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With its boat-filled harbor, white church spires, and charming tree-lined downtown that is now ablaze in fiery hues of orange, red, and lemon yellow, Manchester-by-the-Sea epitomizes your classic Norman Rockwell town with its Instagram appeal. In addition to being snug and walkable, it has seven beaches along its coast and five towns hugging its border—Beverly, Essex, Gloucester, Hamilton, and Wenham.

“There is no other place like Manchester-by-the-Sea because this small coastal town is quintessentially as quaint as it gets,” says longtime resident Holly Fabyan, a vice president at the local real estate firm J. Barrett & Company. “In addition to scenic water views, the town has ample conservation land for hiking and biking, fabulous downtown shopping and eating, and all sorts of art festivals, concerts, and annual traditions, such as Easter egg hunts, July 4th and Veterans Day parades, and Santa’s ride through town on a fire truck.”

Originally named Jeffrey’s Creek, the picturesque community that celebrates its 375th anniversary in 2020 first belonged to the Algonquin Indians, who sold it to early settlers drawn to the area’s sheltered harbor, fishing opportunities, and land for planting. In 1645 the town officially changed its name to Manchester and became populated with dozens of merchant sea captains who traded with Europe and the Far East. From the 1820s to the Civil War, Manchester excelled in furniture making, due to the quality of the region’s timber. When the Union Navy blocked civil ports, however, the town’s 160 cabinetmakers all went out of business.
But Manchester still had cool ocean breezes and water views not found in sweltering cities like Boston, Philadelphia, and New York. Soon, wealthy urbanites began building lavish summer “cottages” along the coast. Actor Junius Brutus Booth (the older brother of the man who shot and killed President Lincoln) even built Masconomo House, a 106-room hotel overlooking Singing Beach complete with tennis courts, bowling allies, billiard rooms, and a grand dining room seating 300 guests.
By the early 1900s, celebrities and dignitaries were flocking to Manchester, including President Taft (and later Woodrow Wilson and Theodore Roosevelt), inventor Alexander Graham Bell, and 11 foreign ambassadors, who moved their embassies to Manchester in the summer of 1904. Over the next several decades, Manchester became less of a summer town and more populated with families eager to live year-round on this picturesque part of the North Shore, which was renamed Manchester-by-the-Sea in 1990.
You can fully explore the town in a day. The MBTA Commuter Rail from Boston drops passengers off in the center of town, where you’ll also find plenty of parking should you choose to drive. If you arrive in time for breakfast, head to local favorite Allie’s Beach Street Café on Beach Street, less than a minute by foot from the train station. In addition to power smoothies and creative lattes with flavors like orange-chocolate, the airy, white-painted eatery serves all sorts of egg dishes, avocado toast, and sweet treats. Once fortified, stroll 20 minutes up to Singing Beach, passing by Manchester Harbor on your right, followed by Masconomo Park, where bands play on summer evenings in the open gazebo. The nearly three-quarter-mile-long beach got its name from the sing-song sound the sand makes when walked upon.

If you have a car, consider visiting Coolidge Reservation, located off Route 127 heading north toward Gloucester. The Trustees of Reservations owns the 66-acre swath of land, which features a great lawn, stunning ocean vistas, woodlands, wetlands, and a beach.
Back in town, grab lunch at Bravo by the Sea, famous for its crispy-crusted wood-fired pizza. In addition to standard toppings like tomato and cheese, they offer toothsome combinations such as sage, pear, and Fontina. Then head to Captain Dusty’s, a local go-to for lip-smacking homemade ice cream in flavors like Dutch chocolate, mint Oreo, and ginger.
With a few exceptions, most stores in Manchester are independently owned, and often by women. A longtime favorite is The Stock Exchange, a 44-year-old consignment shop where you might score a gently used pair of Jimmy Choos, a vintage purse, an Italian linen tablecloth, a chandelier, or even an antique dining room table and chairs. “Our philosophy is to be the destination of choice for discerning shoppers and satisfied consignors,” says owner Lauren Bunker. “The Stock Exchange has an eclectic mix of ever-changing inventory. Customers come to experience the fun shopping atmosphere.”
Mahri is another female-owned boutique, run by award-winning artist and master goldsmith Marianthe Anagnostis Bode. She sells her unique silver and gold jewelry, along with creatively designed women’s clothes, cashmere toppers, hats, handbags, home goods, and other gifts. For eclectic home furnishings, stop by Cargo Unlimited, where you’ll find European furniture, art, lighting, rugs, vintage jewelry, and even some edgy clothes.
Like many North Shore towns, Manchester-by-the-Sea has its fair share of excellent restaurants, such as the recently open Antique Table, serving regional Italian fare like garlicky sautéed clams, pappardelle Bolognese, and panko-crusted local haddock over lemony risotto. The post-and-beam building that houses it was constructed over a century ago and functioned first as a tavern before becoming a stage coach stop, a post office, and finally a restaurant. Another popular hangout is Black Arrow, a farm-to-table eatery owned by Brendan Crocker, who grew up in town. In addition to stellar cocktails, he serves hearty seasonal fare ranging from tuna tartar with crispy wontons to cheeseburgers with homemade fries.
“Generations of families have lived in Manchester and developed lifelong friendships within the community because of its small size,” says Fabyan. “And while very few inhabitants ever leave the town, the ones that do always come back to visit.”

Date of Settlement
1629
Date of Incorporation
1645
Area
18.3  
square miles
Population
5,429
Zip Code
01944
Median Household Income
$105,500