1,000 km in a Day: Boston → Old Saybrook → NY → Poconos → Back

Boston to Poconos and Back — 1000+ km of Madness

Some ideas are good.
Some ideas are great.
And then there are ideas like this one — born at midnight, fueled by way too much confidence, and destined to become a full day of caffeine, mile-munching, horsepower, and questionable decision-making.

It started with my friend Ruifeng and me staring at a map and deciding that a thousand kilometers in one day sounded… reasonable. The plan: Boston → Old Saybrook, Connecticut → New York → Saravana Bhavan for a dosa → the Poconos → a wartime antique shop → dinner somewhere in Connecticut → Boston by nightfall. Easy, right?

Evening highway drive with a pink-and-blue sky
Cruising into the evening, chasing the last light of the day.

We hit the road with that giddy, first-hour energy that makes you believe you could drive to Alaska if you wanted to. The playlist was on point, the speed-limit signs were more of a gentle suggestion, and the miles started rolling by.

Somewhere between stretches of highway and coffee stops, we stumbled upon one of the most delightfully random pit stops of the trip — a vintage war-memorabilia shop. Imagine walking into a place where every shelf whispers stories from another time, from WWII helmets to submarine models.

Inside a vintage war memorabilia shop
Rows of history — from helmets to submarine models — all in one cozy shop.

Back on the road, the day kept surprising us. We passed a retro Gulf gas station straight out of the golden age of motoring — the kind of place where you half expect to see someone topping off a ’57 Chevy.

Retro Gulf gas station with classic cars
A gas station straight out of the golden age of motoring.

The Poconos greeted us with wide skies, rolling roads, and a few perfect stops just to take in the view. At the river’s edge, time slowed down for a moment — we could’ve stayed there all day if it wasn’t for the insane itinerary we’d signed ourselves up for.

Serene river view under a clear blue sky
Still waters and a moment to breathe before hitting the road again.

Scenic hilltop view with distant mountains
Nature’s own postcard — the Poconos showing off.

And then… the real mission. A food stop so legendary, so anticipated, that it was basically the midpoint trophy of this road trip — Saravana Bhavan. If you’ve never driven hundreds of miles for a dosa, you haven’t truly lived.

Saravana Bhavan storefront
Because no road trip is complete without a legendary dosa stop.

Inside, we didn’t just order food. We made a statement. A giant paper-roast dosa the size of a baseball bat landed on our table — crisp and golden — served with chutneys and piping-hot sambar.

Giant paper roast dosa served with chutneys and sambar
A crisp, golden paper-roast dosa — fuel for the next leg of the drive.

Oh, and medu vadas. Because why not double down on fried, fluffy goodness when you’ve still got hours of driving ahead?

Medu vada breakfast with chutney and sambar
South Indian comfort food to kick off the day’s adventures.

By the time we rolled back into Boston, the odometer had a new story to tell, our playlists had run out, and our stomachs were still full. A thousand kilometers in one day? Done. Would we do it again?
…Probably. Just maybe not tomorrow.