Portland, Maine: Black History Walking Tour & Stories

Summary

Portland’s cobblestones hold Black voices lost in plain sight

You’ll walk Portland’s oldest streets with Dugan, hearing stories of Black Mainers who shaped the city’s soul—from secret signals in barbershops to bold choices on the waterfront. Expect laughter, pauses for thought, and moments when history feels suddenly close. It’s not just facts—it’s voices you can almost hear under your feet.

What’s the experience like?

We met Dugan outside a bakery—he waved, called us over by name, and handed out little slips with a map. “We’ll start here,” he said, pointing at the crooked granite underfoot. I hadn’t really noticed those stones before—he said Frederick Douglass walked this same stretch. There was a smell of coffee drifting from somewhere nearby, and for a second I just watched a dog tugging its owner down the street. Dugan grinned and told us about barbershops that used to line these blocks, where abolitionists whispered secrets for the Underground Railroad. He even tried to show us how people would signal each other—my attempt at the gesture made him laugh. I liked that he didn’t rush; he let us linger by an old storefront window, just looking in silence.

There’s something about hearing Black history in Portland while you’re actually standing there—like when we paused by the waterfront and Dugan pointed out where Black sailors loaded ships centuries ago. The wind off the harbor was sharp that day (should’ve brought gloves), but it kept me awake to every word. He told us about a journalist who left America for Africa—his voice got quiet then—and I caught myself wondering what it must have felt like to make that choice. We climbed a set of 17 steps (not as bad as I feared) up to the old meeting house, where he showed us photos of community leaders who changed laws most people never hear about.

I didn’t expect to feel so much—maybe it was the way Dugan shared stories like he’d dug them up himself (which he pretty much did). At one point we stopped near an old church and he talked about racial passing in 19th-century Maine; someone in our group asked if things had really changed, and nobody answered for a minute. That silence stuck with me more than any fact or date.

Step-by-step itinerary

Day 1 — Black History Guided Walking Tour in Portland

• Meet guide Dugan Murphy
• Trace Black Mainers' achievements
• Discover pre-slavery Black history
• Learn about 19th-century activist
• Hear racial passing history
• Explore Black leaders at waterfront
• Honor Black journalist's legacy
• Discover Black maritime skills
• Marvel at antebellum Black power
• Visit WWII Black social scene
• Walk Old Port's historic Black area
• Learn young Black lawyer's story
• Find Underground Railroad helpers
• See tight-knit community achievements
• Understand Black role in maritime economy
• Visit civil rights movement heart
• Hear Black minister's constitutional role

Top questions

How long is the Portland Black History walking tour?

The tour lasts around 2 hours and covers about 1.5 miles through Portland’s historic areas.

Who leads this Black History tour in Portland?

The tour is led by Dugan Murphy, a local historian known for his engaging storytelling.

Is this walking tour wheelchair accessible?

Yes, all areas and surfaces are wheelchair accessible, though there is one staircase of 17 steps included on the route.

Are children or strollers allowed on this tour?

Yes, infants and small children can ride in a pram or stroller during the tour.

Does this tour include any donations or community support?

A portion of your ticket goes toward restoring the Abyssinian Meeting House, America’s third-oldest standing Black church.

Will I learn about Underground Railroad history on this tour?

Yes, you’ll hear stories about abolitionists and sites connected to the Underground Railroad in Portland.

What should I wear or bring for this day trip in Portland?

Wear comfortable shoes for walking; weather can be cool near the waterfront so bring layers or gloves if needed.

What’s included

Your day includes two hours of guided narration by Dugan Murphy along a 1.5-mile route through Portland’s historic districts, plus a 10% discount on water tours with Portland Paddle (details come with confirmation). Part of your ticket also supports restoration efforts at the Abyssinian Meeting House—a living piece of Black history you’ll see along the way.