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Miles of undulating shoreline, a trove of historical homes, and a lively, walkable downtown all make Ipswich an appealing destination in the summer. When the beachgoers head home and the temperature drops, however, the town becomes a different place, ready to reveal unexpected pleasures to visitors willing to take the time to seek them. 

From peaceful views over the marshes in late fall to lush Christmas celebrations, Ipswich in the off-season is worth a visit. “It’s more than just the beach,” says Ray Morley, president of the Ipswich Chamber of Commerce and owner of the Ipswich Inn Bed and Breakfast with his wife, Margaret.

The character of Ipswich is tied to its history. Nestled against the expansive marshes that surround Ipswich Bay, the town was founded in 1633 by settlers drawn to the safe and pleasant harbor the land offered. The nearby deep-water harbors of Newburyport and Salem, however, attracted more commerce, and Ipswich never developed a thriving signature industry. Lace-making and stocking production each had their day, but Ipswich remained primarily a fishing and farming community. 

Bound together by a common cause, early inhabitants of the town developed the self-sufficiency and community spirit that characterize it to this day. Even now, residents often refuse to call their town a suburb of Boston, preferring to identify as an independent community. 

Historians believe that these circumstances also explain the disproportionate number of homes remaining in Ipswich that date to the 17th and early 18th centuries. Residents had little time or money to spend on updating and upgrading their houses, so the historic features survived. 

The town’s spirit emerges in full force during the holiday season, which begins in earnest with Halloween, Morley says. The town closes down a portion of High Street, and hundreds of trick-or-treaters come through.

Photograph by Elise Sinagra

By the time December approaches, the town is decked out and abuzz with Christmas energy. A towering evergreen downtown is strung with lights and hung with stars bearing the names of loved ones residents have lost. Santa Claus arrives by boat and is escorted to the town center by firetrucks and children eager to catch a glimpse of the big guy. Churches hold Christmas bazaars and carol singalongs. 

At Morley’s inn, traditional décor and a towering tree make the common rooms festive. “You come in here and you’re going to smell the tree right away, you’re going to smell pies baking,” the innkeeper says. 

Photograph by Teddy Doggett

Early in December the mansion on Castle Hill at the Crane Estate is decorated for Christmas, kicking off a series of holiday events at the historic home. From December 6 to 8 this year, the estate is presenting An Old-Fashioned Christmas, three days of holiday events in and around the house. Local florists and garden clubs will adorn the house in lush greenery and flowers, and guests can sip cider (or cocktails, depending on the hour), watch dance performances, partake in a treasure hunt, and visit with Santa Claus. “If you’re looking for an event that will immediately put you in the holiday spirit, this is really a good place to come,” says Trina Schell, public events and community outreach manager. “Plus, you can get some great decorating ideas as well.”

On the other side of town, Marini Farm transforms itself from a farmstand into a holiday wonderland. The festivities kick off on December 6 with the unveiling of the Tree Jubilee, a fundraising raffle featuring beautifully decorated trees and wreaths donated by area families, businesses, and organizations. The fun continues through the month with (very popular) wreath-making classes, gingerbread decorating workshops, and hot chocolate buffets. During good weather, you might luck into a hayride or some s’mores next to the outdoor firepit. “It is one of my favorite times of the season,” says owner Michael Marini. “We have time to talk to people and everybody is just so happy that time of the year—it’s such a great family feeling.”

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At Appleton Farms, on the southern edge of town, the season kicks off with a family party celebrating the Scandinavian tradition of the Nisse, a mischievous Christmas elf. The line-up for the rest of the month includes a gingerbread story time, a lantern-lit winter solstice stroll, and a scavenger hunt–style walk to seek out wooden reindeer hidden around the property. 

And even in the chillier weather, Ipswich’s natural beauty is not to be overlooked. If you want to step back from the sometimes chaotic fun of the season, visit Greenwood Farm to surround yourself with the isolated beauty of the marshes, or pause for a moment on the Riverwalk to contemplate the reflections of bare trees and wintry skies in the Ipswich River. Or you can always head out to the end of Argilla Road for a walk on the beach.