The Most Delightful Small Towns to Discover in Every State

14. Jacksonville, Oregon

Jacksonville, Oregon, nestled in the heart of the Applegate Valley Wine Trail, is a historic gem founded after gold was discovered in 1851. It even had the first Chinatown in the state. Over 100 buildings in the town are part of a National Historic District, preserving many original structures from the mid-1800s. Whether you're into scenic hikes or vineyard tours, Jacksonville offers a variety of activities.

The town is also known for the Britt Music & Arts Festival, an open-air event held in an amphitheater named after Peter Britt. This festival draws national talent from pop, country, alternative, and contemporary music scenes. Jacksonville hosts several other events throughout the year, including Chinese New Year, Oktoberfest, and the Oregon Wine Experience. Visitors can enjoy hiking trails, rent boats for a day on the water, and more.