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Essex, Connecticut | Could You Live Here?

Essex, Connecticut | Could You Live Here?
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With a bucolic setting on the Connecticut River and steeped in history and tradition, Essex, Connecticut, was once named the best small town in America.

Essex Village is steeped in history, like a teabag dunked in time. Main Street bristles with homesteads from the early 1800s, architectural gems that draw your eye to the Connecticut River waterfront. Here the British torched 28 ships during the War of 1812, but nowadays mallards rule the docks. The village postman walks 10 miles a day, crisscrossing history, past the 1776 Griswold Inn, and down each twisty lane. Farther down Ferry Street, at the marina, shrink-wrapped boats sit dreaming of tall ships and spring. If you like a parade with roots, you’ll find “all kinds of oddball ones,” one local says. He rattles off Loser’s Day; Trees in the Rigging; and Groundhog Day, featuring a nine-foot fiberglass rodent named “Essex Ed” and families banging pots and pans to roust the sleeping prophet. You can learn a lot about a town by the things that bring it together.

Essex is on the radar, of course. With a population of about 6,500 across three villages, it’s been called “The Perfect Small American Town,” in 1,000 Places to See Before You Die. It’s also top-ranked in The 100 Best Small Towns in America. But those are just numbers. They say nothing about happy dogs cavorting beside their owners by the river, or a “Cultural Hub” that isn’t at all what you’d expect—the kinds of things that matter if you’re trying it on for size, so to speak. Just to see … Does it fit? Do I like it? Could I live here?


First Impression: In-town walking is a breeze (14 miles of sidewalks, depending on whom you ask), and the antique visuals are a history lover’s dream. Plus, it’s an easy amble to the historic waterfront. But almost immediately, I start hearing buzz about the Essex Land Trust, which has championed more hidden walkways than you and your dog can shake a stick at. One of these—Cross Lots—is just across the street from the library. It’s a beauty, with meandering stone walls and gauzy dogwoods, remnants of a 16-acre farm. Fascinating signage reveals the terms of the donor’s will: the farmhouse to be demolished to restore the vista to “a true New England landscape.”

The Reality: Cross Lots is just the tip. The ELT offers hikes, 12 more trails, and kayaking suggestions. If you like your wilderness tamed, pretty Essex Park on Main Street offers benches overlooking Middle Cove, letting you ponder the sailboats flitting by. Kayakers paddle the waters, there’s a choice of yacht clubs, and a schooner plies the river. In February, bald eagles soar to the front, stars of the eagerly anticipated Eagle Watch Boat Tours.


First Impression: Halfway down Novelty Lane, within tossing distance of Middle Cove (if you’re a trebuchet), is the home of my dreams: thimble size, quaintly classic, and equidistant to everything. In the fantasy, I’ve downsized to a few boxes of books, a handful of French antiques, and a small rack of magically versatile clothing. This little dollhouse just might be in my price range. Then I see the ell in back.

The Reality: Less than 10 miles away, Kate Hepburn’s former waterfront estate was previously listed at $16 million. In Essex Village, the average is $665,000—a bargain by comparison. “For under a million, closer to town is better,” says real-estate agent Timothy Boyd. “The closer they are, the smaller the houses get.” Property taxes are low, he adds, “a big attraction for retirees.” Still, Tim quickly locates eight houses for under $300,000 in Ivoryton and Centerbrook (with Essex Village, they make up the town of Essex). Double the $$, and you can move into a sea captain’s house on Bank Lane. “Essex is higher-priced,” he admits. “But real estate on South Cove and the waterfront is very desirable. It moves fast.”

Insider tip: Same school district, but Ivoryton, minutes away, is at least a third cheaper.


First Impression: If you’ve got kids, no problem, affirms Ann Thompson, head of adult services at the Essex Public Library; plenty of Little League and soccer to bond over. Apparently if you have an interest in anything else, too, you’re in luck. The library calls itself “The Cultural Hub”—and it actually is. Currently hosting 348 programs a year, activities include bridge, a knitting club, jewelry making, and lectures ranging from architecture to the paranormal. It’s even got books.

The Reality: If you’re 22, Essex probably isn’t for you. It’s a friendly town, but there aren’t a lot of young singles. “There aren’t many apartments, and no real nightlife,” Ann says. “Town makeup is generally families or retirees,” while younger families gravitate toward Ivoryton. Another route to friendship: volunteering. “Volunteerism is huge,” she says, with a garden club, ELT, Audubon, and, of course, the library.

“I don’t know anyone who isn’t volunteering for something.”

Please Note: This information was accurate at the time of publication. When planning a trip, please confirm details by directly contacting any company or establishment you intend to visit.

Annie Graves


Annie Graves


Annie Graves is a regular contributor to Yankee. A New Hampshire native, she has been a writer and editor for over 25 years, while composing music and writing young adult novels. Find out more about Annie at

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2 Responses to Essex, Connecticut | Could You Live Here?

  1. Jenny Tripp January 8, 2015 at 7:10 pm #

    I DO live here. Have since ’01. A fantastic place to be; wonderful architecture and natural setting, but beyond that, great neighbors and neighborhoods.

    • Kim Romero February 6, 2015 at 2:58 pm #

      Hi Jenny- I was reading this article and didn’t think there would be such a “current” reply!

      My husband and I are thinking about making Essex our next home. We have lived in Westport for 25 years where we raised our twin daughters.

      Can you tell me a little about the variety of people that live in Essex? Why do people tend to relocate there? Interests?

      What do you think of the art, food/restaurants/ boating life of the area?


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