May 6, 2025
By Andrea Valluzzo
Photos by Kim Tyler
Video By Owen Quinn
The picture-perfect town of Essex is an easy get-away from Litchfield and Dutchess counties (about an hour from Litchfield and two hours from Rhinebeck), with an abundance of history, shopping, restaurants, and other attractions. With its quaint Colonial- and Federal-style houses and chic boutiques, it has the classic New England feel of Litchfield, but is also on the Connecticut River and only minutes away from Long Island Sound.
Essex was an important center of shipbuilding and commerce in the 18th century; many buildings bear plaques with the names of the sea captains and builders who were the town’s founders.
Boating is a major draw in summer, when the town’s population swells well over its full-time population of 6,800. Essex is also famous for its parades on Groundhog Day and Halloween, and the Burning of the Ships parade in May that commemorates an 1814 British raid on the town.
11 am
Arrive in Essex Village, park along Main Street, and visit indie shops like The River Lane, a women’s clothing boutique. Owner Robin Zubretsky calls it an easy-to-shop oasis—an atmosphere designed for connections and celebrations among women. “The aim of the store was really to cater to all women and their families. You can shop with your mom and daughter, and they should all be able to find something with the over 50 curated brands that we carry,” she says.
After a morning of shopping, it’s time for lunch and to enjoy the waterfront views. Noah’s at 63 Main has seafood options including seared salmon, crab cakes, or oysters; or the Drift, where a specialty is Old Bay lobster deviled eggs.
Grab a sandwich at Olive Oyl’s Carry Out Cuisine while admiring the vintage petroliana and advertising signs on display. Or visit The Siren Kitchen & Bar, on a small island minutes from downtown. Travel there by boat and dock at the restaurant, or board the complimentary ferry.
3 pm
The Connecticut River Museum has exhibits on the steamboat era, and local industries—from shipbuilding to the famed Dickenson’s Witch Hazel. The British raid in April 1814 is also highlighted; British forces burned nearly 30 privateer ships moored here, and (unforgivably!) took the town’s rum stockpile.
Visitors can climb into a replica of The Turtle, the world’s first operational combat submarine, which was built in nearby Westbrook (there is also a working model, built for the US Bicentennial).
Tribute is also paid to shipbuilder Uriah Hayden, who was selected in 1775 by Connectiut’s governor to build a warship for the American fleet. He built the Oliver Cromwell, across the street from where the museum now stands.
To admire the area’s natural beauty, hop aboard the Essex Steam Train & Riverboat, which offers experiences year ’round. Its dinner trains are popular—especially the murder mystery-themed excursion.
Finish off the afternoon at Essex Mercantile, with everything from apparel and gifts to barware and gourmet foods. Another worthwhile stop: Toys Ahoy!
6 pm
Check in to The Griswold Inn, a blend of sophistication and comfort. With 34 guest rooms, its campus includes the main inn and several historical buildings. Guest rooms are furnished with antiques and fine reproductions; the four-poster beds are from Leonards New England, which has supplied beds to the White House.
The inn is a veritable museum, with a noteworthy collection of art, guns, and maritime artifacts—including a Normal Rockwell sketch of a steamboat race on the Connecticut River. Don’t miss the wine bar’s 18-foot mural of the town, as depicted during the 1880s.
The inn marks its 250th anniversary next June, a month before the nation’s own semiquincentennial. It has remained open through wars, the Great Depression, Prohibition and the COVID pandemic. The Paul family is the sixth to own the inn; they celebrate their 30th anniversary of ownership in October.
The inn offers three dining experiences: one that focuses on New England fare; a tap room with tavern fare; and a wine bar/bistro with small and macro plates, and an extensive wine collection.
After dinner, chill out in the tap room, known for its nightly entertainment.
10 am
Recharge in the morning at the Essex Coffee & Tea Company with a hot or iced drink like toasted almond coffee or a Burundi Kayanza tea. The store-made chocolate coconut macaroons are a must!
Treat yourself to a facial or hot stone massage at the Prive-Swiss MedSpa, or do a bit more shopping.
For a sweet ending to the day, visit Chocolate Geeks, known for artisanal chocolate, including award-winning chocolate ganache shots. Chocolate chip cookies are made in small batches all day, and are both crispy and chewy.
If time allows, catch a show at the Ivoryton Playhouse, which became the country’s first self-supporting summer theater in 1930. Shows this summer include Tea at Five, about actress Katharine Hepburn, who lived nearby in Old Saybrook.
View our Visit to Essex video here!
