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Your Oregon Holiday Destination: Jacksonville and the Applegate Valley

Jacksonville and the Applegate Valley

’Tis the most wonderful place when snow comes to Southern Oregon

written by James Sinks

IMAGINE A storybook gold rush-era town, where stately houses and brick boutiques glisten with holiday charm, where recreation options beckon and where cocoa and award-winning wines take turns warming you up.

Also, imagine it’s not only Santa checking to see if you’re naughty or nice. Bigfoot might be watching, too.

In Southern Oregon’s Jacksonville and the neighboring Applegate Valley, imagination meets reality.

Here, as the mercury falls, lights go up and the nostalgia comes out.

Each year, a Victorian Christmas celebration offers a tantalizing escape to a simpler time. Distant are big city stressors, and real world depressors. Soak in the decor, food, farm stands, spas, musicians, trails, parade and the romantic downtown that practically begs you to hold hands inside your winter gloves.

This year, the tradition gets bigger. Jacksonville Trolley buses that previously dispatched to nearby Medford for Christmastime tours will be staying in town instead, now to proudly zigzag a local-only panorama.

“We will be showing off our history in addition to our lights,” said Brian Dunn, the local chamber president, a building contractor and architect of the new holiday experience. An added incentive?

There’ll be hot chocolate for the forty-five-minute tours.

When wagons were still creaking west on the Oregon Trail, the glitter of gold lured the early arrivals to the rough new town, first known as Table Rock City and notoriously the site of the Oregon Territory’s first recorded hanging.

Thousands of nearby mines yielded millions of dollars of the precious stuff, and helped to finance Victorian-style mansions and the state’s first Chinatown. One settler, a Swiss immigrant named Peter Britt, also planted orchards and established the Pacific Northwest’s first winery.

His winery didn’t survive Prohibition and the Great Depression, but today there’s no shortage of them—eighteen in total—on the Applegate Valley Wine Trail.

Also a photographer, Britt is credited with the earliest known photos of Crater Lake. If he were still around, he’d undoubtedly also point his lens—like the rest of us—at the magical transformation of his hometown. In those days, it might have been hard to imagine.

Come December, it’s now hard to imagine it being more perfect.

The holiday parade during Victorian Christmas celebrations in historic downtown Jacksonville.
Tony Kay Photography/Jacksonville Chamber of Commerce

Day 1: Carrot Cake, Shopping, Holiday Lights Tour

Backroad byways are one of Oregon’s traveling joys, inviting you to revel in stunning vistas, wave to curious animals and prowl random points of interest. The journey on state Highway 238, which meanders 30 miles from Grants Pass through the Applegate Valley to Jacksonville, covers all those bases. A bonus? Good snacks.

At the 145-year-old Provolt Country Store & Deli, a destination itself, the star attraction is the house-made carrot cake, under a pillow of cream cheese icing and with almost half its weight in carrots. In gold country, the more carrots, the better.

Following the mining rush, Jacksonville became largely an afterthought, and the county seat even moved next door to Medford. Without much redevelopment pressure—it’s still home to less than 3,000 people—the town became a time capsule of sorts and in 1966 was declared a historic district in its entirety. Now, tourism drives the economy.

Holiday list in hand, browse the four-block, once-boomtown downtown to a smorgasbord of bedecked clothing boutiques, antique peddlers, kitchenware and jewelry shops, and bougie watering holes. If you like interpretive signs, find a bonanza of those, too, including at the site where remnants of Chinatown were unearthed.

There’s no longer snooker, but you can scout seats and snacks at GoodBean Coffee, in a circa-1852 billiards hall and saloon. Breakfast is served until 2.

GoodBean Coffee is served inside an 1852-era billiards hall.
Travel Southern Oregon

Impervious to temperature and have your pup in tow? Violets & Cream candy shop sells twenty-eight ice cream flavors for people, and three options for furry friends. Stiff from the drive? Several local spas including Belita Space offer rubdowns.

On South Third Street, local artisans are the stars in an inviting country cottage at Artist & Gardener, started eight years ago by a pair of California escapees. The artist founder, Todd Lovett, paints watercolors on site, while Mark Sutter, the gardener, dresses up the yard and porch.

After a tasting room or two, burrow into your holiday coat and queue for the Holiday Trolley Lights Tour. The route will whisk past the courthouse-turned-city hall, several Victorian houses-turned-hotels including elegant Kubli Haus, and the Bigham Knoll Drive campus, home to the original schoolhouse, the local Rogue Brewery and mini golf, weather-permitting. A live-action Nativity scene is also planned.

Nightly tours begin after Thanksgiving. Save spots starting Nov. 1.

Afterward, inspired fare and mellow vibes await at Gogi’s Restaurant, where the wine list is long, the wooden bar is artful and seasonal dishes feature the bounty of Southern Oregon. Try the smoked salmon cakes and semolina gnocchi with artichoke purée.

For toe-tapping post-dinner entertainment, high step into Italian eatery Bella Union or the South Stage Cellars tasting room. Or, if you prefer pool, a jukebox and taxidermy, head to local hangout J’Ville Tavern—the oldest bar in the Rogue Valley—where the drinks are strong and the conversation is lively. The stuffed animals? Not so much.

Day 2: Applegate River, Bigfoot Trap, Wineries

The oldest Oregon residence that’s now an inn, the circa-1860 McCully House was saved from bankruptcy when Jane McCully—abandoned by her husband—made pies and bread for local miners.

