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According to legend, Ipswich’s “Devil’s Footprint” was formed when Satan leaped off a local church steeple. Photo from Historic Ipswich.

Following up on his Ipswich fried clams post — part I of a two-part series on the historic, scenic, and all-around inviting area of Ipswich and Essex, Massachusetts — contributing writer Bob Waite now asks us to back away from the table long enough to enjoy the other sometimes devilish delights the region has to offer.

By Robert Waite

Ipswich, MA – You can have a devil of a time in Ipswich, Massachusetts. Or at least the residents apparently did back in the 1740’s.

According to local legend, a visit by a famous English fire-and-brimstone preacher, the Rev. George Whitfield, to the town’s First Congregational Church, located atop Town Hill, attracted a crowd of thousands – and a curious Satan.

Whitfield, who had no sympathy for the devil, called Satan out. Their raucous confrontation ended with them at the top of the church’s steeple, where Whitfield delivered a denunciation so powerful that it caused the devil to jump…and leave his footprint forever imprinted in the rock below.

Or so the story goes.

Another version of the devil – in the form of Jack Nicholson – visited the town for the making of “The Witches of Eastwick,” the film adaptation of the John Updike novel. Updike, who spent his most productive years as an Ipswich resident, also penned “Couples,” a thinly veiled parable of the joys and pitfalls of small town infidelity. The book ends with a later incarnation of the First Church burning to the ground – as it actually did in 1965.

Fortunately, while there have been six First Church structures on Meetinghouse Green on Town Hill, most of the town’s colonial heritage – and that of nearby Essex – has remained intact.

In contrast to nearby places like Salem and Newburyport, whose deeper harbors facilitated maritime trade (and fueled renewal), Ipswich’s silted river mouth and sand bars left it something of a backwater.

Jack Nicholson as a hungry Devil in the film “Witches of Eastwick,” shot in Ipswich. Photo from Warner Bros.

This Old House

So where others replaced so-called First Period (pre-1725) structures, Ipswichites made do with an occasional fresh coat of paint or the odd addition. The result is that the town boasts more First Period houses than any other community in America.

While most of the houses can only be viewed from the outside, one — the John Whipple House (1677) — is open to the public and well worth a visit. Among other things, note the width of the floor boards, a testament to the old-growth forest encountered by the first settlers.

Led by John Winthrop, Jr., son of the colonial governor, about a dozen men arrived in 1633 and set about building crude dwellings near today’s town wharf as well as a Puritan Meeting House on the same high hill where the sixth version stands today.

If colonial history is your thing, I would highly recommend walking tours offered by a local fellow named Gordon Harris. I took one with my family (pre-COVID) and was amazed by how much I didn’t know about a place where I grew up and worked as a journalist. The tour is not overly strenuous, lasts a couple of hours and typically begins and ends at the Ipswich Public Library.

Another place worth a stop is the Essex Shipbuilding Museum. Essex produced more wooden fishing schooners than any other place between 1668 and the 20th century, and this museum, located in the historic A.D. Story shipyard, offers both exhibits and live demonstrations.

You may recognize Ipswich’s Castle Hill-Great House complex as the location for various films; it also hosts a popular summer concert series. Photo from Trustees of Reservations.

Plumbers Paradise

If your tastes run more to recreation and outdoor activities, Ipswich and Essex offer ample opportunities in stunning settings.

In Ipswich, Crane Beach and its adjacent Castle Hill-Great House complex are the top attractions. The beach and mansion grounds were once owned by the Crane family of Chicago, who made their fortune manufacturing plumbing supplies, including sinks, toilets and the like. Today both are owned and managed by the non-profit Trustees of Reservations.

Crane beach features miles of white sand and dunes and, thanks to one of those sand bars, relatively calm swimming. Calm, but chilly – it typically takes until late August for the water temperature to get much above 70.

Castle Hill and its Great House have formed the backdrop for several films – most notably the aforementioned “Witches of Eastwick” and Greta Gerwig’s “Little Women” (2019) – while the beach was featured in “The Thomas Crown Affair” (1968) starring Steve McQueen and Faye Dunaway. Castle Hill also hosts a popular outdoor summer concert series, which dates back to the 1950’s (and will hopefully return post-COVID).

Although Ipswich today has a population of about 14,000 (and Essex about 3,750), both feel spacious as so much of the land is protected marshlands, beach reservation, or open fields.

