The Portland Logbook #7

This Week in Portland Maine

Jake Newman
March 18, 2025

Portland's Forgotten Battlefield: The War That Shaped Casco Bay

Portland looks good these days. Cobblestone streets, lobster rolls, overpriced craft cocktails. But this city wasn’t always a postcard. It was burned, abandoned, fought over, and left for dead more than once. The Old Port you know now was a battlefield, a place where survival meant muskets, fire, and running like hell. Beneath your feet, the ghosts of that past still linger. You just have to know where to look.

The Battle for Casco Bay

In the summer of 1676, during the throes of King Philip's War, tensions between English settlers and the Wabanaki Confederacy reached a boiling point. The English had been expanding their settlements into Wabanaki territories, disrupting traditional hunting grounds and fishing waters. This encroachment, coupled with the broader conflict engulfing New England, set the stage for a fierce confrontation.

The Wabanaki, skilled in guerrilla tactics and intimately familiar with the land, launched a series of coordinated attacks on English settlements along the Maine coast. They aimed to halt the tide of colonial expansion and reclaim their ancestral lands. The settlers, unprepared for the ferocity and strategic prowess of the Wabanaki, found themselves on the defensive.

One notable incident occurred in September 1676, when Wabanaki warriors attacked the settlement at Falmouth (present-day Portland). They burned homes, destroyed crops, and killed or captured dozens of settlers. The survivors fled to fortified garrisons or escaped by sea, leaving the area largely abandoned.

The Aftermath and Legacy

The conflict led to a temporary withdrawal of English settlers from the Casco Bay region. It wasn't until the signing of the Treaty of Casco in 1678 that a fragile peace was established, allowing settlers to return under the condition that they respect Wabanaki land rights and trade practices.

This turbulent period is a testament to the resilience of both the indigenous populations and the settlers. The Wabanaki's resistance highlighted their determination to protect their homeland, while the settlers' eventual return demonstrated their commitment to establishing new lives in a challenging environment.

Why This Still Matters

Portland's rich history is woven into its streets and shorelines. The events of 1676 serve as a reminder of the complex relationships and struggles that have shaped the region. Acknowledging this past enriches our understanding of the city's identity and honors the narratives of those who came before.

As you stroll along the waterfront, consider the layers of history beneath your feet. The bustling markets and lively docks stand atop a land once fiercely contested, where cultures clashed, and communities were forged in the fires of conflict. But history isn't just something that sits behind glass in a museum. It's alive, carried forward in the hands of those who honor the traditions of their ancestors.

If you want to see that legacy in action, seek out the work of Passamaquoddy basketmaker Jeremy Frey. His weaves are mind-bending, impossibly precise, like something conjured rather than crafted. They aren’t just art. They’re history made tangible, a throughline from past to present, a testament to Wabanaki resilience and craftsmanship. You can find a few at the Portland Museum of Art. Go. Stand there. Let it sink in.

📢 What Should We Obsess Over Next?

Portland’s got layers, some soaked in history, others dripping in butter. What should we go deeper on?

The Results are in and the Table is Booked

Last week i asked you to vote which of the 3 places that i was recommended to go to next by The Wayside tavern team.

📍 Smalls (17) 🟨🟨🟨🟨⬜️⬜️

🌶️ Crispy Gai (24) 🟩🟩🟩🟩🟩🟩

🌮 Taco Trio (14) 🟨🟨🟨⬜️⬜️⬜️

🐾 Adoptable Buddies of the Week! 🐾

🐱 Tangerine – A shy but sweet black tabby looking for a patient home. As a member of the Tiny Tiger Club, she’s still learning to trust people and will need time to adjust. She does best with a confident feline friend and a calm space—no young kids, just quiet companionship and gentle encouragement.

🐹 Hippo – A chatty, fluffy guinea pig with a love for floor-time zoomies and fresh greens. He’s looking for a guinea pig-savvy home where he can feel safe and maybe even meet a piggy pal. If you’re ready to earn his trust, he’ll be the happiest little buddy.

No dogs, birds, or bunnies this week! If you know a local rescue I should feature, let me know.

🐕 Interested? Check them out here