Danbury, CT, approximately 70 miles northeast of New York City, was nicknamed Hat City for producing more hats than any other U.S. city in the 1800s. You can visit Tarrywile Mansion sitting on approximately 600 acres to take a step back in time. This ride follows the Housatonic River, taking you north into Litchfield County.
In the Litchfield Hills, you can soak in views of forests, local farms, and plenty of foliage. Heading west into Dutchess County, NY, you will follow the foothills of the Taconic Mountains and Hudson Highlands. Touring a portion of SR 22 in New York takes you by small hamlets, dairy farms, and the New York City Watershed. Finally, follow SR 202 back to Danbury.
When Pigs Fly South is a BBQ joint with mouthwatering treats, a patio, and vegetarian options. I recommend the pulled pork sandwich with a side of shoepeg corn pudding. Find it at 29 West Main St, Sharon, CT, (860) 492-0000.
Points of Interest
This cake-like structure is one of two spite houses in Connecticut. Built in 1961, this five-tiered building was constructed to express the owner’s frustration with the state. While you can’t enter, you can appreciate some of the details like the wrought iron barn door. Find it at 1 S Kent Rd, Gaylordsville, CT.
Kent Falls State Park
Along SR 7 is the tallest waterfall in Connecticut at 250 feet. Walk across a covered bridge to the base of the falls to take in the stunning view. After heavy rains or in the spring after snow melts, you may feel the spray as the water runs to meet the Housatonic River.
This eclectic hamlet, just off SR 22, features local and resident artist expeditions, festivals, classes, and lectures. History buffs will enjoy wandering through the historical agricultural buildings. Find it at 37 Furnace Bank Rd, Wassaic, NY, (855) 927-7242.