Seasons Magazines

Seasons Magazines

Hiking Through History in Connecticut: A Lasting Legacy

Preserving Nature’s Legacy

As nature lovers explore the hiking trails of Connecticut with a bent toward history, they can’t help but reflect upon more recent colonial events that took place within these forested pathways. Yet it is also important to think deeply about the ancient Native American history of this area founded by the first residents of our state. The term “Connecticut” means “beside the long tidal river,” derived from the Algonquian word, “quinnehtukqut.” Native Americans first blazed most of the present-day hiking trails as they hunted migrating animals.

These forested arteries then developed as trade and transport routes by the colonists thousands of years later as the early European settlers began to wrest away the land from those who originally resided here. Presently, those who live in the Nutmeg State of all backgrounds and nationalities have become passionate about curating the land, preserving the trails, and rebuilding those that need work. They are devoted to educating the populace that when hiking through state parks and recreational sites, people should keep in mind that this legacy is part of a great nation dating back 12,500 years, long before colonial settlers arrived.










Legendary Hikes & Tall Tales

The Hanging Hills

Hubbard Park

Meriden, CT

Historical trails throughout the state of Connecticut have become pathways weaving together folklore and legends of memorable tales, some taller than others. Our Connecticutians just adore a good story about the supernatural, as did their British, Welsh, and Scottish forbears famous for blarney, exaggeration, and fanciful imagination. Among all the historical trails in Connecticut, one of the most notable, charismatic places seems to be the Hanging Hills of Meriden.

The Hanging Hills border the Quinnipiac River, where Misery Brook and other aptly name landmarks stipple the dramatic scenery. Steep cliffs and mind-blowing views have inveigled nature lovers to this terrain with Jurassic rock-scapes. For over 100 years, hikers have told the strange tale of a lone, mute black dog, small in aspect, said to often appear on the trails near West Peak. Those who claim to have seen the dog describe it as a supernatural creature who supposedly leaves no footprints and remains completely silent as it travels along the ridges of Meriden’s Hubbard Park. They claim it lurks on the trail and can be seen from the ridges here and there when you least expect it. What is particularly ominous about the spectral creature is the ill-omen that goes along part in parcel with the sighting: “If a man shall meet the Black Dog once, it shall be for joy; and if twice, it shall be for sorrow; and the third time he shall die.” These words were written up in a beguiling mystery thriller published in The Connecticut Quarterly of 1889, by W.H.C. Pynchon, grandfather of the celebrated author Thomas Pynchon.

In truth, Hanging Hills can be somewhat sinister as it craftily beckons nature lovers and geologists to its hazardous edges. Do you know anyone who claims to have seen the Black Dog of West Peak who also has an unshakable attachment and fear for this spot? I do…and have read many recent accounts of encounters with this mysterious creature on social media. Is this a case of a tall tale that people believe because the work of fiction that represents it is so palpable?

When visiting the Hanging Hills, be sure to feast your eyes on Castle Craig, a 32-foot-high structure resembling a turret from a fairy tale that Rapunzel would be proud to throw down her hair from. It looms over an expansive view of the Meriden cliffs from a vantage point 976 feet above sea level. A metal stairway on the inside of the turret permits hikers access to the outside observation tower. From there, one can take in the view of Long Island Sound, New Haven, and even the Berkshire foothills (weather permitting).

Machimoodus State Park’s Mysterious Noises

Moodus, CT

Nature beckons people to go hiking and bird watching on the beautiful woodland trails of Machimoodus State Park in East Haddam. But while you’re meandering within this 300 acre Eden, be sure to keep your ears open in case you might hear unearthly strange sounds that have been emanating from the ground in this region for centuries. Those who lived at the foot of Mt. Tom found these unsettling, harsh noises to be mystifying. Local inhabitants once felt like they were victims in a horror story. When Native Americans occupied the lands at the intersection of the Connecticut and Salmon Rivers, they named the area Machimoodus which means: “place of bad noises.” The startling sounds still come and go, quite mercurial, never too predictable. What could they be?