Crane Beach is beautiful, but watch out for high parking fees and seasonal greenhead flies. Photo from Trustees of Reservations

Paddlers Paradise

One of the best ways to explore these open vistas is by kayak or canoe. The Ipswich River presents one opportunity – Foote Brothers have been renting canoes on the river for decades and a paddle upriver or down takes you into the tranquility of two state parks and a wildlife sanctuary.

If salt water is more your thing, you can rent a kayak in Essex and paddle down the Essex River to the area behind Crane Beach. In either case, you will be rewarded with natural beauty (and, if you are a birder, a chance to knock a few more species off your life list).

Another way to enjoy the out-of-doors is to visit Appleton Farms. Established in 1638 and maintained by nine generations of the same family, it is one of the oldest continuously operating farms in North America.

The 1,000 acres are now managed by the Trustees of Reservations, and offer access to walking trails as well as farm-fresh goods for sale in their store. The farm still operates in a traditional manner – so watch out for cow pies!

Whether your interests run to history, beach-going, kayaking — or clams — Ipswich and Essex have a lot to offer. But plan ahead – remember, the devil is in the details!


You can find accommodation recommendations in the If You Go section of Part I of this series. If you are interested in a Gordon Harris historic walking tour, he can be contacted via the Historic Ipswich website. There is a modest charge.

Be aware that non-residents are assessed a parking fee of $45 per vehicle at Crane Beach. Also, for about three weeks during the summer (typically late July to early August) the beach and salt marshes are visited by the dreaded greenhead fly. There are no refunds at the beach, so check things out first.

If you are looking for cuisine (other than the fried clams and other seafood covered in Part I), Riverview Pizza in Ipswich is a personal favorite – try the kielbasa pizza, which reflects the establishment’s Polish heritage. For traditional New England fare, Ipswich’s 1640 Hart House is a good choice – my family has gathered there for generations for special events and has yet to be disappointed. Also recommended in Ipswich is Ithaki, which offers a modern and up-scale take on Greek cuisine.

Kayaks can be rented in Essex from Essex River Basin Adventures and both canoes and kayaks can be rented at Foote Brothers, located adjacent to the Ipswich River.

For those interested in my brief inglorious period as a Whipple House guide, you can read all about it here. I still maintain the devil made me do it!

Author Bio:

Robert Waite, who now lives in Ottawa, Canada, grew up in Ipswich, MA, and keeps his U.S. voting residence there. At the age of 12 he dressed in Puritan costume for the town’s annual 17th Century Day, and later was assigned to drive Steve McQueen and Faye Dunaway to and from locations for the film “The Thomas Crown Affair.” He subsequently wrote a column for North Shore Weeklies, a chain of weekly newspapers based in Ipswich, and still writes a weekly column for the local Ipswich paper.

You might also like this recent post by Robert Waite, on travel restrictions at the U.S.-Canada border.

And for another look at Cape Ann travel, see Five Things I Didn’t Know About Gloucester, Massachusetts.


Loved reading this – I was born i Ipswich in 1933 and my sister & I posed in period clothing on 17th Century Day ( we were teenagers ) at the Whipple house and other places around town – have a few pictures as souvenirs. I posted one on Facebook a while back. — Marie Irene (Boudreau) Furbush

Great article. My mom’s a townie and I lived there in the early 70s. I’ve been doing geneaology since ’16 and found she’s descended from the Whipples and Appletons as well as William Story who was the New World patriarch of the line leading to A.B Story — Bret Cantwell

i have an aerial view of that green, showing the church that burned down…i watched it from my window as i lived across the street. Many of the 17th C houses WERE open to the public back when Ipswich celebrated 17th C Day…again, i have many pix of a few of them when we all dressed up…pix of Updike…and girl’s “throwing” pillow lace. Pillow lace was one of Ipswich’s cottage industries. It WAS NOT lace FOR pillows, but rather lace MADE on a rawhide pattern wrapped around a pilow. My house was the middle one on Meetinghouse Green….there used to be another one but it was 1889, the then owners, added a few feet to the house and put on a 3rd floor and a Mansard roof…many of the original thinks were left…a glorious fireplace surroung…indian me if you want pix… — Barbara Stratton-Appleton

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According to government and private surveys:

  • Leading-edge baby boomers (born between 1946 and 1955) and seniors account for four out of every five dollars spent on luxury travel today.
  • Roughly half the consumer spending money in the U.S.--more than $2 trillion--is in the hands of leading-edge baby boomers and seniors.
  • Baby boomers (born 1946-1964) travel more than any other age group.
  • When asked what they would most like to spend their money on, baby boomers answered “travel” more than any other category, including improving their health or finances.

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