Historic Essex Village | The Perfect Small Town

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Surrounded on three sides by water, historic Essex Village – 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.

All roads lead to the town dock…

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.

Entrance to the museum, with the river beyond

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 #1 on its list of “The 100 Best Small Towns in America.”

Ooh, what a pretty Main Street…

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

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.

The inn’s historic Tap Room

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

And if you’re looking for somewhere to roost, this beauty on Main Street is currently offered by Sotheby’s. Check out the birdhouse.

Further down Main Street: Historic birdhouse for sale, house included…

Post holiday, these Main Street pups still look pretty jaunty.

Post holiday, these pups still look jolly…

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 The French Hen, Toys Ahoy, and The Christmas Barn. 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)

It doesn’t always end well…

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

Peaceful views invite frequent detours off Main Street…

…with frequent detours to the water

…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 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 Museum hosts such singular events as the wildly popular Holiday Train Show, a massive, 26-foot model train layout created by Steve Cryan, now in its 20th year.

Steve Cryan lands a helicopter!

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…

…and in the larger, lovely landscape of a harbor village steeped in history.

…and a final look across the water

  • We are lucky to live here. We pick up after our dogs :). If you haven’t been to Essex, stop in anytime, you will be welcomed.

  • It looks like a great place to live. How do I find out about available homes there or at least BB’s to. Visit?

  • Maggie

    I use to live in Ivoryton and Centerbrook which are in the town of Essex. One of my favorite things to do was walk all over town and see the beauty. My morning walks were the best when the birds are singing and everything is so peaceful. I still miss my walks. Truly a beautiful little town.

  • Ginny,
    we do the Explore New England blogs just for this reason. I hope you take a look at all the ones we have done in the past, and will do in the future.

  • I am collecting places to see in New England ….and this just made that bucket list!

  • Oh, wow…such beauty in these photos and in the words that take us by the hand through this lovely town!! Thank you for letting us know about this pretty little village, which is now on my to-see list!!! :-}


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