The Puritans mentioned having been plagued by groaning booms, vibrations, and furious sounds. Naturally, they attributed that to dark demons and devils in accordance with their folktales and religious fears. But they weren’t the only ones bewildered for centuries. The Wangunk Indians, who had their fair share of these same terrors, attributed it all to their god, whom they hoped to appease with offerings. They believed that Hobomoko, who sat on a red sapphire throne underneath Mt. Tom, was the responsible party. Some said he was angry over the invaders coming to take over the land. Or he could have been watching good and bad witches within the “hall” of his American “mountain kingdom” in their battles with each other. No one seemed to know for sure.

Now, modern science knows the sounds are caused by what they call “earthquake swarms,” tiny shallow earthquakes responsible for this entire hullabaloo.


Sleeping Giant State Park, Mount Carmel


Sleeping Giant Park got its name first and foremost from the fact that the rolling hills above Hamden have an uncanny resemblance to a reclining giant embedded into the hills when viewed from a great distance. The story of the Giant begins with a Quinnipiac legend of Hobbomock, a passionate character who taught his people how to hunt and fish, then departed to teach these skills to others. After many years, he returned and somehow became infuriated over the way his people were misbehaving. He stamped his foot down and caused the Connecticut River to suddenly divert to the East in Middletown after flowing South for over a hundred miles.

Good spirit Keitan came to the rescue by casting a powerful spell over Hobbomock, causing him to sleep soundly among the Connecticut hills. In 1735, the small settler’s community of Mt. Carmel was first built near a mill along the river near Joel Munson’s dam. Later, a profusion of 19th-century back-to-nature painters and transcendentalist writers like Emerson and Thoreau created a renewed interest in the benefits of living among the mountains. Metacomet Ridge became home to summer cottages. A carriage road on the “Giant” gave rise to Blue Hills Park where John H. Dickerman’s road enabled visitors and locals to enjoy picnics on the high ledges.

On June 18, 1876, a 12-year old boy, Arnold Dana, fell off the cliffs at Sleeping Giant. Unbelievably, the boy lived and decided that since the giant was good to him, one day he’d be good to the giant. The Mt. Carmel Traprock Company started quarrying there earlier in 1912, but when the plan began to endanger the ridge (the Giant’s Chin) with blasts, the beauty of the region was threatened. Public outcry took form as the Sleeping Giant Park Association (1924). A year later, a state park was established after the Sleeping Giant Park Association transferred the land to the state. The boy who fell off the cliff and lived became the president of the Sleeping Giant Park Association. His sincere efforts to preserve the giant resulted in silencing the quarry blasts on the chin and acquiring the lands in perpetuity, preserving the park for all to enjoy.


Strange But True

The Leatherman’s Cave-Mattatuck State Park-Watertown

A cast of unforgettable characters has traipsed through the Connecticut highlands but none have captivated the imagination quite like the eccentric Leatherman who appeared in our state around 1860.  For no apparent reason, from 1883 to 1889, this man clad in a heavy patchwork of leather scraps weighing 60 pounds trod a 365-mile loop every 34 days between Connecticut and western New York State. That amounts to 11 times per year. He only halted on this circuitous route to eat and sleep. It is said that housewives could tell time by the moment he arrived at their homesteads asking for food at the exact appointed hour each month he was due in. Some have said he was basically a “walking calendar,” others now muse he suffered from Obsessive Compulsive Disorder caused by trauma. During his sojourn in Connecticut, locals gladly fed him and affectionately baked him fresh bread before saying goodbye until the next time. He had a circuit of caves where he slept, as he was never known to stay anywhere with a host. Quiet and nearly mute, he trod with a heavy backpack full of leather crafting gear, a wooden hand-carved pipe, and a French prayer book.

