Route 44 descends from the rolling hills through a series of switchbacks leading to a hamlet nestled in the valley below. The roadside grasslands — still fawn in color during the first week of April — show peeks of verdant green along the brooks that flow down the hillside. The small village, located at the intersection of two main roads, is framed by farm fields and a golf course.

Amenia is a quaint village nestled in the rolling farmland of Dutchess County, New York. With a population of just over 3,700, it boasts a vibrant Main Street with restaurants, an antique shop, a florist, and other small businesses. The village welcomes visitors from all over, and most visit to enjoy the slow pace and quiet serenity of village life. 

On my first drive down Main Street in Amenia, it struck me that this village is a mirror image of Chepachet, Rhode Island, and Route 44 is the thread that connects the two.

100 Years of American Travel

One hundred years ago, the federal government decided to establish a numbered highway system to accommodate America’s new love affair with the automobile. The sudden freedom to travel anywhere at will brought prosperity to communities large and small throughout the country. For example, Route 66, one of the first numbered highways, allowed people to drive from Chicago to California via a single roadway. 

Route 66 was christened “The Mother Highway” in Steinbeck’s 1939 classic novel, The Grapes of Wrath. Over the years, stories of travel on Route 66 have been seared into our collective memory through popular movies, television shows, and songs — everyone knows the lyrics, “I got my kicks on Route 66” — and the iconic motorway’s 100th anniversary will be celebrated in November 2026.

Route 44 isn’t nearly as famous, but it’s important nonetheless. It was commissioned 9 years later after Route 66 in 1935, and the 273-mile route connected Kerhonkson, New York to Plymouth, Massachusetts. The road passes right through Chepachet, Rhode Island, and many of us in northern RI travel it daily. 

The purpose was to encourage travel from New York’s Hudson River Valley to the shores of the Atlantic Ocean in southern New England. The feat was accomplished by stringing together existing turnpikes, like Putnam Pike, with local connector roads. The effort created a route that brought people through metropolitan areas, small towns, and rural villages.

The Road I Traveled

The goal of my road trip was to see the other end of Route 44 — I wanted to know: what’s beyond Putnam Pike? I picked up Route 44 in New Hartford, a small town west of the Connecticut River. This route avoids the sections of Route 44 that merge onto the interstate highway in Hartford. (Remember, my goal is to avoid interstates on my journeys!) 

Once over the river, I merged onto East Hartland Road — Connecticut Route 216 — heading west out of Granby. It turned out to be a very good decision. The descent into New Hartford following this road was the most memorable part of my drive.

The serpentine curves in the road go on for what seems like an eternity. (In reality, it’s only two miles.) The low, rusted steel guard rail on the edge of the pavement is all that separated my Mercedes from the steep slope down to the wooded shoreline of Lake McDonough. The speed limit of 30 miles per hour is definitely warranted, but with no traffic on the road, every fiber in my body wanted to take the curves at a higher speed, pretending to be part of a car chase in a James Bond movie. A final 90-degree turn over the dam that creates this lake, and I was on the home stretch. Just one mile ahead is my first glimpse of Route 44. 

My destination was still some 50 miles away, which left me with plenty of driving to do along the two-lane road as it snakes around the picturesque Canaan Mountain in northwestern Connecticut.  

Where to Sleep & Eat in Amenia, NY

In Amenia, there are limited options for overnight accommodations. Personally, I’m a fan of small inns and comfortable bed and breakfasts, so for this road trip, I chose the Hilltop House Bed and Breakfast. The house boasts a west-facing wraparound porch that provides guests with sunset views during the summer season, and a portion of the porch is even screened-in for particularly buggy nights. 

There are four comfortable rooms available to guests at this B&B. The common area is spacious and has a large stone fireplace, and quirky antiques decorate the rooms and common areas. Plus, the Wi-Fi signal is strong throughout the house. 

Staying over on a Monday night, I expected to have the house to myself. To my pleasant surprise, a family on an Appalachian Trail hike decided to stay over as well. Our host served a delicious breakfast to all four guests the following morning. The conversation after breakfast lasted over an hour, and new friendships were formed.

The village’s most popular tourist venue is the Four Brothers Drive-In, which includes nighttime films, as well as food, drinks, and even accommodations. The food court has a tiki-bar feel, and visitors have the option to “glamp” in an on-site Airstream camper. The seasonal drive-in is also connected to the Four Brothers Pizza restaurant that is open year round.

In terms of other restaurants, Isabela and Panacea are two popular options in the village proper. Unfortunately, neither was open on that Monday night, which forced me to look outside of Amenia for dinner. 

