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Mohawk trail

Six Indian Trails That Turned Into Scenic Highways and Byways

The Indian trails that crisscrossed New England go back to prehistoric times.

Native Americans migrated from summer to winter homes along the paths, often worn bare by centuries of travel. They used the trails for hunting, trading and making war.

When the English colonists arrived, they owed a debt of gratitude for the Indian trails, wrote Chester B. Price in his book, Historic Indian Trails of New Hampshire.

“[T]hanks to the Indians, the early New Englanders inherited a vast network of trails which not only covered the New England states, but extended as far west as the Rocky Mountains,” Price wrote.

The Mohawk Trail and Kennebec Trail were two of the most famous Indian trails in New England. During the American Revolution, they were used for military maneuvers. Benedict Arnold followed both, the Kennebec Trail to his regret and the Mohawk Trail to his satisfaction – he captured Fort Ticonderoga at the end of it.

We identified six scenic driving routes that follow old Indian trails, at least one in each state. Some have been researched more thoroughly than others. If you know of scenic old Indian trails that can be driven today, please share them in the comments section.

The Old Connecticut Path

The Oliver Ellsworth House lies near one of Connecticut’s Indian trails.

The Old Connecticut Path was one of the most important Indian trails, stretching from Massachusetts Bay to the Connecticut River. In the early 1630s Nipmuck Indians loaded their surplus corn onto birch-bark backpacks and walked from the Connecticut River to Massachusetts Bay. There they traded their corn for copper and iron goods and woolen cloth.

John Oldham, whose death started the Pequot War, followed the Old Connecticut Path to explore the continent’s interior in 1633.

In 1636, the Rev. Thomas Hooker spent two weeks on the Old Connecticut Path with his followers to Hartford.

The Rev. John Wareham also led his congregation along the Old Connecticut Path to Windsor, Conn. John Adams followed that route from Tolland to Windsor in 1771. “Today I rode through paradise,” Adams wrote.

There is no consensus the exact location of the Old Connecticut Path from beginning to end, though genealogical researchers are working on it.

They concluded Adams took a part of the path that goes from the Tolland Green Historic District through the towns of Ellington, East Windsor and South Windsor. Then he went on to the Palisado Green in Windsor.

Generally, the Old Connecticut Path went through Massachusetts heading west along the Charles River in Cambridge, curved south in Wayland through Framingham, to Webster and to Lake Chaubunagungamaug. In Connecticut it continued to Hartford, Wethersfield and Windsor.

Today you can download apps that guide driving tours along parts of the Old Connecticut Path in Northeast Connecticut. You can follow John Adams’ route, or you can take other routes that go from Webster, Mass., to Tolland or Woodstock in Connecticut. Another Connecticut route goes from Woodstock to the Willimantic River. (Click here for more information about driving tours.)

Waldoboro Mast Trail (Route 220)

Downtown Waldoboro, which hasn’t changed much since this postcard was published, lies at the end of one of Maine’s old Indian trails.

Maine’s Indians used a vast network of canoe trails to get around, and to reach them they used a series of Indian trails from the interior to the coast. Carrying places, or portages, gave Maine tribes mobility throughout the region. It also let them trade extensively with each other and later with Europeans.

Indian paths from inland Maine to the coast also gave the Native Americans access to fur, birch bark and moose hide. One such path is known as the Waldoboro Mast Trail, which now follows Route 220 from Montville to Waldoboro. It was the most direct route from Lake St. George to the shellfish beds of the seacoast.

Wawenoc Indian families migrated along the path from the seasonal hunting camp to the seasonal fishing camp. They hunted for moose and beaver in the winter and brought their fur as trade goods to the coast using snowshoes, sledges and toboggans.

English settlers found the trail a convenient route to carry masts and spars for hundreds of the King’s ships built in Waldoboro.

Today Route 220 winds through rural Maine from Montville, which has several historic properties and the Frye Mountain Wildlife Management Area. It passes through the scenic towns of Liberty, home of Lake George and the Davistown Museum, and Washington. Travelers know Waldoboro for its commercial clutter on Route 1, which includes the popular eatery Moody’s Diner. The town itself has five nature preserves, a traditional downtown and eight sites listed on the National Register of Historic Places.

For a map of Route 220, click here.

Mohawk Trail

The Mohawk Trail.

The Mohawk Trail, one of the most famous Indian trails, today is one of the most beautiful drives in Massachusetts. Originally a trade route, it connected the Atlantic Indian tribes with the Iroquois tribes in Upstate New York and Canada.

The trail became a warpath when Mohawk war parties traveled it to destroy Pocumtuck settlements. Metacomet, or King Philip, took the Mohawk trail in 1676 to try to enlist the Mohawks in his cause (he failed). Benedict Arnold then took the Mohawk Trail on his way to capture Fort Ticonderoga.