Rumors abounded as to the whys and the wherefores. Books have been written about him and first-person accounts of his appearance all over the state of Connecticut were handed down through generations. One story said he was a Frenchman fleeing his country after heartbreak struck. Others said he was raised by a Native American Grandfather in Canada then made his way south after the passing of his French Canadian family. One thing is certain though; the Leatherman was a real person, although when you first hear about him, you can’t imagine it could be true.

The most spectacular cave on his 365-mile loop at Mattatuck Park isn’t so easy to access but accordingly, it is well worth the effort. At the summit, take in the breathtaking bird’s eye view from Crane’s lookout, the “penthouse” just above the jumbled mass of stones that gave the Leatherman protection from the elements. The blue-blazed markers point you in the right direction through the level and steep combination of the trai, but bring a map or app. to make sure you don’t get off track.

In 1889, worried townsfolk in New York State discover that The Leatherman had passed away in one of his caves there, probably due to mouth cancer caused by his incessant pipe smoking. He was given an honorable burial, and although exhumed once due to the absurd amount of traffic caused by mourners and curiosity hounds, he now rests in Sparta Cemetery in New York State. His tombstone simply reads: The Leatherman.

Will Warren’s Den/Rattlesnake Mountain, Farmington

Along the 50-mile Metacomet Trail near Route 6 in Farmington, a 1.2-mile hike into the hills leads to a notorious hiding place. In the mid-19th century, Tunxis peoples occupied these high jagged cliffs, and already land altercations between the Native Americans and the settlers had been brought forward to the Connecticut General Assembly around that time.

Legend tells of a mysterious farmhand named Will Warren who sounds like a Huckleberry Finn kind of guy. He refused to attend church, spending his free time with the few Native Americans that lived on the outskirts of Farmington going fishing, hunting, and trapping. One version of the story is that the townspeople took objection to the notion Warren refused to attend church on the Sabbath and flogged him for blasphemy. Another, put forth by the Farmington Land Trust, tells that Will was a thief who stole some sheep and was whipped for it. He set fire to the village of Farmington in revenge. Will fled to what is now known as Rattlesnake Mountain, the enraged farmers hot on his trail. Two Native American maidens just happened to be at the top of the mountain, where they ushered him into a sequestered cave, brushing away his footprints just in time so the villagers passed right by the small entrance to the cavern. Foiled again! Warren’s cave is quite difficult to access for its narrow entrance points, one being of a vertical drop into the dark opening that reveals a secondary chamber amid massive boulders.

Not too terribly further along the Metacomet Trail is a place of great historical significance called “Hospital Rock.” The flattened rock was near a smallpox hospital where patients who had been quarantined in the late 1700s could meet with their families during their recovery period. The rock is an archaeological site of great significance and deserves more formal protection. Approximately 66 names of smallpox patients were carved with great effort into the hard stone. Many are difficult to make out but others are quite clear and bear witness to the names of people from that time period who wanted to leave their memory for posterity. Pinnacle Rock is along the same trail, providing a sweeping 360-degree view of the valley below…time for the panorama setting on the smartphone.


Sympathy for the Devil

Speaking of the Devil, Connecticut nomenclature seems to have a penchant for the namesake with about 30 places bearing the name. In fact, you could have a picnic breakfast at Devil’s Hopyard, take an inner-tube ride in Satan’s Kingdom before lunch, go fossil hunting in Devil’s Den Nature Preserve (to search for a legendary cloven hoof print purported to have been left by the Prince of Darkness himself), then head out to Spooky Hollow for stargazing. Perhaps the most popular of all these is a locale steeped in history and characterized by stunning mysterious formations below some waterfalls.


