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About Town: Deep River

This small town charms with a walkable center, mom-and-pop gems and maritime heritage

  • 4 min to read

In this new monthly feature, we take a closer look a what makes a community in our state a great place to visit or live in.

Talking to people in Deep River, one thing becomes immediately clear: people here really love their town.

“You can live in Deep River and not have a car,” says Hedy Watrous, long-time resident and owner of the downtown breakfast-and-lunch spot Whistle Stop Cafe.

As Watrous and others note, the small town — it had 4,629 people as of the 2010 Census — has a picturesque downtown that is eminently liveable and walkable with a variety of shops, restaurants and essential businesses, including two banks and a classic hardware store, the Deep River Hardware Co. Deep River’s real-world functionality is only the beginning of what attracts people to this Connecticut River town that is bordered by Chester to the north and Essex and Westbrook to the south.

Originally part of the Saybrook Colony, which formally joined Connecticut in 1644, the town incorporated as Saybrook in 1859 and was renamed Deep River in 1947. Initially a shipbuilding and quarrying town, Deep River, along with Essex, became a leading ivory importer between 1840 and 1940 when as much as 90 percent of the world’s ivory was imported by two companies: Pratt, Read & Co. in Deep River and Comstock, Cheney & Co. in Ivoryton, a village in Essex. Primarily used for piano keys, the ivory trade made Deep River a wealthy town, earning it the designation of “the queen of the valley.” Today, the role the ivory trade played in the hunting and killing of elephants is acknowledged with a plaque and statue of an elephant outside Town Hall on Main Street, and the town’s deep connection with its past manifests in historic homes, buildings and a variety of attractions.


Food & drink

If you’re in the area, make sure to spend time in Deep River’s downtown. Here you can eat breakfast or lunch at neighborhood breakfast spots such as Whistle Stop Cafe (108 Main St., 860-526-4122, and Hally Jo’s (65 Main St., 860-526-8838). (People in town rave about the pancakes at Hally Jo’s.) Other options include the Red House (158 Main St., 860-526-2600,, a restaurant with a sleek, red-hued, rock ’n’ roll-inspired decor specializing in American cuisine, craft cocktails and beer. Calamari’s Tavern (75 Bridge St.) is a beloved local dive bar with an old-school vibe that has been owned by various members of the Calamari family since 1933. 


Historic attractions

The site of Deep River’s shipbuilding industry and the spot where ivory arrived in town, Deep River Landing is now a beautiful river park. It is also home to the Becky Thatcher Riverboat and a vintage train station that is a stop on the Essex Steam Train & Riverboat, one of the quintessential Connecticut attractions. Speaking of quintessential Connecticut destinations, Gillette Castle is visible across the river. Held the third Saturday of July, the Deep River Ancient Muster is billed as the oldest and largest gathering of fife and drum enthusiasts in the world. An eye-catching, red-brick building at 150 Main St., the Deep River Public Library was built in 1881 as a private residence. Today, the building’s Queen Anne-style of architecture and rumors of hauntings make it a favorite for visitors. The Grave of XYZ at Fountain Hill Cemetery is a story unto itself. (Read about it in The Connecticut Files on page 120). The Deep River Historical Society is housed in the Stone House at 245 Main St., which dates to 1840. A visit to the historical society provides visitors with more details about Deep River’s compelling connections with the past.



In between eating, you can stroll up and down the main street, taking in some of the historic spots mentioned earlier and checking out storefronts like Alicia Melluzzo Fine Artist & Framer, a gallery and frame shop (124 Main St., 860-539-2529,, or at stylish men’s clothing store Anchor & Compass (163 Main St., 860-322-4327, and its sister store for women, Compass Rose (4 River St., 860-322-4523, Sage Novak, owner of Anchor & Compass and Compass Rose, takes great pride not only in the high-quality items she stocks but in the visually appealing way she presents them. At Anchor & Compass, alongside hats and fine belts, you’ll find books with their covers facing out, which Sage says makes them more eye catching. Sage takes pride in adding human touches to the shopping experience. “I love being part of the fabric of town,” she says.


Living Here

Deep River attracts residents with its combination of on-the-water charm, affordability — the median household income was $69,861 as of 2016, according to the U.S. Census Bureau — and good schools. Because Route 9 runs through town, it is commutable to cities like Middletown (about a 20-minute drive), New Haven (about 35 minutes), Hartford (about 38 minutes) and New London (about 27 minutes). Property owners can also keep a boat at a mooring on the river for no extra cost. 

The Schools

Elementary School: Deep River Elementary School — rating: 7 out of 10

Middle School: John Winthrop Middle School rating: 9 out of 10

High School: Valley Regional High School — rating: 7 out of 10

John Winthrop Middle School and Valley Regional High School are part of Regional School District 4, comprising Chester, Deep River and Essex.

Real Estate

These are examples of homes available for $250,000 to $300,000, according to Mark Reyher, of Reyher Real Estate:

1,900-square-foot Cape • 6 rooms • 4 bedrooms • 2 baths

1,700-square-foot Victorian • 7 rooms • 3 bedrooms • 1½ baths 

3,100-square-foot Colonial • 9 rooms • 4 bedrooms • 2½ baths

Like anywhere else, as you get closer to the water, the price goes up. Currently, options range from:

$475,000 • 2,650-square-foot contemporary • 6 rooms • 3 bedrooms • 2½ baths

$2.175 million • 8,000-square-foot, waterfront Colonial • 11 rooms • 4 bedrooms • 4½ bathrooms • 5 fireplaces • Boat dock

This article appeared in the January 2019 issue of Connecticut Magazine. You can subscribe here, or find the current issue on sale here. Send us your feedback on Facebook @connecticutmagazine or Twitter @connecticutmag, or email

The senior writer at Connecticut Magazine, Erik is the co-author of Penguin Random House’s “The Good Vices” and author of “Buzzed” and “Gillette Castle.” He is also an adjunct professor at WCSU’s MFA Program and Quinnipiac University