A Guide to Massachusetts’s Picturesque North Shore Beach Towns

The seaside town that got its own Hollywood drama is a lot dreamier in real life for its beaches and boat moorings.

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Manchester-by-the-Sea

How to get there: Take the Rockport branch of the commuter rail directly from North Station to Manchester. The station sits in the village center, within walking distance of its shops, restaurants, harbor, and Singing Beach.

Keep going north past Salem and Beverly and you’ll hit Manchester-by-the-Sea, a harbor town so picture-perfect it could be a postcard. The compact downtown can be crossed in a matter of minutes, with a short row of shops, a bakery worth the wait, and a train station that still carries commuters into Boston. While the downtown’s worth a visit on its own, most visitors shuffle in for a visit to Singing Beach, a stretch of fine sand just 10 minutes on foot from the train station. Nonresident walk-ons are welcome, though it is worth checking the latest admission and parking rules before you commit to the walk, because the rules shift by season.

Once you’ve had your fill of sand, head back towards Masconomo Park and Tuck’s Point, where you’ll see sailboats on moorings, shingled houses and white clapboard, and a dock or two that look like they’ve been photographed for a hundred real estate listings. The best thing about Manchester-by-the-Sea is that no plan is required—bring the kids, bring nothing at all, and you’ll still leave feeling like you got a full day’s worth of doing nothing.

Where to eat:

Where to stay:

Manchester’s overnight inventory is notably limited, so booking early—or staying in neighboring Gloucester (see below)—is wise.

The historic fishing town of Gloucester offers whale watches, a walkable town center, and waterfront hotels.

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Gloucester

How to get there: You can reach Gloucester directly by the commuter rail from Boston’s North Station in about an hour and 15 minutes. Driving’s a bit more convenient for travelers who plan to move easily between downtown, the beaches, Annisquam, and other parts of Cape Ann.