There are some places that just scream “classic New England,” and Gloucester is definitely one of them. Full of amazing spots to eat, shop and explore, this town is the perfect mix of history and modern excitement. Read on to learn more about why this coastal community should be your next weekend road trip destination.

Just a quick scenic train or car ride north of Boston, Gloucester is America’s oldest seaport.
Flickr/MOTT
Pictured above, Annisquam Light has been guiding sailors home for over 200 years. Today, it's a great spot for a few scenic shots.
Its beautiful beaches, hemlock forests and green parks have inspired artists for generations – its the oldest working art colony on the continent.
Flickr/mgstanton
Check out the Cape Ann Museum for a taste of the rich artistic history of coastal New England. The exhibits are full of work by local artists, past and present.
You'll want to start your visit to this seaport at the harbor.
Flickr/MOTT & Kindra Clineff
Take in the sights, sounds and smells of this historic working seaport. While you're at it, pick up a few of the freshest fish you'll find anywhere.
If all that fresh air and strolling activates your appetite, check out Seaport Grille for delicious and generous portions of lobster fare.
TripAdvisor/Seaport Grille
The restaurant has a large, free parking lot, so you don't need to worry about finding street parking or feeding a meter.
The view isn't too shabby, either.
TripAdvisor/Kevin M.
Grab a table on their patio for the best harborside experience.
One of the most iconic spots in Gloucester is the Fishermen's Memorial on Cape Ann. It bears the names of fishermen who died at sea dating back to the 1700s.
Flickr/amcnair
The memorial was featured in the film "The Perfect Storm."

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Over 10,000 men have been lost to the sea over Gloucester's 350-year history.
Flickr/Karl Kaufman
For comparison, the current population of Gloucester is around 28,700 people.
Wandering the rocky shallows of the coastal areas away from the main drag is a lovely way to spend a late afternoon.
Flickr/Nicholas Erwin
For a more traditional time in the sun, head to Good Harbor Beach. It's a sheltered and gorgeous expanse of white sand and lovely views.
When you need a break from the harbor, go ahead and stop by beautiful Hammond Castle.
Flickr/Eric Kilby
This 1920s stone palace was constructed overlooking the water and features countless rooms full of Medieval, Roman and Renaissance artifacts.
If you decide to spend the night in Gloucester, catch a sunset at beautiful Niles Beach to wrap up your day.
Flickr/Eric Anderson
On clear nights, you can just make out the Boston skyline on the left side of the horizon.
On your way back down from Gloucester, make a detour to Manchester-by-the-Sea and check out the Coolidge Reservation.
Flickr/Ben Saren
Shady trails, quiet glens and the sound of chirping birds will make you feel a million miles away from civilization.
It's a great place to get a taste of the region as it was hundreds of years ago.
Flickr/Ben Saren
And if you start to miss the sound of crashing waves, the reservation has some beautiful coastal spots to spread a blanket or go for a dip.
You can't really escape the ocean in Gloucester, and that's a good thing.
Flickr/MOTT

If you’re looking for an inland Massachusetts adventure, check out this picturesque town that absolutely oozes charm.

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