Travel Guide to Essex, CT, and Its 5 Best Attractions

Step back in time to this historic shipbuilding own.

Hopper Editors - Oct. 26, 2017

Essex, Connecticut, may be the most truly New England town in all of New England. As an early shipping and shipbuilding town, Essex played a key role in the war of 1812, suffering the Great Attack from the British coming in through the Connecticut River. Since then, the town has retained its great American pride, as well as its small-town friendliness. Its streets are lined with historic buildings and houses built in Federal-style architecture – distinctly all-American, dating back to the birth of America. Made up of three very small villages, Essex is a great town to escape to for a few days, to catch a breath of fresh air and walk around in one of the birthplaces of America. Even better, Essex is only a two-hour drive from New York City.

Take a ride through time on the Essex Steam Train and Riverboat

Photo by Gerry Teal via Flickr

The best thing about natural life is that it invariably remains the same over the course of hundreds of years. Peering out the window of the Essex Steam Train on a track that dates from the late 1800s and watching the Connecticut River Valley slowly pass, it won’t feel like much has changed over the past century and a half. This is why this particular attraction is as popular as it is – because it feels like a time machine, and for all intents and purposes, it may as well be one. Take the steam train and riverboat tour and feel the generations evaporate away into the steam.

Go back to school at Hill's Academy Museum

Photo via their official FB page

Built in 1832, Hill’s Academy began as a school for local children, then a boarding house, then a lodge for the Improved Order of Red Men. Now, in its third incarnation as home to the Essex Historical Society, this simple two-story Greek Revival building serves as a meeting place as well as a museum. Visitors curious about the history of Essex would benefit from a wander on the second floor, where they store the artifacts, photographs and archival records of the town.

Catch a glimpse of old Hollywood glamour at the Ivoryton Playhouse

Photo by WCities via Flickr

The building itself was built in 1911, but it didn’t truly come to life until 1930. Milton Stiefel, a traveling director and stage manager, stumbled across an old unused recreation hall in the late ’20s and opened the Ivoryton Playhouse in 1930, making it the first self-supporting summer theater in the United States. Since then, the stage has been graced by Hollywood legends such as Katharine Hepburn, Veronica Lake, Groucho Marx and Marlon Brando. The playhouse is located just a few minutes outside of Essex in nearby Ivoryton.

Taste the sea at the Black Seal Seafood Grille

Black Seal is the epitome of a classic small-town pub – it’s warm, inviting, dimly lit with nautical-themed décor, and it serves up an impressive number of burgers, grilled fish, sandwiches and other classic pub fare. Located in the historical village, the Black Seal is close to the Essex Green, art galleries, and local boutiques.

Rest your head at the Griswold Inn, the oldest inn in the United States

Built in the late 18th century in the midst of the Independence, the Griswold Inn is the oldest continuously operating inn in the United States. Visitors will find a truly authentic maritime lodging experience untainted by the passage of time – the sea shanties sung in the dining room are just as boisterously loud as always, the liquor still flows by the barrel at the Tap Room and the staff are just as welcoming as the brothers who first founded the Gris’.

Photo by Tom Henthorn via Flickr

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