Longfellow Square is Where the Theodore Roosevelt International Highway Begins

This postcard states State Street from Longfellow Square in Portland,
Me. This is the starting point of the 4,060 miles of the

Theodore Roosevelt International Highway.

Collection of PWM

Updated - 7-9-2026

Click here to view the history of creating and the dedication of the Longfellow Statue

May 31, 2026, Joe Banavige released this wonderful American 250 Tribute to William W " Bill" Sewall, TR's Maine guide (along with Wilmot Dow, Bill's nephew) 

Click Here to see Joe's Substack post

      New in 2022 - First Post for the Theodore Roosevelt Maine Heritage Trail - June 16, 2022

      First Look at Logo - "My Debt To Maine" - Logo - Theodore Roosevelt Maine Heritage Trail 6-15-22

     Theodore Roosevelt was a passenger aboard the Narcissus on August 18, 1914. He was campaigning for the Progressive Party candidates between Lewiston, Maine, and Portland, Maine. As the volunteer project manager overseeing the restoration of the National Register of Historic Places member, Narcissus, at Seashore Trolley Museum in Kennebunkport, Maine, I have done a fair amount of research on Theodore Roosevelt and his connections to Maine throughout his life. This blog post was originally released in 2015.  Here is the updated version.

     The Seashore Trolley Museum's Theodore Roosevelt event, July 31 through August 2, 2015, is named Teddy Roosevelt Days: Celebrating the Naturalist and the Narcissus. The weekend event honors TR's passion for observing and understanding nature, his vigor for an active outdoor life, his commitment to conservation, and his connections to Maine, including the Museum's 1912 Portland-Lewiston Interurban, No. 14, Narcissus.

     Henry Wadsworth Longfellow may best be known as an iconic American figure in literature. He is honored in numerous ways throughout his hometown, Portland, Maine. I was surprised to learn that he has a Maine connection to Theodore Roosevelt, more than their shared passion for literature.  For me, these unexpected findings are like walking into a "surprise!!" moment. Being caught totally off guard. In a good way. And feeling that instant rush of exhilaration. It's pretty special for me.

     In a previous Trolley-related research project, I came across the Seashore Trolley Museum, which has artifacts connected to Henry Wadsworth Longfellow (1807-1882). The connection is through his nephew, Alexander Wadsworth Longfellow, Jr. (1854-1934). Alexander was the architect of the original way stations of the Boston Elevated Railway. Seashore Trolley Museum has one of those buildings on campus and a switching station constructed during the same time, 1901. The Northampton Street Station and Tower C switching station. 

     Now, Henry Wadsworth Longfellow connects us to Theodore Roosevelt. The bronze statue of Longfellow seated in the heart of Longfellow Square was dedicated in September 1888. Originally, State Street passed the statue on both sides. It is no longer the case. State Street, heading northwest from the Square, is where the Theodore Roosevelt International Highway (TRIH) began its long and winding trek through the northern border of the United States and even into Ontario, Canada, for a stint. That Canadian segment gives the highway its international flavor.  The TRIH comes to an end, 4,060 miles from the Longfellow statue in Portland, Maine, to a statue of Theodore Roosevelt at Park Avenue in Portland, Oregon.  The route takes one along the northern border between the U.S. and Canada.

     Growing up and living in southern Maine, I had not heard of the TRIH. However, over the years, when driving westerly on Route 302 from Portland, say, Windham, I would see various addresses with Roosevelt Trail as the destination. So, I wondered what connection there might be between TR and that road in Maine. In my research, I have acquired a few vintage postcards, found a couple of maps that refer to the TRIH, and also found a link to the 1921 map of the TRIH in the State of Montana.

Portland (ME) Sunday Telegram - March 27, 1921

Portland (ME) Sunday Telegram - March 27, 1921

Portland (ME) Sunday Telegram - March 27, 1921

30 is not the route number.

There are no specific route numbers assigned to the

TRIH. It had the name and used the various

existing route numbers in each state.

#30 starts in Portland and heads towards the Great Lakes.

Roosevelt Trail through Fryeburg, ME. No description on the back.

Postmark is not legible - PWM

..on the Theodore Roosevelt Highway between North Conway
and Bartlett. Feb. 1936 - PWM

Roosevelt Trail on Armenia Mountain, Troy, PA.

Long's Pond and Roosevelt Trail, Troy, PA - PWM

Souvenir Folder of the Roosevelt Highway and Sullivan Trail

Route - July 1953 - PWM

Foldout page from the souvenir folder, July 1953, Vol. of PWM

St-79 Standing Stone Narrows on Roosevelt Highway and

Sullivan Trail -Towanda, PA - PWM

Deer Trail - 18 miles west of Wellsboro, PA

Roosevelt Highway

Portland (ME) Sunday Telegram - March 27, 1921

This is a 1927 map - the legend shows the 

Theodore Roosevelt International Highway is #30

#30 weaves up into Ontario, then into Michigan, then back up into Ontario, where it then

enters Minnesota and heads west.

