The Strangest Road Names in Connecticut and How They Got Them
Driving through Connecticut, travelers quickly notice that some road names defy the ordinary, hinting at quirky histories and local lore that invite deeper exploration. Just outside Hartford, in the historic town of Wethersfield, you’ll find Silas Deane Highway, named after one of Connecticut’s first diplomats. This stretch connects to a quieter, curiously named side road known as “Dead Man’s Curve.” The moniker stems from a treacherous bend near the Connecticut River that once claimed multiple accidents when horse-drawn carriages dominated transportation. Walking or biking along the nearby Wethersfield Cove trail, visitors can enjoy scenic water views while pondering how this dangerous curve earned its grim nickname in a town that dates back to the 1600s.
Heading southwest about 20 minutes from New Haven, the village of Guilford showcases a charming example of local naming whimsy with “Save the Trees Road.” Near the Guilford Green, a historic town center famed for its well-preserved colonial architecture and leafy parks, this road’s unusual title originated from a 1970s conservation effort. Residents rallied to protect a line of ancient oak trees slated for demolition during road widening. Strolling the Green in autumn, visitors experience a perfect blend of history and nature, where the very street names tell stories of community activism and a deep respect for the environment.
In northeastern Connecticut, 30 minutes northeast of Hartford, the town of Stafford is home to a place called “Hell Hollow Road,” a name that captures the imagination immediately. This narrow, forested lane leads off the Stafford Hollow area and is surrounded by thick woods and wildlife. The evocative name is thought to derive from early settlers’ descriptions of the harsh winters and rugged terrain that made the area feel almost otherworldly. Nearby, the Shenipsit Trail offers a moderately challenging hike through the same dense forests, culminating in views from Soapstone Mountain. Spring and fall bring vibrant foliage that contrasts starkly with the eerie name, creating a vivid natural drama for visitors.
Along the scenic Route 169, about 50 minutes northeast of Hartford, lies the town of Brooklyn, home to the intriguingly named “Monkey Farm Road.” While no monkeys ever lived there, the name reportedly comes from a local farmer’s misadventure involving curious livestock and a makeshift enclosure. Brooklyn itself is known for its rural charm and the nearby Roseland Cottage, a striking Gothic Revival summer home with beautifully maintained gardens. Exploring the cottage grounds in early summer, when the flowers bloom and the road names prompt chuckles, reveals a quieter side of Connecticut’s rural heritage, far from urban bustle.
Closer to the coast, in the town of Mystic, about 90 minutes southeast of Hartford, a street called “Whale Oil Row” recalls the region’s maritime past. This thoroughfare runs near the Mystic Seaport Museum, where visitors can immerse themselves in the world of 19th-century whaling and shipbuilding. The name “Whale Oil Row” reflects the importance of whale oil as a vital commodity for lighting and industry during that era. Touring the museum’s historic vessels and working waterfront in late spring or early fall provides a tangible connection to the road’s evocative name and the town’s seafaring legacy.
In the southern part of the state, roughly 35 minutes northeast of New York City, the town of Ridgefield features “Cemetery Lane,” nestled near the historic Ridgefield Cemetery. This peaceful lane leads to the resting place of many Revolutionary War soldiers and local notables, making it a solemn but fascinating stop. Walking the cemetery grounds during the crisp fall months, when fallen leaves create a quiet carpet underfoot, visitors can reflect on how such straightforward place names sometimes serve as portals to profound local history and remembrance.
Further east, in the university city of New Haven, home to Yale and about 80 miles southwest of Hartford, “Whalley Avenue” stands out among the city’s many evocative street names. Named for a prominent 19th-century minister and abolitionist, this avenue slices through diverse neighborhoods where history and culture intersect. Nearby, the Yale University Art Gallery showcases collections that include works from the colonial era, bridging the past and present. A walk on Whalley Avenue paired with a visit to the gallery in late afternoon sunlight reveals the layered stories embedded in the city’s geography and architecture.
Finally, in the town of Granby, about 30 minutes north of Hartford, “Scotland Road” hints at the roots of early settlers who brought their Scottish heritage to the Connecticut River Valley. This rural route passes through pastoral lands and leads toward Salmon Brook Park, where the accessible walking trails and fishing spots draw families and outdoor enthusiasts alike. Visiting in the spring when wildflowers bloom and the air is fresh offers a peaceful appreciation for how immigrant histories are woven into the fabric of place names and landscapes across the state.
From riverside bends to wooded hollows, Connecticut’s strangest road names invite travelers to uncover stories of danger, preservation, heritage, and industry. Each name anchors a slice of local life, waiting to be experienced on foot, bike, or by car, turning an ordinary drive into an engaging journey through the state’s mosaic of culture and history.