In 1914, the Massachusetts General Court declared the 63-mile Mohawk Trail a scenic tourist route – the first in the United States.

Today Routes 2 and 2A follow the Mohawk Trail in Massachusetts from Athol to Williamstown. Boosters claim 100 scenic and culture attractions, including the Hail to the Sunrise statue, the Bridge of Flowers, a natural bridge, glacial potholes, pre-revolutionary homes in Old Deerfield, old growth forests and views of the Berkshire and Taconic Mountains.

Highway markers designate the trail. Click here for Mohawk Trail driving tours.

Winnicoek Trail

A seaside estate at Little Boar’s Head along one of New Hampshire’s many old Indian trails.

The Winnicoek Trail ran along the coast from the Merrimack River in Massachusetts through Winnicoek, now Hampton, and along the seashore to the Piscataqua River at Strawbery Banke, now Portsmouth.

The Pennacook and Abenaki Indians migrated along the path in the summer to what is now Odiorne Point. It’s a wooded park along the shoreline with sweeping views of the Atlantic Ocean and the Town of New Castle.

When the English colonists arrived in 1635, they used the Winnicoek Trail as a bridle path. Today it’s scenic Route 1A, also known as Ocean Boulevard, running along New Hampshire’s 18-mile shoreline.

Ocean Boulevard passes the wide, sandy beaches in Salisbury, Mass., and Hampton, N.H., then climbs a rocky promontory. Seaside estates begin at the Little Boar’s Head historic district and continue through Rye. Take a detour along Route 1B to wind through the quaint town of New Castle and past the grand old Wentworth-By-The-Sea Hotel. Route 1A finally ends in Portsmouth, a historic seaside city with many fine restaurants and Federal style homes.

Click here for a map of Route 1A.

Pequot Path

Route 1A turns into Ocean Road and the Narragansett Pier.

For hundreds of years, Narragansett and Pequot Indians traveled along the Pequot Path. It ran about 69 miles near the mainland shore from Providence to New London, Conn.

In 1636, Roger Williams took the Pequot path through Apponaug (Warwick) on his journey from Providence to the trading post at Cocumscussoc (near Wickford). “It is admirable to see what paths their naked hardened feet have made in the wilderness in the most stony and rockie places,” he wrote. Williams probably saw a dozen Narragansett villages along 20 miles of the path.

English settlers began using the Pequot Path until it evolved into the lower part of the Boston Post Road. Today, parts of scenic Route 1A (not to be confused with US Route 1A) follow the old Pequot path along the South Coast.

Scenic Route 1A follows the shore from Wickford to Narragansett, past the John H. Chafee Nature Preserve, a good spot to get out and walk to Narragansett Bay. Or, take a detour to the Gilbert Stuart Birthplace. The road passes large, exclusive homes, with views of the bay and the historic Casey Farm. FInally it feeds into Ocean Road past Town Beach to Narragansett Pier.

Click here to see how the Lower Post Road follows existing roads in Rhode Island.

Route 22A

Vergennes, a city that grew up along one of Vermont’s Indian trails.

Route 22A through the Lake Champlain Valley in Vermont was once part of a network of well-worn Indian trails linking villages and other overland trail networks. The western Abenakis of Vermont also used waterways such as the Connecticut River and Lakes Champlain and Memphremagog.

The St. Francis Indians came down from Canada along the trail by Lake Champlain to find warmer fishing grounds. The trail finally stretched to the Bronx, N.Y., where it became known as ‘the road to Bedford and Vermont.’ Today Vermont Route 22A is a continuation of New York Route 22A and a scenic drive in foliage season.

Route 22A goes from Ferrisburgh to historic Vergennes, Vermont’s oldest city. It then runs through Addison, Bridport, Shoreham, Orwell and Fair Haven on the New York border. Along the way lie the Chimney Point State Historic Site, dairy farms, rolling hills, white church steeples, and country inns.

Images: Old County Jail and Museum, Tolland, Conn. By Photograph by Greg O’Beirne – Own work, CC BY 2.5, https://commons.wikimedia.org/w/index.php?curid=1391441; Hail to the Sunrise, By This mediaToddC4176 (talk)Original workJoseph Pollia, 1893-1954. – self-made, CC BY-SA 3.0, https://en.wikipedia.org/w/index.php?curid=36285807; Bridge of Flowers By FFM784 – Own work, CC BY-SA 4.0, https://commons.wikimedia.org/w/index.php?curid=61250392; https://commons.wikimedia.org/w/index.php?curid=57432594; Little Boar’s Head By Teemu08 at en.wikipedia, CC BY-SA 3.0, https://commons.wikimedia.org/w/index.php?curid=1798424; Narragansett Pier By John Phelan – Own work, CC BY-SA 4.0, https://commons.wikimedia.org/w/index.php?curid=57432594.