Portland (ME) Sunday Telegram - March 27, 1921

And #30 continues west to Portland, Oregon

Final Clip

Portland (ME) Sunday Telegram - March 27, 1921

     1926 Road Map, U.S.A. - This map was used by my great, great-grandfather, my great, great-grandmother, my great-grandfather, grandfather, and his younger brother when the family drove their auto from Kennebunk, Maine, to Los Angeles, CA in 1926. The promotional materials around the border are wonderful to read. The key to the map shows the Theodore Roosevelt International Highway as #39 (this does not represent any route number). I do not know if the vehicle pictured is the one used in 1926 - PWM

Frank O. Morse, Jr., Harry Lovett, Allen B. Morse (14),

Harry G. Morse (12), Frank O. Morse, Sr, and

Elizabeth J. Wells Morse c 1919 - PWM

The legend has 39 listed as the

Theodore Roosevelt International Highway -

Portland, Maine to Portland, Oregon

Follow 39 from Portland, Maine heading to Niagara Falls, NY - PWM

Follow 39 into Ontario

Follow 39 back into the U.S.A. - PWM

39 travels north through Michigan and back into Ontario.

39 then runs west and enters Minnesota at Duluth.

39 runs west through Minnesota and into North Dakota.

As 39 continues west through ND, it is north of TR's ranch

 and now Theodore Roosevelt National Park near Medora, ND

39 continues west through Montana and into Idaho.

Follow 39 to Portland, Oregon. At the end of the

Theodore Roosevelt International Highway - 4,060 miles
from Portland, Maine

I enjoyed reading about the TRIH in the book,
Moose Crossing, by Max J. Skidmore.

Hamilton Books, 2007.

~~~~~~~~~~~~~~~

Click Here: For the list of links to Theodore Roosevelt Maine Heritage Trail Posts in Easy Order to View

We continue the restoration work on the 1912 Narcissus, the only surviving high-speed, luxury interurban coach of the Portland-Lewiston Interurban. 

Click Here: Narcissus Restoration-Related Posts

More than a century old, the stately "Elegant Ride," Narcissus, is a gem.  This shimmering precious stone of Maine transportation history is brilliantly resplendent as it emanates so many elements of history, including time, places, people, and events, that it was coupled to, that when just a smattering of its seemingly innumerable stories are shared, the contents first captivate, fascinate, then generate interest to learn more 🙋. The majestic Narcissus is listed in the National Register of Historic Places.

Please consider joining the epic journey to complete the Narcissus Project by donating today!

Click Here: Donation Options

The restoration of this majestic icon of Maine's electric railway history is but one in a series of captivating stories containing an abundance of incredible coalition narratives.

Click Here: History-Related Posts - Narcissus and Portland-Lewiston Interurban

     The Narcissus is featured in the national Gold Award-winning novel, Teddy Roosevelt, Millie, and the Elegant Ride. The "Elegant Ride" is the Narcissus. Theodore Roosevelt was a passenger on the Narcissus on August 18, 1914, between Lewiston and Portland, Maine, while campaigning for the Progressive Party candidates.

Click Here: Bookstores and Businesses promoting the Narcissus Project

Independent book publisher Phil Morse, holding

Gold Book Award Winner plaque for

 Middle Reader category for The Eric

Hoffer Book Award. Congratulations to

award-winning Maine author,

Jean M. Flahive

Theodore Roosevelt - Master Mason

Courtesy Library of Congress

Theodore Roosevelt - Freemason

Update: 07-17-2026

New in 2022 - First Post for the Theodore Roosevelt Maine Heritage Trail June 16, 2022

      First Look at Logo - "My Debt To Maine" - Logo - Theodore Roosevelt Maine Heritage Trail 6-15-22

THEODORE ROOSEVELT (1858-1919)

Twenty-sixth President (1901-1909)

MASONIC RECORD

A postcard with no handwritten message -
Collection of PWM

    Initiated: January 2, 1901, Matinecock Lodge No. 806, Oyster Bay, New York. Brother and President Roosevelt visited the Grand Lodge of Pennsylvania on November 5, 1902, for the Celebration of the Sesquicentennial of Brother George Washington's Initiation into Freemasonry. Governor of New York, 1899-1901. Brother and President Roosevelt issued an Executive Order, dated October 17, 1901, changing the name of the "Executive Mansion" to the "White House".

I heard that it was Colonel Roosevelt's gardener at Sagamore Hill, TR's home in Oyster Bay, NY, who nominated TR to become a Mason.

I read a post on The Roosevelt Dynasty: Family, Fitness, & Faith group on Facebook that includes the photo below. The post states, As a child, TR's social life was centered around women. His mother, older sister Bamie, younger sister Conie, Aunt Anna (his teacher through his childhood), and even Edith, later First Lady, dominated his social group.

It wasn't until he went to Harvard, all men at the time, and then North Dakota that his social group became mostly male. His time with men out West changed him both physically and mentally.

He had a few male friends growing up. Brother Elliott was the closest friend. As a reen, TR spent the summers in Oyster Bay. He developed a friendship with William L. Swan that would persist for decades. Swan was influential in the formation of Marinecock Masonic Lodge No. 806 in 1893. Later, he would persuade his boyhood friend Theodore Roosevelt to become a Mason.

Photo (below) of TR(left) in 1907 at a Masonic function where a cornerstone is being laid.

Theodore Roosevelt and the Narcissus story in 2014, Vol. 40, No. 3,
Fall issue of The Maine Mason Collection of PWM

Click here to open the post on donating to the Narcissus Project

The Theodore Roosevelt story in the 2022, Vol. 48, No. 2,
Spring issue of The Maine Mason - Collection of PWM

Freemason Novelty Note - Darkened - This is
a beautifully colored and detailed note on the front and the reverse side is
equally detailed and titled Steps of Freemasonry.
Go to www.noveltynotes.com

