Day-trippin’
Exploring the lower Connecticut River Valley
TThe Connecticut River is the longest in New England, flowing from its source in Canada over 400 miles south to Long Island Sound. As it nears the end of its journey, it passes some of the loveliest towns in our state. Every day, thousands of commuters and tourists rush past on the highway, unaware of the natural beauty and rich history of this area. But if you take the scenic route, following the roads parallel to the river, you’ll find innumerable opportunities to stop and experience the charms of one of the prettiest parts of Connecticut.
Seventeen towns comprise the region known as the Lower Connecticut River Valley, and each of them boasts enough attractions and activities to occupy you for hours or days. The following day trip features a selection of highlights, including both established favorites and lesser-known finds. It may tempt you to explore further and make your own discoveries; in this captivating place, it’s hard to go wrong.
Start in Old Saybrook, where the river meets the Sound. This small coastal town has a lot to recommend it, but like its neighbors in the Valley, much of its allure has to do with what it doesn’t have. Because the Connecticut is the largest river in the country without a port at its mouth - shoals and sandbars here make that impossible - the settlements along its banks never developed like those beside other major rivers. So while this was once a prosperous trading and shipbuilding region, in many respects the towns have retained their old-fashioned character.
Before exploring Old Saybrook Center, stop at cozy Ashlawn Farm Coffee (455 Boston Post Road) to grab a warm beverage. Then walk or drive along Route 154, where independent shops and historic homes line an attractive, wide main street.
If you follow this road as it curves towards the water at Saybrook Point, you’ll find Fort Saybrook Monument Park. This was the location of the first Colonial fortification in New England, built in 1636. The fort is long gone, but there is a statue of Lion Gardiner, the English military engineer who built and commanded it, as well as markers explaining the history of the fort and another local curiosity – the Connecticut Valley Railroad Roundhouse and Turntable Site. Here, you can see remains of the 1871 railroad facility, and imagine the days when you could catch a train from here to Hartford. Nearby, an elevated boardwalk winds through a swath of tidal marsh.
At Saybrook Point, Route 154 becomes a causeway leading to Fenwick. Still associated with its most famous historic resident, Katherine Hepburn - and her
family’s dramatic tale of survival during the Great 1938 Hurricane - this small borough is also still renowned for its exclusive atmosphere and sprawling beach houses. The causeway is pedestrian-friendly, so you might want to take a walk along it over picturesque South Cove before retrieving your car and driving to one of Old Saybrook’s beaches.
Harvey’s Beach and Old Saybrook Town Beach (Plum Bank Road) are both small and tranquil, and either is an appropriately scenic spot to say goodbye to the coast before following the river north.
Take Route 154 North to the town of Essex, which consists of three distinct villages. The biggest and most cohesive of these is Essex. At the foot of Main Street, you’ll find the tranquil town dock and the Connecticut River Museum (67 Main St.), which uses artifacts and artworks to tell the stories of the river and the people of this region. Docked beside the museum, you might spot a striking replica of the Onrust, the small ship Dutch explorer Adriaen Block built and sailed up the Connecticut in 1614.
Stroll along Main Street and its short side streets to see why Essex is often called one of the best small towns in America. Make sure to read the historic plaques; much has happened in this seemingly placid village, from the construction and 1776 launching of the Oliver Cromwell, the largest warship in the Connecticut Navy, to the 1814 British raid that resulted in the burning of Essex’s ships and the greatest loss to American shipping during the whole of the War of 1812. ( The latter event is still “celebrated” here in an annual parade.) All around this compact town center, iconic New England sights like the town green,
complete with gazebo, and the photogenic 1776 Griswold Inn (36 Main St.) add to Essex’s timeless appeal. Browse a few of the unique shops and stock up on provisions at one of the local eateries, like quirky Olive Oyl’s (6 Main St.) for a socially distant picnic later.
Continue north up Route 154 to Centerbrook, a low-key village with historic homes, churches, and a tiny town green of its own. Then turn on Main Street (Route 602) and travel a few minutes west to Ivoryton. Named for the imported ivory that manufacturer Comstock, Cheney & Co. once turned into piano keys and profit, this former company town is now better known as the home of the Ivoryton Playhouse (103 Main St.). But even if you’re not seeing a show, the Ivoryton Historic District, encompassing most of Main Street, is worth a quick look. The Playhouse was originally a factory meeting hall, and many of the other, predominantly Victorian, buildings in the village also had their origins in Ivoryton’s mid-19th century company town days.
