Before there was Connecticut, there was the Connecticut River. It begins near the Canadian border and flows for over 400 miles before it meets Long Island Sound at Old Saybrook. It slices the state of Connecticut in two, flowing past major cities, rural towns, bleak industrial areas, and villages whose riverbanks hold on to memories of their shipbuilding and seafaring past. They are all worth exploring, but for an intriguing introduction to the impact and culture the river, this little segment of the Lower Connecticut River Valley is a good place to start.

The trip begins in Essex, where historic meets preppy in a classic New England riverfront setting. It winds north to quieter, humbler Deep River, then continues on to the pocket-sized and intensely charming downtown of Chester.

From there, where you choose to go is up to you – and, of course, what the river suggests.

Essex:

Essex is upscale but not snobby, the sort of place where people wear pink chinos without irony but also genuinely smile and say hello to strangers on the street. Its wealth and waterfront location have made it a target in war: in 1814, British forces raided the town, burning 28 ships in the harbor – worth $200,000, a staggering amount at the time – and stealing over $100,000 worth of rum. Today those assets make Essex an idyllic place to live and a magnet for visitors looking for a classic coastal New England atmosphere. The center of Essex Village is comfortably walkable and easy to navigate.

Start at Olive Oyl’s (6 Main Street) for coffee and breakfast. Offering a mix of baked goods, sandwiches, healthy-ish packaged snacks, and vintage candy, this little spot with indoor and outdoor seating feels like a local favorite that’s been around forever. Don’t miss the collection of vintage signs spread around inside.

One attraction of a stroll down Main Street is that it’s essentially a self-guided tour of elegant historic homes. The other is that it’s lined with shops you won’t find anywhere else. One of my favorites is Goods & Curiosities (47 Main Street), the expansive and surprisingly varied gift shop of the famous Griswold Inn across the street. (That’s where the British stole the rum from.) Stop into the adorable Essex Duck (51 Main Street), which is, yes, an entire (very tiny) shop devoted solely to rubber duckies. Also check out Weekend Kitchen (16 Main Street), which despite its name sells lovely gifts not just for the kitchen or dining table, but every room in the house. Don’t neglect the shops just off Main Street, like Partners Antiques (7 North Main Street), a relaxed and affordable alternative to the higher-end antiques stores in the region.

As you walk along Main, take the time to wander down a few of the small side-streets as well. Soon, you’ll reach the end of the road – where cars have to turn around to avoid launching themselves into the water – where you’ll find the Connecticut River Museum. Perfectly sized for a quick yet rewarding visit, this museum tells stories of life on the river through its collections of paintings, photographs, tools, and other artifacts. Highlights include the Connecticut-made Turtle (the first submarine used in combat), and what might just be my favorite mural in the state.

Walk back on Pratt Street, parallel to Main, for a slightly more of “behind-the-scenes” view of this waterfront community, and more lovely houses.

Tips & More:

The town of Essex is comprised of three villages: Essex Village (the location of all the highlights in this post), Centerbrook, and Ivoryton. If you type “Main Street, Essex” into your GPS, it will send you to Centerbrook and you will be confused. To outwit it, use the Connecticut River Museum or another business address for correct directions.

There are public restrooms hiding in Essex Park on the south side of Main Street.

If you have more time, consider taking a ride on the Essex Steam Train & Riverboat. It’s a local favorite attraction that gives you a perspective of the region you can’t get on foot or in a car, and there are many options for different excursions of various lengths.

Deep River:

Once a major player in the ivory industry and wealthy enough to be called “the Queen of the Valley,” Deep River is now a self-proclaimed “best kept secret” of the region. And whoever came up with that line isn’t wrong. Of the three towns in this post, Deep River hews the closest to its industrial heritage, and has retained a proudly unfancy atmosphere. That’s not to say it doesn’t have many facets to explore. Very few places in Connecticut are truly undiscovered, but this small town still feels like a secret waiting to be shared.

From Essex, drive north on Book Hill Road and Essex Street then turn right on Route 154, which becomes Deep River’s Main Street. Here you’ll find timeless essentials, like the old-school hardware store, as well as a few quirky shops like Celebrations (161 Main Street), a great place to stop if you need a greeting card, and Bennett’s Books (171 Main Street.)

Stop to see the small bronze elephant statue in front of Town Hall (174 Main Street). It is one of many ways residents of Deep River now educate the public about the town’s history while acknowledging the tragic impact its erstwhile glory had on elephants – as well as on enslaved Africans forced to participate in the ivory trade.

Then head to the Whistle Stop Cafe (108 Main Street) for lunch. This old-school corner diner shrunk down to teeny-tiny proportions is best known for its breakfast options, but there’s also a lunch menu of sandwiches, burgers, and more. And despite the small-town greasy spoon atmosphere, much of the food is locally sourced and organic.

Then head to Deep River Landing (River Street and Kirtland Street), less than a mile away. This peaceful public space, with a dock, a gazebo, and a circular wooden deck overlooking the water, is the perfect vantage point to sit and watch the river go by.

Tips & More:

After lunch, take a look at the impressive brick Piano Works building, built in 1914, that’s located on Main Street just past the Whistle Stop. It’s a condo building today, but it was once the headquarters of a company manufacturing ivory combs and piano keys, and it offers a glimpse of Deep River in its former life.

As you park at Deep River Landing, you’ll pass the 1915 Deep River Freight Station. This depot, one of two surviving Connecticut Valley Railroad stations in the region, is listed on the National Register of Historic Places. You may also see the riverboat Becky Thatcher dock here to pick up passengers from the Essex Steam Train.

Chester:

Chester’s hilly topography and its mix of independent shops and acclaimed restaurants gives this town, one of Connecticut’s prettiest, a surprisingly European flavor. Once a mill town with deep ties to the river that runs along its eastern border, it’s now simultaneously rural, artsy, and sophisticated – the perfect place to conclude your short trip or be tempted into continuing up the Connecticut River Valley for more.

From Deep River, continue on Route 154 North then turn left on Route 148 to reach downtown Chester.

Much of the attraction here is the setting itself, with its brightly-accented historic buildings arranged at unusual angles. There’s more to do than simply meander, however. Chester Center is quite small, but it’s packed with art galleries and boutiques like French Hen (4 Main Street), for gifts and housewares, and Perfect Pear (51 Main Street), for practical yet aesthetically pleasing cooking supplies. Simon’s Marketplace is a good place to buy a tasteful little souvenir, as well as to grab a drink or snack. During the summer season, Pattaconk Creamery (33 Main Street) sells ice cream through a window, adding to the sense that Chester just might be a tiny fantasy land, where everyone is on a permanent holiday.

Tips & More:

Chester Center can get crowded, so don’t try to drive from place to place. Instead, find a parking space (if the Main Street spots are full, there’s a large public lot up the hill on Maple Street) and walk around downtown.

Look behind and between buildings for Pattaconk Brook, which flows unobtrusively through downtown and gives Chester some of its old-world, small-scale appeal.

If you have some extra time, or if you’re already heading east towards home or your next destination, skip the bridges and cross the river the way locals have been doing it for hundreds of years: on the Chester-Hadlyme Ferry. The second-oldest continuously operating ferry in the state (the oldest can be found about 25 miles north, running between Glastonbury and Rocky Hill), this tiny car ferry is a classic Connecticut travel experience. On the Hadlyme side, you can stop at Gillette Castle State Park, also reachable from the Essex Steam Train & Riverboat, mentioned above.