~~~~~~~~~~~~~~~

Click Here: For the list of links to Theodore Roosevelt Maine Heritage Trail Posts in Easy Order to View

We continue the restoration work on the 1912 Narcissus, the only surviving high-speed, luxury interurban coach of the Portland-Lewiston Interurban. 

Click Here: Narcissus Restoration-Related Posts

More than a century old, the stately "Elegant Ride," Narcissus, is a gem.  This shimmering precious stone of Maine transportation history is brilliantly resplendent as it emanates so many elements of history, including time, places, people, and events, that it was coupled to, that when just a smattering of its seemingly innumerable stories are shared, the contents first captivate, fascinate, then generate interest to learn more 🙋. The majestic Narcissus is listed in the National Register of Historic Places.

Please consider joining the epic journey to complete the Narcissus Project by donating today!

Click Here: Donation Options

The restoration of this majestic icon of Maine's electric railway history is but one in a series of captivating stories containing an abundance of incredible coalition narratives.

Click Here: History-Related Posts - Narcissus and Portland-Lewiston Interurban

     The Narcissus is featured in the national Gold Award-winning novel, Teddy Roosevelt, Millie, and the Elegant Ride. The "Elegant Ride" is the Narcissus. Theodore Roosevelt was a passenger on the Narcissus on August 18, 1914, between Lewiston and Portland, Maine, while campaigning for the Progressive Party candidates.

Click Here: Bookstores and Businesses promoting the Narcissus Project

Independent book publisher Phil Morse, holding

Gold Book Award Winner plaque for

 Middle Reader category for The Eric

Hoffer Book Award. Congratulations to

award-winning Maine author,

Jean M. Flahive

Two Accomplished Writers and a National Park Service Ranger from Sagamore Hill NHS will Speak at Theodore Roosevelt Event this Summer at Trolley Museum

The Seashore Trolley Museum will present a new weekend event beginning this summer, on July 31, 2015. The weekend event titled Theodore Roosevelt: Naturalist, Nature, and the Narcissus honors our 26th President, Theodore Roosevelt, and his conservation efforts, while celebrating his connection to Seashore's own 1912 Portland-Lewiston Interurban No. 14, Narcissus. Proceeds benefit the Narcissus restoration project. This weekend includes engaging, enlightening, challenging, and fun activities and programs for all.  This event embraces Theodore Roosevelt's passion for observing and understanding nature, his vigor for an active outdoor life, his commitment to conservation, and his connections to Maine. More details about the event activities will be in future posts. Here are the featured speakers for the exciting weekend.

Chip Bishop

Chip Bishop will be speaking about his new book, Quentin & Flora - A Roosevelt and a Vanderbilt in Love during the Great War. 

Chip is a member of the board of directors of the Biographers International Organization, on the Advisory Board of the Theodore Roosevelt Association, and on the executive committee of its New England chapter. He is the great-grandnephew of Joseph Bucklin Bishop, Theodore Roosevelt’s authorized biographer, who was profiled in his first book, The Lion and the Journalist – The Unlikely Friendship of Theodore Roosevelt and Joseph Bucklin Bishop. Chip has now started a biography of Elliott Roosevelt, TR's younger brother and the father of Eleanor Roosevelt. Mr. Bishop will be signing and selling his books at the event on Friday, July 31, at 3pm.

