Looking at tiny Jacksonville now with all its cozy, Victorian-era charm, it’s easy to forget this was once one of the biggest towns in the Oregon Territory. Back in the day, it boasted — wait for it — 36 taverns, a Wells Fargo express station and buildings constructed in the wake of Oregon’s own gold rush.

Time forgot this little 19th-century boom town after the railroad came through and made nearby Medford its big stop. But that loss is our gain.

This Rogue Valley city is a National Historic Landmark now, its lanes lined with 150-year-old buildings that still bustle. You can still dine at the 1856 Bella Union Saloon on the main drag, browse the rooms of the 1873 Beekman house-turned-museum and sleep at the McCully House Inn, the McCully family home back in 1860.

These days, crowds flock here to soak up the atmosphere, browse the boutiques and wineries and catch a show at the Britt Music & Arts Festival on the grounds of pioneer photographer Peter Britt’s 80-acre estate. Those grounds, which include gardens, woodsy terrain and winsome trails, are open to the public year-round, by the way, for hiking and exploring.

We’ve settled in for the weekend at the boutique Magnolia Hotel, built in 1928 and completely redone last year by new owners Jeff and Nikki Bale. It’s bright and airy, with a dozen luxe guest rooms and irresistible reading nooks.

The hotel is walking distance to pretty much everything you’d want to see, from modern espresso bars to the historic Beekman Bank. During the summer, the bank is open on weekends with a living-history docent on hand to share colorful tales about Oregon’s gold rush, the bank’s Victorian-era safe and the impressive scale used to weigh gold dust and — we’re told — town babies.

At the moment, though, we’re perched at the bar at Jacksonville’s Miners’ Bazaar, an art project cafe and saloon run by Rogue Valley artist Rosie Taylor. Drawing paper and colored pencils are stashed at the bar, mosaic lamps dangle above, and there’s a menu of DIY craft projects, as well as one with sips and bites — veggie galettes ($10) and fancy grilled cheese ($10).

A studio filled with art supplies and craft kits await in back, and cozy nooks everywhere hold tables and chairs where you can sit and chat or create. Or you can do what we did, just marvel at the genius of an art bar as you sip a glass of, say, Quady North rosé or Long Walk Vineyards’ Field Red.

An actual Miners’ Bazaar opened just up the road in 1852, after trailblazers James Clugage and James Poole did a little, extremely successful panning and set off an Oregon gold rush. The bazaar was a trading post — a tent, really — that equipped the sudden surge of miners with everything from dungarees and pickaxes to tobacco and whiskey. As the mining encampment grew, so did its saloons, taverns and breweries — prolifically. Even the town bakery had a bar.

These days, Jacksonville’s tasting rooms are known for wine, not hooch, and the historic buildings house temptations such as the Violets & Cream Ice Cream Apothecary, the GoodBean coffeehouse and the Happy Alpaca Toy & Supply.

A giant toy alpaca stands near the front of Amy Kranenburg and Aaron Butler’s adorable toy shop, which opened in 2022 and stocks Legos, Brio trains, colorful Haba toys and other delights. It’s all so cute, it’s hard to imagine this wholesome little toy store was once the Marble Corner Saloon.

To be fair, “it was once a saloon” can be said of many of the historic buildings here. The Table Rock Billiard Saloon signage is still visible at the GoodBean coffee house, and the ice cream apothecary once housed Jacksonville’s first brewery.

But to hear all the lore requires a ride on the Jacksonville Trolley, which offers a 45-minute, narrated blast to the past. The driver points out landmarks and traces the discovery of gold and the rise of this boomtown, and every now and then, adds a dash of unexpected local history. Turns out the original Bozo the Clown — Vance DeBar Colvig, who performed as Pinto Colvig — was born here in 1892. He was the original voice of Disney’s Goofy and Pluto, too. Who knew?

There’s a wine trolley, too, that runs from downtown — home to several tasting rooms — to seven wineries farther afield. If you prefer to ramble on your own, the Jacksonville wine trail includes several especially tempting options, from Quady North and Dancin’ to Parkhurst Wine Cellars.

Mark Enlow — a Bay Area ex-pat who spent three years at Brentwood’s Hannah Nicole Vineyards — and his wife, Susan, opened their new Parkhurst tasting room on a hilltop just outside Jacksonville last fall.

The industrial-chic building is surrounded by an artful — and fire-defensible — expanse of concrete and crushed rock. (The original tasting room in the nearby town of Talent was devastated by the Rogue Valley’s 2020 Almeda Fire.) Inside, dramatic modern chandeliers hang from the high ceilings, giant glass roll-up doors bring the outside in and royal blue and violet velvet couches add color.

The winery name is a nod to Charlotte “One-Eyed Charley Parkhurst,” the legendary whiskey-drinking, cigar-smoking stagecoach driver who ferried passengers and gold on California’s wild frontier. No one knew she was a woman until after her death. Contemplate the legend as you sip Rogue Valley wines and enjoy shareable bites from the small, seasonal menu — grilled flatbread ($19), perhaps, or a cheese and salumi platter ($18).

Just a few minutes away, you’ll find Dos Mariposas Vineyards and Lavender, which began welcoming families and wine lovers in 2022 to stroll the lavender fields, enjoy live music by the pond and sip rosé and pinot noir on the patio. They offer food, too, including charcuterie boards for grown-ups ($21) and for kids ($5) to enjoy with lavender lemonade.

Take the trolley, and it will take you — and your rosé — back to town when you’re done.