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I know that NYC may top the recommendations , but the city stopped providing street food license , pr have to wait for years
I want to move to a city where ( Hotdog / Gyro) Pushcart business is very common and is working fine ?
Ive heard Portland, Oregon has many street food vendors, but I've never been there personally. I'd look into any college town with a decent downtown or entertainment district.
I wouldn't try selling street food in an area where the weather was rainy and / or cold. It would work best in an area where customers want to sit outside to eat. It would also be much more pleasant for the push cart operator to not be standing outside in the snow or rain.
We have push cart vendors in Detroit. Not a lot of them maybe five or six. Some of them stay out in the winter, some do not. It is rainy a lot here, but they still seem to get customers. Maybe you could sell umbrellas and gloves or stocking caps too. "Hot dog and a hat $10."
When it is really cold, I am sure they ware not out - no one is. But supercold is usually only a few days each year.
Here in Cedar City in southern Utah, a young couple looking to make ends meet started an open air pizza cart with a portable brick oven. It's a college town, but it snows here. The business took off and was at one point the top rated restaurant in the town- they were making dough from scratch and using quality ingredients. The brick oven would get hot enough that the orders cooked up in minutes. They were out there in all sorts of weather for years. They finally transitioned to a brick and mortar store front. The Pizza Cart is still very popular here. I think if you have the right product for the right customer base, it's a doable business model in a lot of places.
The Pizza Cart was located in a store parking lot before it became a brick and mortar restaurant. On really cold days, people would go into the store and shop while waiting for pizzas, so the store was happy to have the cart there. The good relationship with the local store allowed the cart to have a steady location, which I think helped.
Philadelphia PA is quite a walkable city. The beach towns in SoCal have lots of foot traffic. The Halal Guys have a brick and Mortar restaurant in Korea Town LA.
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