Skip Willamette Valley for This Oregon Town with Awesome Wine, Music, and Gold Rush Pedigree

Jacksonville, Oregon

This tiny Gold Rush town near Medford is basically a perfectly preserved slice of the 1850s, but with way better wine. The whole place is a National Historic Landmark, packed with Old West buildings, amazing wineries, and some seriously good restaurants.

Think gold mining history meets Willamette Valley vibes, minus the tourist crowds.

Oregon’s Wealthiest Boomtown

Back in 1851, gold showed up at Rich Gulch and completely changed Jacksonville (they called it Table Rock City back then).

By 1859, this tiny place had grown into the largest trading center in the entire Oregon Territory. From 1853 to 1927, Jacksonville served as Jackson County’s seat, with major influence over early Oregon’s money and politics.

During those booming years, Cornelius Beekman set up Oregon’s very first bank here. He nearly became Oregon’s governor too, missing out by just a handful of votes in 1878.

Saved Because It Was Forgotten

When railroad planners decided to skip Jacksonville in 1884, the town’s economy took a nosedive. Things got even worse when they moved the county seat to Medford in 1927.

Because nobody had money to tear down old buildings or replace them, over 100 original structures stayed exactly as they were. By 1966, it became a National Historic Landmark (first on the entire West Coast).

The Food Scene Punches Above Its Weight

For a town this small, Jacksonville’s restaurants are surprisingly legit. The Jacksonville Inn serves up local ingredients in a building from 1861, while Las Palmas offers some of the best Mexican food in Southern Oregon. Don’t sleep on the food trucks either – they’re adding some modern flavor to the historic vibe.

Britt Gardens Is Concert Heaven

The Britt Festival isn’t your average music venue. It’s basically an amphitheater carved into a hillside, surrounded by trees and gardens that used to belong to a prominent pioneer. During summer, you can spread out a blanket, crack open some local wine, and catch everyone from classical orchestras to indie rock bands under the stars.

The Wine Scene Is Seriously Underrated

The Applegate Valley wine country flies under the radar compared to other Oregon wine regions, and that’s exactly why it’s awesome. The tasting rooms are chill, the winemakers often pour your tastings themselves, and nobody’s trying to upsell you on a wine club membership. Try Quady North for interesting Spanish varieties or Red Lily for killer Tempranillo.

The Historic Downtown Actually Feels Real

Unlike those tacky Wild West tourist traps, Jacksonville’s downtown is the real deal. Every brick building here has a story, from the old bank vault that survived multiple fires to the general store that’s been running since 1873. The best part? People actually live and work here – it’s a living, breathing town that just happens to look amazing.

The Cemetery Is Actually Cool

Yeah, we’re recommending a cemetery. The Jacksonville Cemetery sits on a hill overlooking town, and it’s basically an outdoor museum.

More than 5,000 pioneers rest here, including town founders, Chinese workers, and early settlers, all on a hillside across the valley. The oldest marked grave dates to 1859, though earlier unmarked burials probably exist.

Take walking tours through Historic Jacksonville, Inc. to learn about the founding families.

History Without Walls

Jacksonville created an innovative approach to sharing its past with a “Museum Without Walls” concept. The 1881 Old City Hall serves as an accessible hub for exploring the entire National Historic Landmark District.

This combines walking tours, trolley rides, exhibits, and digital tours you can download based on what interests you or how much time you have.

The museum gives you an interactive overview of Jacksonville history through programs like “Daily Life Then and Now: 1900 vs. 2025” and “Thirsty Thursday” talks about early saloons, beer, wine, whiskey, and local entrepreneurs.