Jacksonville, a little town with big charms, lures couples for romantic weekend excursions where they can recharge, reconnect and revisit small luxuries like excellent wine, exquisite meals and cozy hotels. Minutes from Interstate 5, this 1850s gold-rush town has a relaxing pace that feels decades and miles away.  

As Oregon's first entire district designated a National Historic Landmark, the quiet streets are flanked by beautifully restored, false-fronted and brick buildings that host shops, restaurants, tasting rooms and galleries. Surrounded by wooded hiking trails and within the Applegate Valley and Rogue Valley AVAs, it delights wine experts and novices alike. With a population of around 3,000, the town is a serious overachiever in terms of dining, wining and overnighting. 

Anchor Valley

World-Class Wines

The wine scene has deep roots: Swiss photographer Peter Britt planted the first vineyards in the 1850s. Thanks to diverse microclimates, soil conditions and vineyard plantings — from high elevation mountain sides to valley floor vineyards — both cool-climate grapes like Pinot Gris and warm-climate grapes like Malbec flourish in the region. In-town tasting rooms mean visitors can make merry on foot, no designated driver required. 

Sample a flight of red or white on the light-strung patio at Awen Winecraft, specializing in limited runs of boutique wines. Just a couple blocks away is the Anchor Valley tasting room in the 1872 Orth Building, where the bright, balanced pinot gris partners nicely with a cheese and charcuterie platter. 

Strolling and Shopping

Pick up some lovely jewelry or a scarf and hat at The Crown Jewel for four-season alfresco dining. Pico’s Worldwide specializes in fair trade and eco-friendly clothing, housewares and more. Browse the volumes at Rebel Heart Books, a classic small-town indie bookstore, and admire local talent at Art Presence, a collaborative community gallery on the grounds of the historic courthouse.

Top-Notch Dining

Even the most romantic retreat can’t survive on wine alone, and Jacksonville overflows with high-caliber eateries. The Jacksonville Inn, the granddaddy of the bunch, offers fine dining, a bistro and a lovely enclosed courtyard. Signature dishes include the savory blue cheese crème brûlée appetizer made with world-renowned Rogue Creamery cheese, as well as the New York steak with red wine demi-glace or the chicken stuffed with Oregon hazelnuts. The inn’s bountiful wine cellar has over 2,000 different wines from around the world. 

Sample locally sourced fare at C St. Bistro, where you can savor the forest in a rich, melty, wild-mushroom panini with three cheeses for lunch, or wild-mushroom farro risotto at dinner, paired with a 2018 Grenache from Peter William Vineyard, sourced from grapes located just 10 miles away. 

With four-season outdoor dining, Bella Union promises “pizza, pasta and pizzazz,” along with Sunday brunch where mimosas flow and housemade cranberry sourdough is transformed into exquisite French toast. Watching carbs? Diners can substitute spiralized zucchini for pasta. 

Magnolia Inn

Luxurious Lodging

A romantic getaway requires luxury lodging, and Jacksonville delivers. 

In town, the Jacksonville Inn has eight individually decorated rooms, including the Peter Britt room with a two-person spa tub. For an even more intimate experience, choose one of their four cottages, all with a fireplace and wet bar. The pet-friendly Magnolia Inn, built in 1928, serves an expansive continental breakfast that guests may enjoy on the second-floor covered veranda overlooking the gardens. TouVelle House, in a 1916 Craftsman home, has a sauna and outdoor spa along with a seasonal pool. Some rooms have a bonus lounge area or small sitting balcony. 

Out of town, Hummingbird Estate is a 47-acre nationally registered historic property with 18 acres of vineyards, a tasting room, manicured grounds and spacious suites. Animal lovers can check into Rellik Winery, where alpacas roam the fruit orchards. The whole house, which accommodates 14 guests, can be rented, or opt for a one-bedroom or three-bedroom suite. The indoor/outdoor tasting room serves wine from their 15 acres of grapes.