Back on 154 North, continue to the center of Deep River. Though less touristy than Essex, Deep River offers a vintage Connecticut atmosphere of its own. In Deep River Center, small boutiques and restaurants are wedged beside repurposed industrial buildings, where companies like Pratt, Read & Co. were responsible, along with Ivoryton’s factories, for almost 90% of the country’s ivory production. Complexes like the attractive brick Piano Works building, now converted into condos, turned out not just keys but hair combs and other everyday items. Today, Deep River residents use the town’s history to educate the public about the harms of the ivory trade; the diminutive elephant statue beside the distinctive Town Hall building (174 Main St.) is a part of this effort.
Not far from the center of town, Deep River Landing (River Street and Kirtland Street) provides a peaceful waterside respite. This town was once dubbed “the Queen of the Valley,” thanks to the great wealth the ivory industry brought here, but it might just as well have been a reference to the majesty of views like this.
Keep heading north on 154, then turn left on Main Street to reach Chester.
The adorable and compact Chester Center is known for high quality restaurants and distinctive shops. If you want to get some quick takeout - or a little souvenir - a good bet is Simon’s Marketplace (17 Main St.). The town is also noticeably artistic, boasting multiple galleries and a setting that could be the subject of a painting in itself, with pretty Pattaconk Brook flowing through downtown, and eye-catching buildings on narrow, curving roads. Wander on your own or follow the color-coded sidewalk images of the town’s fuzzy mascot on one of the Chester Historical Society’s self-guided “Chasing Squirrels’’ tours. (Routes can be found at chesterhistoricalsociety.org.)
But Chester wasn’t founded as a cute weekend destination. This, too, was once a mill town, and some of its history can be gleaned at the 19th-century mill site that is now the Chester Museum at the Mill (9 West Main St.).
Another local must is the Chester-Hadlyme Ferry, the second oldest continually operating ferry in the nation. The service is seasonal, and sometimes closes due to hazardous conditions on the river. But if it’s running when you visit, don’t miss the chance to take this
very short and very beautiful ride. Just across the Connecticut is Gillette Castle State Park (67 River Road, East Haddam.) Known as the former estate of actor William Gillette, who built the curious castle on the grounds, it’s also a haven of walking trails and stone bridges, in other words, a perfect picnic spot. After visiting the park, take the ferry back across the river to pick up the route. (If the ferry is closed when you make this trip, you can add Gillette Castle to the end of your drive.)
From Chester, continue north on Route 154 as it parallels the river in the town of Haddam.
Haddam, the only town in the state that straddles the Connecticut River, is packed with opportunities for outdoor activity. With more than 50 miles of trails, this is the place to hike, bike, cross-country ski, or simply experience nature. Two popular options are Haddam Meadows State Park (Route 154), a long and narrow riverfront parcel, and Cockaponset State Forest, a sprawling wilderness split into five sections. Other Haddam highlights include the eye-catchingly yellow Thankful Arnold House (14 Hayden Hill Road), with a noted historic garden; and Camp Bethel (124 Camp Bethel Road), a 19-th century Christian camp meeting site whose brightly painted cottages look plucked from a fairy-tale.
And then there’s the distinctive East Haddam Swing Bridge, which carries Route 82 across the Connecticut River. The bridge itself is a sight to see; catch it at just the right time and you’ll experience it swinging open to accommodate a passing vessel. Drive across it, and you’ll see - if you haven’t already - why Wallace Stevens called the Connecticut “the river of rivers.”
The bridge leads to the postcard-perfect downtown of East Haddam, a scene dominated by the magnificent 1876 Goodspeed Opera House (6 Main St.), which perches on the riverbank above a small park. This little town center
consists of a few businesses and an impressive collection of historic homes. Walk up the hill to see the Nathan Hale Schoolhouse (29 Main St.), one of two one-room schools where Connecticut’s State Hero taught before enlisting to serve in the Revolution.
For a different sort of local history, head to the “ghost town” of Johnsonville ( Johnsonville Road.) This former mill village once harnessed the power of the Moodus and Salmon Rivers to earn the nickname “The Twine Capital of America.” In the 1960s, it had a moment as a tourist attraction, stocked with old buildings trucked in from around the state. That venture eventually went the way of twine manufacturing, and today this abandoned “town” offers a glimpse at some unusual historic structures in a setting that’s as creepy as you make it.
If you didn’t take the ferry over to Gillette Castle earlier, you’re now on the right side of the river to drive there. Alternatively, another well-loved state park in East Haddam is Devil’s Hopyard State Park (366 Hopyard Road), featuring miles of hiking trails, a waterfall that’s impressive in any season, and, some say, the hoof-prints Satan himself. Both are ideal places to end your day, whether you hike, rest, or simply contemplate what to do on your next trip, exploring the rest of the Connecticut River Valley.