Robert Sylvain hosts a Jane’s Walk for May 2, 2026 starting at 2pm. Meet at the top of Chestnut Street at the corner of Congress Street by city hall and we’ll walk down Chestnut into what used to be the briny waters of Back Cove.
— Reference Maps —
Bayside has always been a neighborhood in flux. Join us for a stroll down Chestnut Street and we’ll see just how much has changed—starting with the fact that most of what we’re walking on used to be underwater!
A map held by the Maine Historical Society traces five different shorelines of Back Cove—1837, 1870, 1900, 1940, and 2003. Each one marks another round of fill, another push of the water back. In 1837, the cove reached all the way up to Oxford Street, just a few blocks from where we start. By 1870, the railroads had begun their work. By 1900, whole neighborhoods were being built on what had been mudflats. The process didn’t stop until well into the 20th century.
We’ll walk down Chestnut Street from Congress to Marginal Way—about half a mile—using that map as our guide. We’ll stop along the way to identify which layer of fill we’re standing on, look at how the street grid bends and shifts where the old shoreline used to run, and talk about who made these decisions and why. We’ll look at what the neighborhood became as a result, and what traces of the original landscape are still visible if you know where to look.
This walk is an opportunity to reflect on the long arc of urban planning decisions that made Bayside what it is today—and to sit with some questions that don’t have easy answers. What do we gain when we reshape a landscape, and what do we lose? How do cities balance growth with what’s already there? And with sea levels rising and Back Cove appearing on climate vulnerability maps, what might the next chapter of this shoreline’s story look like?
You don’t need to know anything about history or urban planning to enjoy this walk. You just need to be the kind of person who wonders what’s underneath things. Bring comfortable footwear, drinking water if you like, and questions we can try to answer together.