The Ultimate Day Trip Guide for Bostonians that doesn’t involve the Cape

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Manchester-by-the-Sea is only eight stops on the commuter rail or approximately a forty-five minute drive from Boston, yet when you step off the train platform and into the cozy New England town you cannot help but feel far from anything else in the world.

Manchester was originally bestowed its lyrical nickname to avoid confusion with Manchester, New Hampshire. But since its settlement in 1629, it has moved up the ranks of New England towns from working class fishing haven to Cape Cod’s lesser known, but equally scenic cousin. And thanks to Matt Damon and Casey Affleck, it is now the title of an Academy Award winning film.

From the limited perspective of Summer Street you can pretty much see the entirety of the downtown area. Shops, cafes, boutiques, and mom-and-pop restaurants line the curved streets, only adding to the quaint quality and charm this town has to offer.

Less than a half a mile walk from the center of town is Singing Beach. This picturesque waterfront gets its name from the squeaking sound the sand makes when it rubs against your feet.   Your first peek at the breathtaking view will most likely be all you can see, as the cobalt-blue water reaches out to greet your toes. The beach is fairly small, quiet, and mostly inhabited by locals as the early autumn breeze beckons cooler weather. To your left high reaching rocks stretch out into the sea and to your right the beach continues to curve around the coastline. If you time it perfectly, the sand will transform to an iridescent color as the sun sets over the brisk day. And if you decide to visit during the prime of the summer season please know there is a walk on fee for anyone over the age of 12 between the hours of 9am to 5pm. This is while staff is on duty through Labor Day. They accept cash and checks!

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As you’re leaving the beach and heading back towards downtown, you should definitely stop by Manchester Harbor for the mandatory New England photo-op. There are typically ships docked and it’s the perfect quintessential New England moment to capture for the gram. You will look just like a model for L.L. Bean, bonus points for wearing a cable knit sweater! Next to the harbor is Captain Dusty’s Ice Cream. Captain Dusty’s is a New England based ice cream shop chain that is known for their amazing prices, generous portions, and incredible homemade ice-cream and yogurts. The shop is casual and cozy, and once again, reaffirms the small town vibes of Manchester.

The most important stop in Manchester is Manchester-by-the-book. This used and rare book store is lined and filled with books of all genres. The shop expands all the way to the back storage area, with entire rooms dedicated to young adult fiction, memoir, and music history, not to mention the large fiction section that contains finds like a Dorothy Parker for three dollars or signed copies of This is How You Lose Her. Good luck not getting lost on your way out. At this point in the day you will most likely be in need of food, and you’re in luck. Manchester-by-the-book is about a two minute walk from one of Manchester’s most popular restaurants, Cala’s. They offer classics like clam chowder, but their pan seared scallops will change your life.

It’s not in Manchester, but a quick drive up to Gloucester to visit the Hammond Castle Museum is definitely worth the detour and ten dollar admission. Originally constructed in 1929 by John Hays Hammond Jr., the museum is a modern medieval castle full of booby traps, hidden passageways, and eerie suits of armor. Hammond was the inventor of the remote control and held over four-hundred other patents in his lifetime. He took great pleasure in tricking and scaring his houseguests, one of the most memorable examples is the guest room that is covered completely in wallpaper (including the door) so when the door is shut, it is almost impossible to find. The museum also offers amazing views of the coast, a lovely garden, and a drawbridge (once again do it for the gram!)

On the days where Boston becomes trite or you’re just craving a taste of the slower, simpler life of a classic New England town, Manchester-by-the-Sea has everything you could possibly need. It has the views, the food, and plenty of sites that all fit in its eighteen square miles while still offering the down home vibes you’ve been needing.

Photography by: Jessica Munroe

Rebekah Scarborough