This story about New England Indian trails was updated in 2023.

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The 6 Tallest Trees in New England

Once New England had the greatest forests and the tallest trees in the world. They were a major attraction for English colonists and their sponsors, who coveted the huge white pines as masts for the King’s Royal Navy. The Crown reserved the biggest pine trees, which government agents marked with three slashes called the King’s Broad Arrow.

The laws protecting the trees for the King were honored more in the breach than in the observance. Pine trees became a symbol of resistance, and images of them appeared in flags.

The New England Flag

Tall trees exercised a fascination over people apart from their political context. Societies formed to identify champion trees. And today, many states maintain registries of their tallest and biggest trees.

The Tallest Trees

In 1940 a nonprofit called American Forests started the National Register of Big Trees and named the Wye Oak in Maryland as the national champion for more than 60 years. But measuring the tallest trees isn’t always an exact science, and most champions yield their place to new specimens. Either another tree grows taller or the champion is felled by disease, weather or real estate developers.

We did our best to identify the tallest tree in each state. But who knows? A storm could have felled it since it was last measured. If you know of a tree taller than the ones mentioned – or if any of those trees have fallen – please comment below.

Connecticut’s Gold Standard

Pinchot Sycamore, one of Connecticut’s tallest trees.

The most famous tree in Connecticut, other than the Charter Oak, is the 104-foot-tall Pinchot Sycamore in Simsbury. It’s 28 feet around and at least 200 years old — if not 300 years old. It was named after Gifford Pinchot and officially dedicated to the conservationist in 1965.

The big old sycamore sits on the east bank of the Farmington River near the base of Talcott Mountain. Floodlights illuminate it at night, and canoers can launch their boats nearby. For a while the Pinchot Sycamore tied the largest sycamore with a specimen in Bath County, Virginia, until a bigger one in Ashland, Ohio, surpassed them both.

The Pinchot Sycamore, though, is not the tallest tree in Connecticut. That honor belongs to a 144.6-foot-tall white pine in a small forest in West Cornwall called Gold’s Pines, named after the man who purchased it in 1870, Theodore S. Gold. The forest grew to 46 acres, and then 56. It now belongs to the Housatonic State Forest as one of the few old growth forests in Connecticut.

“Here, even on the brightest of blue sky days, the gentle wind makes a thunderous noise as it passes through,” wrote one hiker who waxed elegiac about the canopy of the ancients.

You can reach Gold’s Pines on Rte. 128, just right of the Little Guild of St. Francis animal shelter. Gold’s Pines also boasts a 127.8-foot-tall Tulip tree.

Maine’s Unofficial Champ

Yarmouth Dutch elms, possibly the tallest trees in Maine once.

There are no reliable height measurements in Maine available, according to the Monumental Tree index. Maine has its own registry of big trees, which it updates periodically but is considered unreliable. Maine residents nominate trees for the honor of appearing in the registry. The 120-foot white pine in Morrill is the unofficial tallest tree in Maine.

Maine, however, can claim the tallest chestnut tree in North America. The tree is 115-feet high, 20 feet higher than its closest competitor. Only a few dozen chestnut trees remain in Maine, as chestnut blight wiped out large stands of the trees from Maine to Georgia in the early 1900s.

The chestnut was discovered last year in a forest in Lovell, near the New Hampshire border. The forest was once part of an artist colony, Hewnoaks, founded by artist Douglas Volk (1856-1935) and his wife. Volk’s wife donated the property to the University of Maine Foundation.

Maine was once home to the largest Dutch elm tree, nicknamed Herbie. Planted in 1793 on Main Street in Yarmouth, Herbie grew to 110 feet tall with a circumference of 20 feet. Children watched some of its diseased limbs being cut off and cried, “What are you going to do to Herbie?”

Herbie finally succumbed to Dutch elm disease and fell to the ax and chainsaw on Jan. 19, 2010. A section of the trunk’s base was displayed at the 2010 Yarmouth Clam Festival. You can now see it outside Yarmouth’s town hall.

Jake Swamp

Along the Mohawk Trail, where you’ll find some of Massachusetts’ tallest trees.

The tallest tree in Massachusetts has a name: Jake Swamp. It’s a 163.2-foot white pine in the Trees of Peace Grove in Mohawk Trail State Forest. The forest, located in Charlemont, Hawley, and Savoy, has 83 trees reaching 148 feet, the largest collection of tall white pines in New England. It was discovered by Robert Leverett, a big-tree hunter and co-author of The Sierra Club Guide to Ancient Forests of the Northeast.

