The original Pine Tree Trail sign found by Robbie McKay and Nate Nipula in Molunkus. Credit: Alexander MacDougall / Houlton Pioneer Times

Hard Telling Not Knowing each week tries to answer your burning questions about why things are the way they are in Maine — specifically about Maine culture and history, both long ago and recent, large and small, important and silly. Send your questions to

This week’s question originally came from a guy in the township of Molunkus, who found a rusty old road sign on his property and ended up uncovering a nearly 85-year-long mystery.

Why does no one know about Maine’s 500-mile Pine Tree Trail?

Since the late 19th century, Maine has been a vacation destination for people from all over the world — but it only officially became Vacationland in 1936, when the nickname was added to Maine’s license plates, and began appearing on official state tourism bureau material.

To capitalize on Maine’s new branding, the Maine Legislature in 1937 passed An Act to Designate a Route from Portland to Fort Kent as the Pine Tree Trail — an automobile trail that lawmakers hoped would compel travelers to explore as much of the state as possible, especially the inland areas, away from the popular coast.

The act was passed. Road signs were made up. Maps were printed. And then, after World War II, Maine’s state highways were modernized, new roads were built, the interstate highway began to creep up the coast, and the Pine Tree Trail was all but forgotten for the next seven decades.

Fast forward 75 years. In 2012, Nathan Nipula, a resident of the Aroostook County township of Molunkus, found a rusty old road sign discarded amid a pile of dirt and rocks on his property. He didn’t know what “Pine Tree Trail” meant, but he brushed it off, tossed it in storage and didn’t look at it again for another seven years.

In 2019, Nipula and his fiancee, Roberta McKay, pulled the sign back out and decided to try to figure out what the Pine Tree Trail was. Their search led them to Maine’s then-Secretary of State Matt Dunlap, who did a little research and quickly discovered the sign’s origins — and that the 1937 act that created the trail was very much still on the books.

Over the past three years, Dunlap, Nipula, McKay and state officials and legislators have been working to recreate the Pine Tree Trail, including raising money for 100 road signs to be installed along the trail’s length, as well as future events, maps, travel guides and other efforts. A website,, was launched earlier this year.

“In the day, it was Maine’s version of Route 66. Maybe it can be again,” Dunlap said, referring to the famous western U.S. route that became an iconic road trip destination in the 1930s, 40s and 50s, before its decline in the 1960s.

The “new” route mostly follows routes 100, 2 and 1, north from Portland, through Augusta and Waterville to Bangor, and then north through Houlton, Mars Hill, Presque Isle and Van Buren before ending in Fort Kent — or starting in Fort Kent, if you’re coming from the other direction. There are two alternate routes at two points in the trail — one where Route 2 and Route 2A split off between Macwahoc and Houlton, and again when Route 1 and Route 1A split off between Mars Hill and Van Buren.

A number of the new road signs have already been installed in Aroostook County, and all the signs will be installed statewide by the end of October. Businesses and organizations can also sponsor a Maine Department of Transportation-approved sign, with several businesses in Aroostook and Penobscot counties already signed up to sponsor.

“From a tourism perspective, this checks all the boxes of our initiatives to spread visitors around the state, inspire the exploration of more places, and work with Maine communities to expand and create more diverse and robust tourism product offerings for visitors and residents alike,” said Hannah Collins, deputy director of the Maine Office of Tourism.

Emily Burnham is a Maine native and proud Bangorian, covering business, the arts, restaurants and the culture and history of the Bangor region.