Fittingly, today there’s a cozy bakery on site, with pastries, steaming espresso and a filthy-rich chocolate-frosted gluten-free cake. Take that, creditors.

The Victorian McCully House Inn in Jacksonville.
Apex Video Tours/McCully House Inn

Born in the Siskiyou Mountains, the Applegate River—named after Lindsay Applegate, who helped scout the Applegate Trail through Southern Oregon—weaves past old mines and present-day gold panning beaches, clusters of wineries, hemp and berry farms, a hang glider jumping-off spot and, some believe, one big hairy fella.

Spurred by those myths, the Applegate includes an Oregon see-it-to-believe-it destination, the world’s only Bigfoot Trap.

To get there, the 1.8-mile in-and-back hike on the Collings Mountain Trail fords a seasonal creek and tightropes through enough poison oak that leaving the path would be a rash decision. Up a hill at about the three-quarter-mile mark, you can peer inside the burly wooden hut with a heavy steel door. Built in 1974 and now decommissioned, it caught a few hungry bears, but no Bigfeet.

A long-standing Bigfoot trap was decommissioned but stands as a monument to folklore.
James Sinks

Even if you don’t meet Sasquatch, you can still toast the trek with a beverage oddity: At roadside Code 3 Coffee & Snacks, the pickle juice lemonade will surprise your taste buds. Even better, sip whilst you stroll through covered McKee Bridge, which has its own historical society and, some years, yuletide decor.

Applegate wineries offer a range of tasting experiences, from mom-and-pop operations to multimillion dollar chateaus. Yet one name keeps coming up when you ask for tips, and that’s Red Lily Vineyards, where Spanish wine flights and perky Lily Girl Rosé arrive in test tubes in a farmhouse with a river rock fireplace.

The beautiful barn winery of Red Lily Vineyards.
Chris Martin/Red Lily Vineyards

A decade ago, Wooldridge Creek Winery became the state’s first combined winery and creamery, sourced with organic milk from neighboring Noble Dairy. It’s a great place for lactose-loving lunch and gift shopping from the cooler, if you have friends who like cheese.

Nearby, Rosella’s Vineyard & Winery is unassuming and sublime, with the wine often poured in the tiny tasting room by owner Rex Garoutte. They also sell homemade zesty pretzels called Spretzels for $5.

For a contrast next door, explore the sprawling grounds and cavernous great hall at Schmidt Family Vineyards, with a lake outside and twenty-two varietals and warmth inside. For holiday merriment, they burned a wooden Grinch in 2023, and plan a similar event again.

Don’t miss Pennington Farms store and bakery, with berries, pies, a kaleidoscope of jam (gift list fodder!) and dreamy cocoa inspired by Judy’s perfect hot chocolate from the Santa Clause movie, all with a happy, laid-back Aloha surfer vibe—courtesy of one of the owners, who grew up in Hawaii.

Relax and unwind at The Lindsay Lodge, named after the onetime explorer. Once known as Applegate River Lodge, the hotel boasts themed rooms and big bathtubs, a 12-foot Christmas tree in the lobby and a farm-to-table restaurant and bar—all overlooking the namesake river, as it slides past into the silent night.

Day 3: Winery Brunch, Santa, Pigeons

Vacation is typically a game of hide-and-seek with calories, and the calories always seem to win. But you can ditch a few on a bike on the lightly trafficked roadways of the Applegate.

It’s temporary. You’ll find those calories again with flavorful brunch and morning cocktails at the Italian estate-evoking DANCIN Vineyards, where the logo is a ballerina but the name is a blend of the medal-winning winery’s founders, Dan and Cindy Marca. While DANCIN’s menu rotates (cross your fingers for the tri-tip hash), seating is most always limited, so reserve ahead.

An aerial view of DANCIN Vineyards, where great wine and pizzas come together in its piazza.
DANCIN Vineyards

Weekends in December, Santa sets up shop downtown, if you want to sneak a peek at his list. Naughty? Nice? Hopefully, a bit of both.

In addition to its old buildings, Jacksonville also loves its open spaces, including the onetime property of Peter Britt, now home to a summer music festival. Behind the historic Beeker House, built by a onetime banker, stroll a 1-mile loop through a hillside native plant arboretum to valley views.

You’ll see critters and maybe a few birds, but that probably won’t prepare you for the cooing menagerie at Sindy’s Pigeon Service, a rescue business that’s run by a retired California attorney and her husband.

“Pigeons’ love is enormous,” Sindy Morgan said, cradling a black-and-white named Oreo and kissing him on the head.

For free, tour the aviary, where eighty feral and rescued domestic birds with names like Boris, Beverly and Brenda fly about. A hat is a very good idea. Sindy also gives school talks, and builds urban pigeon houses where eggs can easily be collected for population control, as a way to reduce pressure to euthanize the birds.

Sindy’s Pigeon Service is a great stop for bird lovers.
Sindy’s Pigeon Service

Make a final visit to California Street for some sanitizer and any remaining gift shopping, then step into French-inspired C St. Bistro for sourdough pizza and tomato soup with lemon pepper sour cream and kalamata olive purée. Started in 2010 by Paul Becking, a onetime Santa Barbara chef who’s committed to “bad-free” ingredients, the place may look tiny from the outside, but the flavors sure aren’t.

In a way, that’s also an apt metaphor for Jacksonville and the Applegate. Small yet surprising, flavorful, natural and artful. And especially during the throwback holidays, decidedly bad-free.

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