Walk Commercial today and you’re standing on Portland’s missing waterfront.
You’ll pass oyster bars, nautical themed shops, and tourists gripping chowder bread bowls like lifelines. Under the asphalt is another Portland entirely.
Before parking lots and cruise‑ships, the tide curled into a pocket called Clay Cove between India and Franklin. Clay Cove was the heart of Portland’s shipbuilding and maritime trade. Shipwrights hammered white‑pine ribs, stacked molasses casks, as Fore Street curved around the water’s edge like a spine. A creek ran all the way up to Middle Street, so central the town arched a bridge over it. Portland wasn’t built next to the cove; it rose out of it.
On October 18, 1775: Loyalist Captain Henry Mowatt’s fleet parked offshore and demanded obedience and punishment for the seizure of British vessels. Portland stalled. The Royal Navy answered with hot shots. In nine hours four hundred wooden buildings went up like tinder, masts popping like kindling. Clay Cove’s boatyards became a bonfire you could smell from Cape Elizabeth.
Here’s the twist: the fire cleared the slate. The town rebuilt with brick, straighter streets, and bigger wharves that could handle the booming post‑Revolution grain and lumber trades. The blaze that was meant to break Portland ended up hardening it.
By the mid‑1850’s steam and rail replaced canvas and tide. Crews dumped thousands of cubic yards into Clay Cove, spiked rails, and slapped on a new name—Commercial Street. Warehouses replaced wharves; the Grand Trunk depot rose next, followed by cookie‑cutter hotels and a cruise‑ship dock. Not exactly our proudest architectural flex.
The harbor that launched Portland now hides under rental cars and conference name tags.
Today, when you stand at the corner of India and Commercial, take a moment to pause. Look down at the pavement beneath your feet, where layers of history lie buried. Beneath the concrete of Commercial Street is a waterfront that once hummed with life, where ships were built, goods traded, and Portland’s identity was forged.
So next happy hour, when you flick an empty oyster shell into the bucket, toast the shipwrights who built fortunes from mud, the families who rose after the fire, and the planners bold enough to swap tide for track. Clay Cove is buried, but it’s still holding the city up.
What do you think Portland’s waterfront would be like if Clay Cove hadn’t been filled in? |
I’m in South Florida right now. The weather’s perfect. Palm trees lean just right. The Cuban sandwiches are the real deal.
And still, Portland’s in my chest like a heartbeat I can’t shake.
I didn’t expect to miss it this fast. But I do.
Down here, nothing’s older than the ‘40s. Everything feels like it came off an assembly line. I miss homes with creaky floorboards, stained glass transoms, plaster walls that breathe. In Portland, even the buildings feel like they’ve lived a little. Scarred and beautiful.
I miss food that means something. Portland chefs don’t perform, they cook like they are feeding family.
I miss walking. Not hiking. Not mall-lapping. Just walking through a city built for it. From the West End to Munjoy Hill, from a quiet bench on the Prom to the back corner of Architectural Salvage ( RIP, Alice if you are reading this call me ❤️ ) . Every block back home has a story.
Here, walking without a dog or leggings gets you looks.
And the antique stores? Forget it. I haven’t seen a tramp art box since I got here. In Portland, a good junk shop smells like cedar and dust. Here, everything’s staged and spotless. Like it’s waiting for a catalog shoot, not a life.
But mostly, I miss the people.
The quiet obsessives. The ones who care about the small stuff. Who remember your name, your drink order, and that dumb thing you said two Thursdays ago—even though they said they wouldn’t judge you for it and that’s who I want to be around.
I’ll be back in a week. But being away reminded me: Portland’s not always easy. It’s not always convenient. But it’s real.
And once it’s in you, it stays there.
What do you miss when you’re away? Hit Reply and Let me know.
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🐕 Interested? Check them out here
Cove Run Tuesday @ Back Cove | 6am | Free
Kids: All About Box Turtles @ Children’s Museum | 10am | 🎟️ Museum Ticket
Talk: Space on Earth Panel @ Space | 7pm | 🎟️ Advanced
Best Worst Trivia Night @ Another Round | 6:30pm | Free
Deering Oaks Farmers Market- Half Vender, Wednesday’s @ Deering Oaks Park | 7am | Free
Portland Stitch Club @ Novel | 6pm | Free
Sunrise Yoga and Writing @ Mechanics Hall | 7am | 🎟️ $15
Film: Ponyo ( Japanese with English Subs) @ PMA | 12pm| 🎟️ $10
Film: Ponyo ( English Dub) @ PMA | 3pm | 🎟️ $10
Dance Party: Hot off the Press w/ DJ Ben Spalding @ Novel | 8pm | 🎟️ $5
Film: My Sweet Land @ Space | 6:30pm | 🎟️ $10
Music: Pete Rock w/ Damn B @ Oxbow Brewing | 7pm | 🎟️ $45
Sips and Stories w/ The Lucky Fox Bookshop and Back Cove Books @ Five of Clubs | 6pm | Free
Free Art Museum Friday @ The Portland Museum of Art | 4pm | Free
Start of Maine Seaweed Week | Various Times | Various Locations
Palaver Strings Concert: But There is This @ Mechanic’s Hall | 7pm | 🎟️ $25
Phish Tribute Concert @ Bayside Bowl | 8pm | 🎟️ $12
April Drag Storytime with Portland Ovation @ Portland Public Library | 11am | Free
Deering Oaks Farmers Market @ Deering Oaks Park | 7am | Free
Westbrook SeaFest @ RiverBank Park | 2pm | Free
Portland Annual City Street Clean Up Project (Half Jog/ Half Trash Pick up) @ Austin Street Brewery | 11am | Free
Portland 2nd Annual Chowder Fest @ Definitive Brewing | 12pm | 🎟️ $30
Hearts of Pine Watch Party @ Rising Tide Brewing | 3:30pm | Free
Nick Swardson: Toilet Head @ State Theatre | 7pm | 🎟️ $35
6th annual: Taco and Tequila Bar Crawl @ Fore St Pub | 8pm | 🎟️ $42
Northeast Sports Card Expo @ Portland Expo Building | 4pm | 🎟️ $12
Coffee Run @ Forage Market | 9am | Free
Salty Water Pasta Popup @ Coveside Coffee | 5pm | 🎟️
Seconds Bakery Popup @ Lay Day Roasters | 9am | Free
Opposites Attract Market @ Rising Tide Brewing | 12pm | Free
2025 Portland 10 Miler @ Edward Payson Park | 8am | 🎟️ $80
Music: Revenge Body @ SilverFish | 7pm | 🎟️ $10
Music: BucketHead @ State Theatre | 8pm | 🎟️ $35
Northeast Sports Card Expo @ Portland Expo Building | 4pm | 🎟️ $12
Art: The Creating House @ Novel | 7pm | Free
Raul Perez Wine Dinner @ Chaval | 6pm | 🎟️ $153
Nimki Restaurant Popup @ Bar Futo | 5pm | 🎟️
Game Night @ Another Round | 5:30 | Free
Architalx 2025 Lecture Series: Laura Stein @ Aura | 6pm | 🎟️ $ 17.50
Until next week,
— Jake
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