Lined with four-star hotels, winery tasting rooms, boutiques and world-class restaurants, Healdsburg Avenue has served as the town’s bustling main street since its inception in the 1800s.

Harmon Heald, a Gold Rush 49er, laid out the first town grid with a Spanish-style plaza. Originally part of the 48,000-acre Rancho Sotoyome land grant, Heald purchased a portion of the property in 1850 and built a store and post office at the center.

The city was incorporated in 1867. Businesses thrived around the plaza, the bustling West Street eventually became Healdsburg Avenue and today is one of the flourishing thoroughfares that attract visitors to the city from around the world.

Today, tourists, protesters and parade participants all amble down Healdsburg Avenue, one of the main drags in the city of 11,840.

Click through our gallery above to see how the street has evolved over the years.