Devil’s Hopyard State Park-East Haddam

This state park offers swimming, hiking, birding, fishing and camping but also sports a colorful name difficult to forget. Acquired in 1919, the land features 1000 acres nestled within the Millington section of Haddam. The Eight Mile River’s Chapman Falls entices visitors with its 60-foot drop over a Scotland Schist formation of stone steps. The power of the falls once ran Beebe’s Mills, which operated until the mid-1890s. During the Revolutionary War era, Dr. Beebe was tortured, tarred, and feathered for his outspoken loyalty to England. His colonial-era gristmill was damaged, and the stone was thrown into the river. Although there has been some controversy over the historical recounting of this incident, it is now widely acknowledged that the mill’s grinding stone was cast downriver by a mob associated with groups such as the “Sons of Liberty.” DEEP removed the millstone to prevent modern adventurers from trying to access it in a dangerous place for photos and dares. The broken stone now is on display in a permanent exhibition entitled: “American Democracy—A Great Leap of Faith” at the National Museum of American History in Washington, D.C. This Connecticut millstone tells a powerful story highlighting difficulties colonizers had with each other during the Revolutionary War period as well as during the War of 1812. Violent groups backed those who would eventually espouse free speech and protection of personal property. Leaders for independence in higher realms considered people like Dr. Beebe collateral damage in their effort to achieve independence, but would later write up the Bill of Rights to prevent these abuses.

There are several anecdotes floating around as to how the area received its current name. Perhaps the most interesting is the tale related to the perfectly cylindrical potholes in the rocks that have developed near the spectacular falls. Some are inches in diameter while others are several feet wide. The early settlers believed that the Devil passed by the falls and got his tail wet. Infuriated, the demon hopped around boring holes into the rocks with his angry tail. Geologists now understand that stones moving downstream got trapped in the eddy of currents, spinning around to form the strange circular depressions. As the rock indentations wore down, they’d catch another and another stone within their scooped dish enlarging the formation each time.


Castles n’ Caverns

Judges Cave/West Rock Ridge State Park-New Haven County

Back in good ole’ 1649 way before the Revolutionary War, fifty-nine British judges sentenced King Charles I to death, thereby dissolving the monarchy and placing Oliver Cromwell at the helm of the British nation. Charles II, son of the executed king, was placed back upon the throne eleven years later.  Vengeful, Charles II demanded that each regicide convict be hanged, drawn and quartered, a surprisingly popular but grisly punishment at the time. Three of those judges fled to North America. The newly crowned monarch sent his henchmen hot on their heels, so they hid in New Haven backed by sympathetic Puritans. As they began to fear recognition by royal informants amid the intrigue, payoffs, and shifting allegiances, they fled to a small natural cavern atop West Rock Ridge. According to the story, they survived on food scraps brought by sympathizers, but eventually after a time, they encountered a panther, forcing them to flee the area and head to Massachusetts. The cave is named after the judges; the path leading up to their rocky retreat is called Regicides trail. The jumbled mass of boulders that comprise the cave entrance are emblazoned with a plaque which reads, “Here May Fifteenth 1661 and for some weeks thereafter Edward Whalley and his son-in-law William Goffe, members of the Parliament-General, officers in the army of the Commonwealth and signers of the death warrant of King Charles First, found shelter and concealment from the officers of the Crown after the Restoration. ‘Opposition to tyrants is obedience to God,’ 1896.”


Heublein Tower at 

Talcott Mountain State Park


No article about Connecticut historical hiking trails would be complete without mentioning Talcott Mountain State Park and recommending a visit to see Heublein Tower. Talcott Mountain was named after John Talcott, the founder of Hartford. The Heublein Tower we see today is half castle, half lookout, a one-time summer residence for the family of Gilbert Heublein, the son of a wealthy Hartford immigrant from Germany. One day, during his courtship, Gilbert went hiking with his fiancé in the Talcott Mountains. Atop the peak, feeling amorous, he vowed to build her home there someday. The monolithic marvel that came to fruition became Heublein’s prestigious private residence. Inside, there are luxury bedrooms and a ballroom on the 6th floor where the lookout viewing area is today. Heublein was a successful businessman having founded a Hartford Hotel, and later with the zest of a true entrepreneur, he began manufacturing A-1 Steak Sauce.

