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A Day in Essex, Connecticut


About ten miles North of where the Connecticut River empties into the Long Island Sound sits the quiet, sleepy town of Essex. It’s all classic, quaint New England charm: the center of commerce, Main Street, is populated both by historical homes from the 18th and 19th centuries as well as shops, eateries, and the Connecticut River Museum. The residential neighborhoods that frame Main Street are made up of a mixture of mansions and charming cottages. In springtime, the morning air tends toward foggy and smells like old wood, moving water and lilac blossoms. It’s an excellent place to spend the day – here is what we recommend you eat, do, and see while you are there. 


Breakfast: Olive Oyl’s Carry Out. Olive Oyl’s has a delicious selection of breakfast sandwiches. The classic, and most popular, is the bacon, egg, and cheese. It’s warm, delicious, and filling. If the weather is nice, we recommend eating it in nearby Essex Park overlooking Middle Cove.


Carlson’s Landing. These guys do brunch, lunch, and dinner. Seafood lovers, this is the place for you. They are known for their exceptional oysters. The atmosphere can be a bit fancy, so expect linen tablecloths and a mahogany bar.  


Privateer’s Pizza and Provisions. Privateer’s sells groceries as well as thin crust brick oven pizza by the pie or by the slice.  


The Griswold Inn. You can’t visit Essex without at least walking through the Griswold Inn’s dining room – the walls are packed with historical photographs, newspapers, fake windows, tickets, drawings of ships, and more.  


Paddle the Connecticut River Estuary Canoe/Kayak Trail. If you don’t already own a canoe or kayak, there are plenty of places to rent one in the Connecticut River delta. Paddle around Thatchbed Island and Essex Island into Noth Cove around Foxboro Point. 

Take truffle shots. Chocolate Geeks was originally named Truffle Shots after their main product, which are exactly what they sound like: liquid chocolate truffles served in shot glasses. They come in a variety of flavors including sea salt caramel, peanut butter, and fig + balsamic. 

Paint & Sip. Create a beautiful painting with the guidance of talented local artists while you sip from their collection of wine and craft beer. Each class is united around a single painting subject: a lighthouse, a sunset, etc.  


Tree Tour of Essex Park. After you’re done eating breakfast from Olive Oyl’s, perhaps, you can spend a few more minutes enjoying the beauty and serenity of Essex Park. The park is home to several species of tree, and there are signs and placards posted throughout the park to help you identify which type of tree is which.  

The Connecticut River Museum. The Museum is three floors of fascinating maritime history, covering a massive period of time – from the end of the last Ice Age to present day. Explore the history of trade along the river, the construction of the first submarine during the Revolutionary War, the dawn of aquatic motor racing, and more.



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