Portland Maine: Walking Tour of Untold Local Histories

Summary

Walk Portland’s Old Port, hear hidden voices, connect with Maine’s past

You’ll walk Portland’s Old Port with a local guide who shares surprising stories left out of most tours—think unsung heroes, Indigenous leaders, and resilient communities. Expect laughter, quiet moments by Casco Bay, and real conversations about Maine’s past—and future. Includes a donation supporting historic restoration that connects every step to something bigger.

What’s the experience like?

“You won’t find this story on any plaque,” Dugan said as we paused near a brick alley that honestly I’d never have noticed by myself. The air smelled faintly of salt and coffee—someone nearby was roasting beans, or maybe just burning toast. We were only ten minutes into this Portland walking tour and already I’d learned more about the city than in my last three visits combined. Dugan grew up here—he talks about the streets like they’re old friends, and he doesn’t shy away from the messy parts either. That felt honest.

I liked how he pointed out the little details: the way certain Victorian buildings lean ever so slightly, or how you can still spot marks from old ship ropes along Commercial Street if you squint. There was this moment when we stopped in front of a building I’d passed before but never really saw—turns out it housed someone whose name should be everywhere but isn’t. Dugan told us about a woman who lived as her true self a century ago; I got goosebumps hearing how she changed lives around her, quietly but powerfully. It made me wonder what else I’ve missed just walking around cities.

The route was easy enough (though there are some hills—my legs reminded me later), and we drifted through Old Port toward Casco Bay, passing locals who nodded at Dugan like he’s part of the landscape. He wove in stories of Indigenous Wabanaki leaders and Black Mainers, folks you don’t usually hear about on tours like this. There was laughter too—especially when someone tried to pronounce “Abyssinian” and totally flubbed it (not naming names). Honestly, I still think about that view down to the waterfront at dusk; something about the light bouncing off wet cobblestones sticks with me.

This wasn’t just another day trip in Portland—it felt more like being invited into an ongoing conversation about what Maine is and could be. The tour included a donation to restore America’s third-oldest Black church, which felt right after hearing those stories. If you want polished monuments and tidy answers, maybe look elsewhere—but if you want to walk Portland with someone who cares deeply about its people (all its people), well…you’ll probably remember this one.

Step-by-step itinerary

Day 1 — Explore Portland's hidden histories

• Meet guide Dugan Murphy
• Walk Downtown District landmarks
• Learn about unsung local heroes
• Meet historic woman who lived authentically
• Appreciate Victorian architecture stories
• Discover Indigenous community resilience
• Uncover stories behind Portland's largest monument
• See oldest downtown building and story
• Follow Old Port hidden histories
• Explore history of famous Portland son
• Learn about forgotten history-makers
• Discover 19th-century maritime relationships
• Stroll waterfront along Commercial Street
• Understand global impact of maritime history
• See working waterfront and female figures
• Hear effects of federal policies on port

Top questions

How long is the Portland hidden histories walking tour?

The guided walking tour lasts approximately two hours over a 1.5-mile route.

Is the Portland walking tour wheelchair accessible?

Yes, all areas and surfaces are wheelchair accessible including transportation options nearby.

Who leads the hidden histories walking tour in Portland?

The tour is led by Dugan Murphy, a locally-raised guide and owner rated top on TripAdvisor.

Does this Portland day trip include any donations or community support?

Yes, your booking includes a donation toward restoring the Abyssinian Meeting House.

Are pets allowed on this Portland Maine walking tour?

No pets are allowed unless they are medically required service animals.

What neighborhoods does the walking tour cover?

The route covers Downtown District and Old Port in Portland, Maine.

Will I hear stories about Indigenous communities on this tour?

Yes, stories of Indigenous Wabanaki leaders and their resilience are included naturally throughout the walk.

Is lunch or food included during the walking tour?

No meals are included during this two-hour experience.

What’s included

Your afternoon includes two hours of fully narrated guiding through downtown Portland and Old Port with Dugan Murphy, plus 10% off water tours with Portland Paddle (instructions come after booking) and a donation toward restoring the historic Abyssinian Meeting House—all without rushing or missing those quieter moments that make it feel real.