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Psh easy

Gramps walked down a street named uphill to school and then he walked down the same street home every day.

Answer:

Grandpa's house and the school were both situated at the top of separate hills, so he had to walk downhill and then uphill in both directions.

possibly

The school had multiple buildings and Grandpa's first class in the morning was in a building on a hill that was uphill from his home. And his last class in the afternoon was in a little valley at the base of the hill so it was uphill back home. During the day, he moved up and down to get from building to building for his classes.

Poor Grandpa. He forgot to mention the snow and 15 miles.

He lived on a small iceberg floating in the ocean. The residential area is on one side and the school is on the other. When everybody is at home, the residential area is more heavily weighted and the berg slopes upward towards the school. When everyone is at school, that side is heavier and the way home is uphill. Of course, when about half the people have crossed the midpoint, the iceberg would tilt the other way, but maybe your grandpa was an early riser and a diligent student and left before everyone else, and also went home early, so for him it was uphill both ways. For the lazy folks that slept in and arrived late (and maybe because of that got kept late for detention), it was downhill both ways.

Your Grandpa:

wasn't lying. He lived on a Penrose Field, with the school on the other side. Uphill both ways, unless of course some days he felt lazy and went downhill both ways!

He had a dog named "uphill". $ $ $ $

He lived part way up a mountain and went to skiing school. Uphill to the lesson at the top, and uphill from the bottom of the slope back home.

A possible answer

Your grandpa travelled to and from school on a team boat that used a human treadwheel system of propulsion.
To operate the paddles and gain forward motion, he would have to walk uphill in both directions.

This is trivially true if

there is at least one hill or valley in between the two endpoints of the journey, in which case the person walking will go both uphill and downhill both ways.

I believe that this question has been most accurately answered in the following scenario.
Your grandfather lives on one side of a ravine. The building is on the other side. A tightrope with room for some slack is strung between the two sides.
Because of the weight distribution, when your grandfather uses the tightrope, he would have to walk uphill either way to reach the end of the tightrope.

Grandpa's family owned six houses, all distributed at different heights along the same mountainside. (Needless to say, his family was quite wealthy.) There were also five different schoolhouses along the mountainside, each one in-between two of Grandpa's houses. On Monday, Grandpa would start at the lowest house on the mountain, and would walk uphill to the lowest school. When school was done, he would walk home, uphill, to the second-lowest house. The next day, he would walk uphill to the next school up the slope, and so on. Each morning he would walk to a different school, and then go home to a different house. On the weekend he would ski down the mountain and start over.

An answer that avoids Grandpa conveniently omitting that he

also walked downhill

He...

walked his bike uphill, and rode it downhill!

Possibility:

His house was on a hill above the school, but the school was at the top of a high-rise building, higher than his house. He walked up stairs in the morning but took the elevator down and then walked the rest of the way in the afternoon. Thus he had a walking elevation gain both ways.

Unironically this actually happened to me when I grew up.

There was a...

valley in between my house and the school so I would start off downhill then have to go up hill both ways

Your grandpa

lived on the top of a hill and his school was on the top of a different hill. Both the school and his house had a mechanism to get to the base of the hill quickly, such as a fireman's pole or a cart on rails going downhill. However, although the fastest way to go downhill, none of these mechanisms could be used uphill, so he had to walk uphill both ways, but never walk downhill!

Grandpa lived on a...

houseboat, which great-grandpa would dock overnight in the bay. Grandpa would walk uphill to school, and while he was there, great-grandpa would sail the boat upstream through some locks. By the time grandpa got out of school, he'd have to walk uphill to the houseboat, before sailing back downstream to the bay.

Alternatively, Grandpa lived on a...

houseboat and went to a maritime school that was only in session between low and high tide. He'd get off the boat at low tide and walk uphill to school, but when school let out at high tide, he'd have to walk uphill to get back to his house.

This is how I always pictured it as a child.

The school is built on the side of a mountain. The entrance is at the top. The exit is at the bottom. The house is in the middle. This can also explain why it was "in the snow" as many of these stories are. :)

Picture:

Grandpa lived in the valley of a mountain with the school halfway up. In the morning he'd walk uphill to school. After school he'd walk uphill to a cliff at the top of the mountain overlooking the valley. He'd then paraglide home.

Is "Uphill" his dog, which he walked to school with him everyday? Therefore he "walked Uphill both ways"?

Grandpa had to work at a job after school which was located at a lower elevation than his house, which in turn was lower than the school. So, in the morning he would walk up a hill to school, then after school he would walk downhill to where he worked (not mentioned), then at the end of work his trip home would be uphill again.

Grandpa had to walk into a headwind both ways - perhaps he lived somewhere with a regular and predictable weather pattern, and the prevailing wind would reverse twice a day.

Riding/walking/running into a headwind would replicate the added resistance of walking uphill, same as on a soft sandy beach.

Inspired by cycling, and this definitely makes the flats feel like hills.

There's quite a few "ravine|canyon|valley" in the middle answers, where each trip is downhill then uphill. My personal walk to elementary school had a ridge in the middle. Same kind of answer, but opposite. First uphill then downhill both ways.