                 

TR's brother Elliott is Eleanor Roosevelt's father.

TR would become the 26th President of the United States.

Eleanor would marry Franklin D. Roosevelt, a distant cousin,

who later became the 32nd President of the United States.

Andrew Vietze

The former Managing Editor of Down East: The Magazine of Maine, Andrew Vietze, is a bestselling author. The critically acclaimed Becoming Teddy Roosevelt (Down East, 2010) won a silver medal at the Independent Publisher Book Awards in New York, was a ForeWord Book of the Year Finalist, and was the inspiration for Coastal Maine BotanicalGarden's new program for middle schoolers, the Lunder New Naturalists, which is now part of the curriculum at 20 Maine schools and involves more than 600 students. The book speaks about Theodore Roosevelt and the Maine Woods with legendary Maine guide William Sewall. He was a sickly, asthmatic city boy. When he emerged several trips later, he was a robust, confident outdoorsman—the kind of man who could be president. This book describes the lifelong friendship between the twenty-sixth president and the lumberman from Island Falls. Explores how that bond changed Roosevelt (and the nation) and why it matters today. Andrew will be signing and selling his books at the event on Saturday and Sunday, August 1st and 2nd.

William Wingate Sewall, Wilmot Dow, and Theodore Roosevelt,

with the snowshoes in Maine, c February 1879

Houghton Library, Harvard University

While an undergraduate student at Harvard University, Theodore Roosevelt visited Island Falls, Maine, on three occasions between 1878 and 1879. TR would stay at Sewall's home, and William Sewall and William's nephew, Wilmot Dow,  would be TR's guides. 

May 31, 2026, Joe Banavige released this wonderful American 250 Tribute to william W. "Bill" Sewall, TR's Maine guide (along with Wilmot Dow, Bill's nephew). Click here to see Joe's Substack post.

R.Joshua Reyes

Sagamore Hill, Oyster Bay, NY
Collection of PWM

Joshua Reyes  

Joshua Reyes is a National Park Service Park Ranger at Sagamore Hill National Historic Site, the Theodore Roosevelt family home in Oyster Bay, NY. Josh has worked for the National Park Service for twelve years. He is the volunteer coordinator at Sagamore Hill and will speak about TR's family. Life at Sagamore Hill with insight into the three-year renovation of the site. The anticipated reopening date for Sagamore Hill is July 12, 2015. The National Park Service Centennial will be celebrated in August 2016, and to kick off the year approaching the centennial, the NPS has introduced the new

Find Your Park program.

Josh will be speaking to guests on Friday night, July 31, Saturday, August 1, and Sunday, August 2.

Theodore Roosevelt in the dining room of his beloved home,
Sagamore Hill ca 1894,  TRC R500.R67-002 

Houghton Library, Harvard University

~~~~~~~~~~~~~~~

Click Here: For the list of links to Theodore Roosevelt Maine Heritage Trail Posts in Easy Order to View

We continue the restoration work on the 1912 Narcissus, the only surviving high-speed, luxury interurban coach of the Portland-Lewiston Interurban. 

Click Here: Narcissus Restoration-Related Posts

More than a century old, the stately "Elegant Ride," Narcissus, is a gem.  This shimmering precious stone of Maine transportation history is brilliantly resplendent as it emanates so many elements of history, including time, places, people, and events, that it was coupled to, that when just a smattering of its seemingly innumerable stories are shared, the contents first captivate, fascinate, then generate interest to learn more 🙋. The majestic Narcissus is listed in the National Register of Historic Places.

Please consider joining the epic journey to complete the Narcissus Project by donating today!

Click Here: Donation Options

The restoration of this majestic icon of Maine's electric railway history is but one in a series of captivating stories containing an abundance of incredible coalition narratives.

Click Here: History-Related Posts - Narcissus and Portland-Lewiston Interurban

     The Narcissus is featured in the national Gold Award-winning novel, Teddy Roosevelt, Millie, and the Elegant Ride. The "Elegant Ride" is the Narcissus. Theodore Roosevelt was a passenger on the Narcissus on August 18, 1914, between Lewiston and Portland, Maine, while campaigning for the Progressive Party candidates.

Click Here: Bookstores and Businesses promoting the Narcissus Project

Independent book publisher Phil Morse, holding

Gold Book Award Winner plaque for

 Middle Reader category for The Eric

Hoffer Book Award. Congratulations to

award-winning Maine author,

Jean M. Flahive