The White Mountains. It's like traveling back in time.

Get dinner at the continental in Saugus. Place hasn’t changed since it opened. Same waitresses and everything.

Cuba

^ this is the correct answer

Stockbridge. You’ll be in a Norman Rockwell painting, literally. Not much to do there though.

At this point they should land mark it and try the scampi while they’re putting up the plaque

The south, ideologically

Which painting will I literally be in?

In Massachusetts, go to the Wayside Inn and order the turkey dinner. Don't worry, it is always on the menu. In New Hampshire, go the the Common Man.

Gorham, NH is a good home base in the White Mountains if you want to be stuck in the 1950’s.

They tend to keep the big chains out. A lot of places in Maine are the same way.

I'm gonna assume you're white lol

Depends on which one you want to be in, he has many of Main Street Stockbridge and surrounding areas.

Or maine

Kingston, NY! Their infrastructural social policies have remained largely untouched since the 50s so you'll see lots of classic racism, hospital-acquired infections, punishment as mental health treatment, sinkholes in roads and failed anti-drug policies. At night, you can see the flickering methane torches burning near the top layer of the landfill!

West Roxbury

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Yes . I would go to Phu-Ket Thai Restaurant or Viva Mi Arepa. Both are great.

Diners in and around Lowell National Historical Park. Arthur's Paradise Diner on Bridge Street even serves traditional mill worker sandwiches.
There's a large variety of more typical 50's style diners for example Four Sisters Owl Diner. One could make a study. They're interesting to see from the outside once you've had enough to eat.

Of course the mills were still operating in the 50's so the park has some worthwhile exhibits. Come on a nice day and walk around, lots of 50's architecture like https://www.google.com/maps/@42.644723,-71.3136828,3a,36.2y,341.93h,95.74t/data=!3m7!1e1!3m5!1s2_C5B3_S00wMvQ4izfrKDg!2e0!6shttps:%2F%2Fstreetviewpixels-pa.googleapis.com%2Fv1%2Fthumbnail%3Fpanoid%3D2_C5B3_S00wMvQ4izfrKDg%26cb_client%3Dmaps_sv.tactile.gps%26w%3D203%26h%3D100%26yaw%3D214.984%26pitch%3D0%26thumbfov%3D100!7i16384!8i8192

You paint a beautiful portrait with words!

In Doc Brown’s Delorean.

Parts of Vermont and the parts of Maine that tourists don’t go to are as close as you will get within driving distance. Start by finding places with no cel service and no Walmarts/dunks/McDonald’s nearby.

Or go to Cuba.

The Grist Mill nearby is also pretty neat

Deep south

That was my first thought, but really just the American cars are 1950s. They did get some Soviet cars and those friendly with the government have some Mercedes. But the rest of the country is just run down old buildings or Soviet era buildings, some newer ones going in too. It's not at all 1950s living.

Pleasant Cafe in Roslindale

Wildwood NJ

George's Coney Island in Worcester.

Like walking into a time machine.

I got stuck in a storm up through there and got a room at a roadside motel with a restaurant /bar attached to it. Like a different world. Arguably one of the best times of my life.

Pine Cone Inn, somewhere new Hampshire.

This diner in Hudson: https://www.victors50sdiner.com/

Stoneham

Lmaoo I was gonna say it 😂

Lol this is the whitest shit.