Roosevelt Island Main Street
Main Street Canyon, Roosevelt Island

The facts are in: Roosevelt Island’s Main Street is messed up.


Roosevelt Island’s Main Street problem may never be perfectly solvable, but it can get better. Meanwhile, facts matter.

Reporting by David Stone

Roosevelt Island Daily News

Roosevelt Island’s Main Street problem is self-created isolation, a canyon that defies life on a river. It was not designed for cars and trucks, but they crowd the lanes nowadays, anyway.

Roosevelt Island’s Main Street Flipped History

You won’t notice, right away, but Roosevelt Island‘s Main Street is, as my brother Gary would say, “back asswards.”

My brothers all have a gift for the vernacular, colorful ways of making their points. Simple descriptions won’t do, and they shouldn’t.

You take a quick look at Main Street, and things stack up like you’d expect. You walk the Main Street Canyon. You pass front entrances like anyone expects, but look again. That’s not always what you find here.

Rear doors and walls are normally hidden in alleys, hard to reach, wasted spaces. But not on Roosevelt Island, because in the most significant places, the opposite is true.

Most of us walk by the lineup of half-empty storefronts a lot of times before realizing that, when you pass the Chapel of the Good Shepherd, you’re looking at its back end. Back asswards, get it?

The rustic front entrance isn’t visible from the street.

Main Street, in the center of town, features the back end of the Chapel of the Good Shepherd.

When you look with a clear eye, you find no obvious entrance on Main Street. You also can’t see the front from the river because it’s curiously obscured by a string of low slung apartments.

One of Main Street’s intractable problems begins there. When building started off for the new community, planners somehow decided to hide the most attractive features.

But that doesn’t end with historic venues. Ed Logue’s vision for sweeping river views was likewise obliterated. Looking for a reason? Nothing clear is on the record.

Walk all the way around to see the country church facade that welcomed indigents. But the almshouse workers are gone, and we’ve still got a backward church

Roosevelt Island’s Main Street problem extends…

Walk a little farther south to Blackwell House. The pattern comes up again. 

Blackwell House, winter afternoon
Blackwell House, seemingly always under construction, but finally reopened after two decades vacant.

A small, inviting porch shaded by a tall tree. There’s even an historic marker. But don’t be misled. You’re gazing at the back door.

Swing around to the other side and find a broad, welcoming front porch, sweetly appropriate for its day. Settlers built Blackwell House on a natural knoll facing the river. On the far shore, Ravenswood, bucolic and destined to become New York City’s first suburb.

Yet, Main Street’s inexplicably routed past its back door.

About the WIRE Buildings

Why do the original Roosevelt Island housing complexes – Westview, Island House, Rivercross and Eastwood – defy the notion that they’re on an island?

Founding designer Edward Logue envisioned sweeping river views, but that waited for decades until Southtown caught on.

All four buildings shun the water and the skyline, crowding instead into a narrow, sun-deprived canyon.

Worse yet, lurking behind them are baffling pathways and courts as well as a row of what look like afterthought mother-in-law apartments, all of which obstruct river access and views.

Roosevelt Island’s Main Street problem happened because the state mismanaged, building an inexplicable canyon.

Facing in. Away from the water.

Roosevelt Island’s Main Street problem: Not just a lack of imagination…

My first impression of the Main Street Canyon reminded me of campus dormitories at the University of Buffalo, maximizing space for as many students as possible on limited real estate.

But later, I saw a more suspect reminder.

Driving from Austria into Hungary, where decades were lost under socialist rule, you first see urban space in the Hills of Buda.

An old neighborhood overlooks the Danube. But broken up in places because the Soviets replaced single family homes with monotonous worker housing, quashing personality and artful design.

Visitor compare the architecture to “early Stalinist.”

And filmmakers come to Main Street for its East Berlin look.

That’s unfair because once inside, you find living quarters that contrast the external dullness of the building. Arresting views, exceptional amenities and a community living nothing like under the harness of socialism.

But standing on Main Street or walking by the WIRE buildings, you wonder why planners hid the waterfront. A single artery obscures the East River as if we’re not on an island.

Why would anyone build a Main Street, in a planned community yet, that skirts the rear end of an historic church and an even older farm house?

Main Street Shadows

Eight years after Hudson and The Related Companies struck a deal with the Roosevelt Island Operating Corp. intended to spur development on Main Street, we still see numerous vacant storefronts.

A bakery, a hardware store and a chiropractor did business not long ago. There was a thrift shop. And lots of unpaid rent.

Unlike RIOC, which did so for years, Hudson and The Related Companies, commercial operations, can’t subsidize businesses that aren’t viable.

Virtually every business that closed on Main Street left a pile of debt as a parting gift to Roosevelt Island.

Each struggled to the end, but few, if any, will ever repay RIOC. In the end, the business models didn’t work, no matter how much forgiveness RIOC invested.

Demographics are a big issue on Main Street because our businesses have little draw for off-Island customers. Low population coupled with discretionary spending limits prevents variety in businesses.

How many bakeries thrive the wealthier, more densely populated Upper East Side? How many hardware stores?

If a successful formula is one of each for every 10,000 residents, which is what surviving on Roosevelt Island requires, bakeries and hardware stores would open on every block.

They don’t, and economics are the reason. Internet shopping’s made it even worse.

Roosevelt Island’s Main Street problem is reality itself

Expecting small retail businesses to survive unsubsidized on Roosevelt Island was never realistic.

But even if demographics aren’t favorable, infrastructure built backwards makes all obstacles harder to overcome.

You can’t take advantage of those sweeping river views Ed Logue wanted. You can’t enjoy the simple welcoming fronts of centuries old buildings.

Southtown also teaches us that an island needs to make a big deal of being an island. It’s why that community thrived from Day One.

Reimagining the Main Street Canyon

There are the challenges. Main Street is weirdly inside out, and we should think about solutions.

But the most important thing is that, as a community, we have resources that can jostle the status quo.

Struggling businesses and limited community engagement aren’t inevitable.

But who’s going to lead?

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