The answer to this riddle is the Southern Hemisphere (or more specifically, South America).
Here is how it breaks down:
Cowboys in the middle: The famous gauchos (South American cowboys) roam the central grasslands and plains, like the Argentine Pampas.
Fisherfolk on the ends: The long, expansive coastlines on both the Atlantic and Pacific sides (like Peru and Chile) are world-famous for their massive fishing industries and coastal fishing communities.
Hipsters in the cities: Bustling, modern cultural hubs like Buenos Aires, Santiago, and São Paulo are filled with trendy neighborhoods, specialty coffee shops, and urban art.
Penguins all across the land: Multiple species of penguins (like the Magellanic, Humboldt, and Galápagos penguins) live all along the southern coasts and islands of the continent, not just in Antarctica!