In 1996 Leverett helped found the Eastern Native Tree Society. Its members search for old stands in remote places and for giant trees in parks and cemeteries. When Leverett discovered the tallest white pine in Massachusetts, he named it after Mohawk Chief Jake Swamp Tekaronianeken.

Jake Swamp founded the Tree of Peace Society in 1982. He traveled around the world planting Trees of Peace near places such as the National Mall in Washington, D.C., and Constitution Hall in Philadelphia. A year after his death in 2010, trees were planted around the world on October 18 on what would have been his 70^th birthday. A Tree of Peace was planted in his honor in Huntington Park, Mass.

Reader Norman Schell personally measured another giant tree in Massachusetts: the Sycamore on Rte. 47 in the center of Sunderland. A sapling when the United States ratified the Constitution, it measures 32 feet in circumference. It is acknowledged as the oldest and largest Sycamore tree east of the Mississippi.

New Hampshire’s Skinny White Pine

White pines, probably the tallest trees in New Hampshire if not all of New England.

The tallest tree in New Hampshire is a white pine measuring 166.1 feet tall on a private estate in Claremont. It was declared the new New England champion by the Native Tree Society. It’s a mystery to us who owns the estate, but if you’re in Claremont just look for a tall stand of white pines. The tallest one is ‘extraordinarily skinny,’ according to Robert Leverett, one of the men who measured it.

There were also extraordinarily tall white oaks in the Claremont stand. “The 115.2-foot white oak blew my mind,” wrote one big tree hunter. “The growing conditions have to be superb to support such a height for white oak so far north.”

Additionally, the Bradford Pines Natural Area in Bradford has trees over 200 years old and over 150 feet tall. Randy Redford believes they may be the tallest trees in New Hampshire, if not all of New England. They even have lightning rods on them.

A sugar maple in Ossipee was believed to be the biggest in New England until it fell in 1846. It yielded 3,300 board feet of lumber and nine cords of firewood.

According to legend, a pine cut on the site of Dartmouth College reached a height of 240 feet. But many doubt the species can grow so tall.

The Mighty Tulip

Tulip trees, the tallest trees in Rhode Island.

Several tulip trees have been identified as Rhode Island’s tallest tree.

According to the Cranston Herald, the tallest tree in Rhode Island is at 975 Warwick Neck Ave. in Warwick. The Rhode Island Champion Tree List of 2014 shows a Warwick tulip tree measuring 126 feet high as the tallest in the state.

The Native Tree Society, however, claims a 115.7-foot tulip tree on the ‘Nathaniel Green’ site in Kingston. They could be referring to the University of Rhode Island Campus.

The tulip tree has large flowers that sort of resemble tulips. Sometimes it’s called a tulip poplar or yellow poplar, but it’s actually related to the magnolia. Indians hollowed out its wood to make canoes from its light wood, and sometimes people refer to it as a canoewood tree.

The fattest tulip tree, measuring 16 feet around, is in Bristol. Click here for a map of a walking tour of the town’s historic district, where the tree resides.

Vermont’s White Pine

A tall white pine

Vermont’s tallest tree is a 143.4-foot white pine in Arlington, according to the Eastern Native Tree Society. It’s tucked in among one of the state’s best collections of large-diameter white pines, the Fisher-Scott Memorial Pines Natural Area. There they are safe from development.

The Fisher-Scott Memorial Pines Natural Area was a 1975 gift to the state from the heirs of Vermont writer Dorothy Canfield Fisher. Fisher, a tireless social activist, promoted education and prison reform. Though originally from Lawrence, Kansas, Fisher adopted Vermont as her home state.

The Arlington property that is now a protected wildlife area served as Fisher’s writing retreat during a career that produced more than 40 books, both nonfiction and fiction (largely set in Vermont).

Vermont takes its champion trees seriously. The state keeps a registry of its biggest and tallest trees by town and species, from the Dwarf Chinkapin Oak in Bridport to a giant Cottonwood in Hubbardton. To check it out, click here.

You can visit the Fisher-Scott Memorial Pines Natural Area on Route 7A just north of Arlington.

Photos: Pinchot sycamore: By Msact at English Wikipedia, CC BY-SA 3.0, https://commons.wikimedia.org/w/index.php?curid=48227856. Pinchot sycamore with people By Marty Aligata – Own work, CC BY-SA 4.0, https://commons.wikimedia.org/w/index.php?curid=56461629. Tulip tree: By Timothy Valentine – http://www.flickr.com/photos/el_ramon/3583585898/in/set-72157614131871676/, CC BY-SA 2.0, https://commons.wikimedia.org/w/index.php?curid=6945589; White pine bough, By DigbyDalton – Own work, CC BY-SA 3.0, https://commons.wikimedia.org/w/index.php?curid=28948041. This story about the tallest trees in New England was updated in 2023.

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