Today “The Heublein” presides over the Farmington Valley. You get there by taking a somewhat steep hike with stunning lookouts along the way. On a clear day, ‘you can see forever,’ as the song goes, and this applies perfectly to the top of the mountain, especially when the Tower is open to the public. You may find yourself short of breath climbing the inside stairs to get to the top, but since you’ve gone so far, it’s a must to access the viewing area when possible. Due to COVID-19, the Tower has been open and closed to the public at various times, but no matter when you go, it is enough to simply get there and to enjoy the exterior architecture completed in 1914. Look for musical festivals at the Tower such as the upcoming August “Hike to the Mic” event the the “Tower Toot” where musicians come to play all day long as vendors cook up sausages and other tasty treats for hungry music-loving hikers. The Friends of Heublein Tower have worked hard together with the Department of Environmental Protection to ensure the property and surrounding forests are well cared for, while ongoing plans for continued restoration of the Tower remain high on the list of priorities.


Gillette Castle State Park-East Haddam/Lyme

The early part of the 20th century was a good time to build castles in Connecticut, apparently. William Hooker Gillette was the son of prominent Hartford elites as well as wearing the hat of actor, playwright and inventor. He began building his castle in 1914. His home still presides over a large estate and closely resembles a medieval castle of complex stone walls, turrets, artisan woodcarvings and unique furnishings. It took 25 men over five years to complete this architectural fantasy world. Now protected as a State Park, surrounding pathways wind through woodland trails that stretch over Gillette’s private train trestles, into caves, along near-vertical rocky steps, and past stone arched bridges. Situated on a hill above the Connecticut River, the Castle has a bird’s eye view of the natural banks characterizing the waterway. The Connecticut River is the only major river in the Northeast that doesn’t have a well-developed town at its’ mouth or extensive commercial development due to extensive shifting sandbars. The eagle-eye vantage point from the Castle’s cliffs give one a sense of how things looked 100s of years ago. And isn’t that brief foray back in time part of what we all love to see when hiking in our state?


Heroes and Their Journey

Barn Island-Stonington

This extraordinary place is full of well-maintained hiking trails, lush meadows, sandy beaches, tidal marshes, rocky coastal uplands, and forests. The enchanting coastal landscape engages naturalists and hikers where deep orange dusky evenings abound with birdlife. Barn Island seems to transcend space and time. The wetlands are perhaps the finest in the state according to the late William Niering, author and renowned Connecticut College botany professor. But asides their natural splendor, this place witnessed history in the making back in the 18th century when former slave Venture Smith had a chance to start his life anew by making Barn Island his home.

Captured by slave traders in Africa as a 7-year old prince, Venture Smith, formerly Broteer Furrow, saw his well-respected father brutally tortured and killed for refusing to reveal the hiding spot of the villager’s monies they accrued from trade. Forced to march days on end to the coast, Broteer was soon separated from his mother and his once close-knit family. The African prince was then sold to work on a ship heading for Rhode Island as a servant. The price paid for the brave 6-year-old child was 4 bottles of whisky and a piece of calico. In 1739, Broteer (later known as Venture Smith) arrived in the colonies where he spent untold years working his way out of bondage while toiling for farmers on Barn Island and Fisher Island across the Sound. He was a legendary personage of strong build and unshakeable determination who later built his own homestead farm on Barn Island.

Broteer worked double duty farming and chopping wood until he became prosperous enough to purchase his wife and family from slavery. He bought other countrymen and freed them as well, although many some whose freedom he bought betrayed him with theft and promises not kept. Through all this, Broteer maintained his dignity, honesty, and work ethic. His word, once given, could always be counted upon, and his charisma was so compelling that even the harsh slave owners made allowances for his requests. His family was eventually settled in East Haddam where he wrote his memoir before passing away in 1805. His thoughtful memoir is considered one of the earliest works by a former African forced into slavery. He said: “My freedom is a priviledge that nothing else can equal.” Venture’s adventures and exploits are highlighted in an exhibit at the Smithsonian National Museum of African American History and Culture. When you walk along the trails of Barn Island, be sure to stop for a moment of silence to reflect on this heroic man of courage who bought his freedom then went on to free many others.