By chance, I stumbled upon the Blackbird Bistro. This small cafe is located 5 miles outside the village — I initially drove right past the place, not realizing it shares a space with a Mobil gas station.

The Blackbird Bistro has just eight small booths, as well as a five-stool bar, but the number of dinner choices available on the menu is surprising. The night’s special, called “Lollipop, Lollipop, Lollipop,” piqued my interest, and it proved to be a great choice. The lollipop lamb chops were incredibly delicious, and the amount of food on the plate — eight lamb chops, plus roasted potatoes and sautéed vegetables — was impressive to say the least. As for the quality of the food? The only adjective to describe it is “superb.” Without a doubt, this would be a regular date night dinner spot with my wife if I lived in the area.

Things to Do & See

It’s surprising how much there is to experience within 20 miles of the village. Amenia is just three miles west of the Connecticut border, opening up the state’s northwest corner for exploration from this home base. 

Lime Rock Park offers car buffs a full summer season of motorsports. Mohawk Mountain Ski Area has 27 trails for skiing and snowboarding adventures in the winter. My favorite day trip option might be Thorncrest Farm & Milk House Chocolates in Goshen — think Wright’s Dairy Farm, but with milk chocolate made on-site.

Dutchess County is classic northeast farm country. Large and small farm stands dot the surrounding area, and many offer the opportunity to see farm animals. There’s also the Trevor Zoo, a family-oriented experience open year round, in the adjacent town of Millbrook. 

For adults-only getaways, there are several distilleries and vineyards within striking distance of Amenia. Tenmile Distillery and Hillrock Estate Distillery are two local favorites — they each produce single-malt whiskey, along with other spirits like gin and vodka. Another option is Millbrook Vineyards and Winery, which has over 130 acres of red and white grape vines used in the production of its wine. The vineyard produces award-winning Pinot Noir, Cabernet Franc, Chardonnay, and Riesling vintages. It’s open seven days a week, year round, and has extended daily hours during the summer months.

The Road Home

The morning after my stay brought clouds, snow, and sleet! Not the best weather for the road trip home. 

Due to the inclement conditions, I decided to change my route home. Instead of going back on Route 44, I headed east out of Amenia on Connecticut Route 4. This two-lane road snakes through the middle of the hills surrounding Canaan Mountain, and it’s a curvy road with steep grades. The Mercedes actually had a bit of trouble making it up the inclines in several locations, but fortunately, there wasn’t a lot of traffic on Tuesday morning.

The road cuts through the Mohawk State Forest, and there are picnic areas adjacent to a small creek at three locations in the park. If the weather had cooperated, I would have stopped to enjoy the sites and sounds of the mountain and stream.

I passed through the small cities of Stafford Springs, Winsted and Canaan on my drive to Amenia. The road home bypassed the two latter towns, and by early afternoon, the weather cleared enough to stop and stretch my legs in Stafford Springs. 

The main drag in the town is a marvel of 19th century mill town redevelopment. A single railroad track cuts through the downtown along the west side of the Middle River, and the street is lined with benches to sit and enjoy the vibe. Unfortunately, it was late afternoon, which meant Lu Ann’s Bakery and Cafe was closed. However, it’s definitely worth a jaunt back here to check out the place.

It’s Time to Explore Route 44

I have always been curious to find out what lies beyond Putnam Pike in western Connecticut. I’ve traveled from Chepachet to Pomfret, and sometimes beyond, many times, but I have never explored Route 44 as it extends west of the Connecticut River. I can honestly say that the drive from New Hartford to Amenia did not disappoint.

The 50 mile journey is relatively short but provides scenic views of farmland, forests and low mountains throughout the drive, and there are plenty of places to stop and enjoy the peace and serenity of the local environment. The conveniences offered in the towns and small cities along the route also ensure the opportunity for bathroom breaks. 

My choice of Amenia as a final destination was random. I had read an article about the village in the New York Times last fall, and when I looked up the location on a map and noticed Route 44 cut though the center of the village — decision made.

I did not know what to expect when I arrived in Amenia. What I found were shops, businesses and restaurants concentrated along a half mile stretch of Main Street — Route 44. The town hall — a converted school — sits on a small hill overlooking the village. It mirrors the stretch of Putnam Pike in Chepachet that has a restaurant and small businesses concentrated in the center of the village around the Glocester town hall. I felt comfortable and at home as I walked through the village of Amenia.

Now that my curiosity about what lies beyond Putnam Pike is satisfied, its time to plan the next road trip.

Have an idea for a future road trip? Leave me a message.