Some cities tend to let their histories fade into the background, commemorating past events with plaques and monuments — inviting travelers to come snap a pic and move on to the next thing. Not Jacksonville, the ultimate Gold Rush town set in the rolling hills of Southern Oregon.
In this town of 3,000 people, built in the land grab of one of the state’s most important periods of growth, history is the ultimate present. It’s one of those rare places where you can step in and out of the past and come out with fresh eyes. That’s thanks to several generations of town elders who have preserved the city’s wide range of architectural styles and fostered a vivacious arts program, which rivals much larger cities.
This gift is best celebrated with a weekend pegged to the annual Britt Festival, one of the Pacific Northwest’s most compelling open-air music venues, which hosts a stellar series of concerts all summer long.

Trolley Tours and Walking Tours
The best way to get a quick scope of the town is via one of two trolley tours: a narrated history tour and a Jacksonville wine tour. The wine tour (Friday to Sunday, May-October) is your ticket to exploring some of the top tasting rooms in town in a safe, elegant and convenient way. Tickets include a free tasting at each winery. The history tour (May-December; days vary by season) is a narrated ride that highlights the town’s rich history, gracious vintage homes and landmarks that have stood the test of time. See the trolley tour website for ticket info and details.
If the majority of the town seems as if it were just repainted yesterday, you’re right. The impulse to preserve runs high here; a movement begun by an ambitious group of town leaders in the 1960s sought to document and save the numerous examples of Greek Revival, Gothic Revival, Italian Villa and Gold Rush-era architecture.
Every building here has a story, and you can step right into it through a number of walking tours, including the haunted history walking tour, cemetery walking tour and more.

Boutique Shopping and Art Galleries
If the ideal treasures for small-town shopping include family-run businesses, selectively curated showrooms, locally crafted goods, surprising vintage finds and an abundance of adorable signage, then Jacksonville’s main commercial thoroughfare, California Street, delivers major spoils.
Snag a handmade felted hat at The Crown Jewel, the latest young-adult release at the daring specialty bookshop Rebel Heart Books, global fair-trade finds at Pico’s Worldwide or luxe home goods at designer-owned Terra Firma Gift. The curator’s spirit is alive and well in the town’s galleries including the Art Presence Art Center, which displays the sometimes trippy, always wildly unpredictable work of 34 local artists in its member-owned space.

Cafes, Brewpubs and More Great Eats
Fab food picks are an easy find in Jacksonville. Locals pack the GoodBean Coffee every morning of the week. Umi Sushi draws a crowd with its pared-down space and fresh fish. The Jacksonville Inn has the most eclectic pairings of local lore and high-end food with a vibe set by the weekly regulars. The Mustard Seed Cafe is worth a side trip for a midday refuel and to gawk at a floor made of more than 120,000 pennies.
By far the most family-friendly adventure can be found tucked into a neighborhood just east of downtown, the Schoolhaus Brewhaus, the most authentic southern German restaurant I’ve found in the Pacific Northwest (a serious quest of mine after a year spent living in Munich). It’s a haven for imported pilsner, doppelbock, hefeweizen, dunkel and other beer styles set alongside a menu of hearty staples — all inspired by a destination restaurant in the German Alps near the tiny town of Garmisch-Partenkirchen. Long waits during Britt Festival season are no concern — the entire family can take in a round of mini golf, explore a historic train engine on-site, poke around an organic garden and rows of hops, or play at a pioneer-themed playground.

Destination-Worthy Live Music
We didn’t need to pull up any maps to get to the Britt Festival — we just followed the throngs of people carrying blankets, chairs and picnic baskets up the hill.
The festival is perched on an acoustics-perfect hillside just a few blocks southwest of downtown at the former historical estate of founding pioneer Peter Britt. It began as an exclusively classical venue but has evolved over half a century into a showcase of excellent music without any genre restrictions: Think Brahms and Beethoven one night and Primus or the Violent Femmes the next. Performances run mid-June through the last weekend in September and tend to sell out quickly.
I have no proof, but my kids might be the only ones in their elementary school who now know the history of Stephen Stills, Judy Collins and the rock ballad “Suite: Judy Blue Eyes.” We parked ourselves halfway up the hill and set in for an evening of storytelling, decades-old hits, sweet banter and raspy guitar riffs from American folk legends trading stories as the sun set and the stars came out.

Applegate Valley Wine Tasting
There’s no better way to cap a weekend than with a tasting tour of Southern Oregon’s award-winning warm-climate varietals, especially syrah, tempranillo, malbec and cabernet (with a designated driver, of course). Right in town, I like South Stage Cellars, which pours wines from throughout the Applegate Valley in an elegant, historic brick space on Third Street. Those in explorer mode should check out the wine shop at the Jacksonville Inn, which has more than 2,000 different wines, or hit the Applegate Wine Trail, a 50-mile, stop-as-you-will country ride between Jacksonville in the south and Grants Pass in the north, an area of the state where there is no hurry, no stress, just wine to sip and views to drink in.