The Stonington Historical Society Lighthouse will be featuring a Venture Smith Exhibit this spring that hikers can go visit after a day on the trail.


Pachaug State Forest – New London County 

Pachuag State Forest and the river that runs through it once teemed with historical intrigue, war, and betrayal. Now, it is home to countless trails that wind throughout the Eastern portion of the state stretching all the way to Rhode Island. Connecticut’s expansive state park was originally established in 1928 with 1,011 acres of land purchased from the Briggs Manufacturing Company in Voluntown. This old town was named for the volunteers in the 1675 wars who stayed to fight the Native Americans. Pachaug State Forest, located in New London County, spans 26,477 acres in six towns, being the largest state forest in Connecticut.

The word “Pachaug” is a Native American term that means “bend or turn in the river. From nine miles at the Beach Pond source of the river to its junction at the Quinebaug River, the Pachaug River traverses twice that distance while winding through the varied landscapes. In 1973, the Pachaug-Great Meadow Swamp received the National “Natural Landmark” designation, now considered one of the finest Atlantic white cedar swamps in our state.

Before the colonists arrived, Pachaug Forest was the tribal land of the Pequot, Mohegan, and Narragansett, people. One of the great Native American leaders at the time, Wampanoag Sachem Metacom, also known as Metacomet or “King Philip,” (the name given to him by the English) led an uprising. Metacom took a British name and at times wore Western-style clothing to improve relations with the British while attempting to make sure the colonizers honored territorial treaties. However, war became inevitable in response to the expansion of colonists into sacred territory, a fact that deeply disheartened and infuriated the Wampanoag, Nipmuck, Pocumtuck, and Narragansett tribes. King Philip’s War (1675-1676) was the last major endeavour by the Native Americans of this region to expel the English settlers who were breaking treaty provisions. A devastating, bloody conflict arose when the Mohegan, Pequot, and Nauset tribes joined with the colonists. One out of ten soldiers on both sides died. John Alderman, the Native American soldier who fought alongside the colonizers, shot and killed King Philip on August 20, 1676.  The bloody 14-month-long war ended with the death of Chief Metacom. Beheaded, drawn, and quartered, Metcom’s head was placed on a spike and displayed for 2 decades in Plymouth. Many hundreds of colonists had died and their settlements had been destroyed. But thousands of Native Americans had also been killed; colonizers decimated the Wampanoag, the Narragansett, and other smaller tribes. King Philip’s war fought on these lands ended much of the Native American resistance in Connecticut, leading the way for more English settlers to occupy lands previously granted by treaty to the earliest residents of the land. Many captives were sold into slavery as prisoners of war.


So, Who’s Land Is it Anyway?

While hiking through the stunning trails of Connecticut one fine day, you might find yourself cheerfully humming the Woodie Guthrie song “This Land is Your Land,” that popular folksong many learned in grade school. But when Guthrie intoned: “This land was made for you and me,” perhaps he had, a certain blind spot within his thinking process.

There is truly a sense among New Englanders nowadays of a deep apology and regret for how some of the early settlers affected the Native Americans. War, pestilence, and the introduction of strong alcohol in trade and bribery took a terrible toll. But if you refocus your lens just slightly, you will know that the Native American spirit is here in our hills everywhere for eternity, from the paths they first blazed to the many people living in our state of all backgrounds that proudly claim heritage with Connecticut’s first occupants.

We remain a state with countless rich layers of history here in the forests of Connecticut, from modern-day folktales and colonial lore to Paleo-Indian legends. All these compelling stories can’t help but fascinate hikers in their Patagonia jackets with Eddie Bauer backpacks, reminding them of who once walked here and developed this land to begin with.

Take a Hike!