-a-kind wares line this sweet downtown area.

Home to seven beautiful beaches, Gloucester has lots of sun and sand to offer visitors.

One of the many beaches in Gloucester, Massachusetts.

Good Harbor Beach is a top choice for beachgoers, but plan on arriving early to secure a parking spot. Parking fees cost upward of $30, but the reward is a gorgeous white-sand beach with restrooms, a concession stand, and wheelchair availability. If you are there at low tide, take a walk out to Salt Island, but be sure to get back before the tide comes in, or you will have quite the swim.

Niles Beach is a lovely stretch of sand where, on a clear day, you can view the Boston skyline. During the summer, resident stickers are required to park, but off-season, it is a nice spot for a quiet picnic.

Wingaersheek Beach sits on Ipswich Bay and the Annisquam River. A concession stand, restrooms, beach wheelchairs, and parking are available. Wingaersheek is a great beach for a day of fun in the sun.

Pavilion Beach is home to Gloucester’s annual Greasy Pole Contest, a raucous, crowd-pleasing event that is part of the Saint Peter’s Fiesta. The festival, held in honor of the Feast of Saint Peter, takes place at the end of June. Traditionally, men from the Italian-American community (though anyone is invited to register and participate) make their way across a 40-foot pole suspended from the pier. Sitting 25 feet above the water, the pole is greased and crowned at the end with the Italian flag. The participants attempt to cross the pole and collect the flag before splashing into the ocean. The test was originally designed to highlight the athletic prowess of the local fishermen.

The road trip from Boston to Gloucester can take an hour or several days. Enjoy the slow coastal drive, take in the beautiful vistas, stroll the quaint New England fishing villages, and let the ocean rejuvenate your spirit.

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