Home Spotlight SeriesNew England Places Six Indian Trails That Turned Into Scenic Highways and Byways

Six Indian Trails That Turned Into Scenic Highways and Byways

They make it hard to keep your eyes on the road


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. 


Sally Lobkowicz September 23, 2017 - 10:47 am

Thank you! I have lived in Waldoboro for 40 years and had never heard Rt.220 called this – makes perfect sense!

Alberta J Vargas September 24, 2017 - 4:58 pm

. . . And we think of New England “history” beginning in 1620?

James W. Gould September 28, 2017 - 10:07 am

One of the most beautiful roads in America is the Old King’s Highway, Route 6A on Cape Cod. It follows an earlier Indian Trail from Sandwich, through Barnstable, Yarmouth, Dennis and Brewster. Enjoy!

Leslie Landrigan September 28, 2017 - 10:10 am

Thank you for pointing that out. It’s one of our favorite routes, and we often take it from Sandwich to go shopping in Orleans at Snow’s and then have lunch at Land Ho — though there are many fine eateries along the way.

Elaine Purdy October 3, 2017 - 2:53 pm

Please don’t forget the old Crown Point Road that followed the ancient Indian path crossing Vermont and connecting sites on the Connecticut River to Lake Champlain. Perfect route for the overland journey from the New England coast to Quebec and Montreal.
Elaine Purdy, Historian, Crown Point Road Association

Comments are closed.

Subscribe To Our Newsletter

Join our mailing list to receive the latest artciles from the New England Historical Society

Thanks for Signing Up!

Subscribe To Our Newsletter

Join Now and Get The Latest Articles. 

It's Free!

You have Successfully Subscribed!