Connecticut

Historic Essex, CT | The Perfect Small Town

Surrounded on three sides by water and loaded with small-town charm, historic Essex, CT is a great place to visit in winter.

By Annie Graves

Dec 28 2021

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All roads lead to the Essex town dock.

Photo Credit : Annie Graves
Surrounded on three sides by water, historic Essex Village in Essex, CT – the perfect small town – juts into the Connecticut River like a stubby thumb. A few miles south of here, the river empties into Long Island Sound in Old Saybrook, Connecticut.

Historic Essex, CT | The Perfect Connecticut Small Town

While in Essex, all roads lead to the Town Dock and the adjacent Connecticut River Museum, which was once a historic 1878 warehouse. Today the museum remains a touchstone for the town, hosting exhibits, eagle tours, and special events that draw young and old to its sprawling lawn at the water’s edge.
Historic Essex, CT | The Perfect Small Town
Entrance to the museum, with the river beyond.
Photo Credit : Annie Graves
On Main Street, village shops and early Colonial and Federal-era homes jostle side by side. A short stroll quickly reveals why Essex was named the “Perfect Small American Town” in 1,000 Places to See Before You Die. Another guidebook names Essex, CT #1 on its list of “The 100 Best Small Towns in America.”
A pretty Main Street.
Photo Credit : Annie Graves
Everyone knows the Griswold Inn, fondly known as “The Gris,” which has been welcoming travelers since 1776.
The Griswold Inn has been welcoming travelers since 1776.
Photo Credit : Annie Graves
Could there be a more iconic Tap Room? With live music throughout the week, five dining rooms, historical menus, and a trendy Wine Bar, The Gris plays host to a range of appetites. Folks plan weekends around the inn’s famous Hunt Breakfast on Sunday.
Historic Essex, CT | The Perfect Small Town
The inn’s historic Tap Room.
Photo Credit : Annie Graves
The view across the street from the Griswold Inn seems out of another century.
Across the street, Goods & Curiosities sells gifts with a historic theme.
Photo Credit : Annie Graves
And if you’re looking for somewhere to roost in Essex, CT, this beauty on Main Street was for sale during my visit. Check out the birdhouse.
Historic Essex, CT | The Perfect Small Town
Further down Main Street: Historic birdhouse for sale, house included.
Photo Credit : Annie Graves
Post-holiday, these Main Street pups still look pretty jaunty.
Post-holiday, these pups still look jolly.
Photo Credit : Annie Graves
Up and down Main Street, you’ll find plenty of places to duck in out of the cold. Like the Black Seal, for seafood; Olive Oyl‘s for creative takeout, and Essex Coffee & Tea for pastries and cappuccino. Shoppers can spend their doubloons at shops like The French Hen and Toys Ahoy. Still more temptations open up on North Main Street — Truffle Shots and Weekend Kitchen, oh my.
In fact, there’s a bit of a dog theme (this guy hangs out at Essex Coffee & Tea).
Photo Credit : Annie Graves
The best way to discover this “Perfect Small Town,” is on foot. Sidewalks wind past historic homes snugged up against each other, leading down to the harbor in one direction, or north, out of the village onto wide, tree-lined avenues that spill into parks and conservation land.
Fourteen miles of sidewalks invite strolling.
Photo Credit : Annie Graves
Peaceful views invite frequent detours off Main Street…
Historic Essex, CT | The Perfect Small Town
…with frequent detours to the water.
Photo Credit : Annie Graves
…although it hasn’t always been so quiet. In 1814, the British sneaked up the river and burned 27 ships in Essex harbor. This event, historians say, rallied the Americans to eventually defeat the British during the War of 1812. Each May, Essex, CT remembers it all, in a parade led by fife and drum corps dressed in period clothing, who march through the village streets before winding up at the museum, where hundreds gather for a day of festivities. At other times of the year, the Connecticut River Museum hosts such singular events as the wildly popular Holiday Train Show, a massive, 26-foot model train layout created by Steve Cryan.
Steve Cryan lands a helicopter!
Photo Credit : Annie Graves
Is there such a place as the perfect small town? Essex (which also comprises the villages of Ivoryton and Centerbrook) would say ‘yes there is.’ It’s there in the details…
…pauses to appreciate the details…
Photo Credit : Annie Graves
…and in the larger, lovely landscape of a harbor village steeped in history.
Historic Essex, CT | The Perfect Small Town
…and a final look across the water.
Photo Credit : Annie Graves
Have you ever visited historic Essex Village in Essex, CT? This post was first published in 2013 and has been updated. 

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