Essex, Connecticut | Could You Live Here?
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.
A hub for festivals, boat cruises, and eagle watches, the Connecticut River Museum, built in 1878, once serviced freight boats along the waterfront.
Credit: Kindra Clineff
A hub for festivals, boat cruises, and eagle watches, the Connecticut River Museum, built in 1878, once serviced freight boats along the waterfront.
Credit: Kindra ClineffCredit: Kindra Clineff 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.

North Cove’s landmark windmill was built as a guesthouse in 1967 and is now for sale ($1.9 million).
Credit: Julie BidwellCredit: Julie Bidwell

Vintage Essex Steam Train cars travel deep into the Connecticut River Valley
Credit: Lori PedrickCredit: Lori Pedrick 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?
THE SETTING
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.
The Black Seal’s pub offers shelter from the storm.
Credit: Julie Bidwell








I DO live here. Have since ’01. A fantastic place to be; wonderful architecture and natural setting, but beyond that, great neighbors and neighborhoods.
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?
Thanks!
Kim
We bought an 1850 house on middle cove (with a river view) for $265,000 4 years ago as a spring to fall retreat. Love it!
I’m looking at Essex as we are considering a move. Are the schools good? Where do folks commute for work? Thanks!