Drive, hike and soar through this scenic corner of Southern Oregon.
In the peaceful countryside between Grants Pass and Medford in Southern Oregon’s Rogue Valley region, the Applegate Valley is easy to get to from Interstate 5 but feels worlds apart from any hustle or bustle. You’ll find quiet two-lane roads and the rushing Applegate River linking world-class wineries, epic hikes, cozy lodges and one of the country’s best paragliding sites — all close enough to take in on a long weekend. Here’s how to make the most of a 36-hour getaway to the Applegate.
Day 1: History and Wine Tasting in Jacksonville
One hundred and seventy years ago, gold miners descended upon tiny Table Rock City in the hills west of Medford with dreams of striking it rich. Today that mining town is called Jacksonville, and while you’re unlikely to find much in the way of precious metals, it’s still a magnet for architectural and culinary treasure seekers.
Jacksonville was named a National Historic Landmark for its beautifully preserved 19th-century downtown, and experiencing the compact, walkable core on foot is one of the town’s great pleasures. Start the afternoon with a stroll through ornate Victorian homes and brick-faced commercial buildings, many of which now house chic boutiques and appealing ice cream shops. From June to October, you can hop on a narrated Trolley Tour that leaves several times per day from the Visitor Information Center, or take advantage of guided offerings from Historic Jacksonville, such as a tour of the C.C. Beekman House Museum, which still holds many of the original interior furnishings from the 19th century.
Afterward, head just east of town to DANCIN Vineyards to experience the Applegate’s uniquely diverse wine culture. Long, warm growing seasons mean this region can grow dozens of different grape varieties, from light-bodied pinot noir and crisp chardonnay to richer styles like zinfandel and sangiovese. Choose a glass or flight featuring estate wines to pair with a sausage and broccoli rabe pizza or stuffed mushrooms as you watch the sun set over rows of estate vines. Then return to Jacksonville to spend the night at the historic Jacksonville Inn — there’s even an on-site Wine Lounge for a nightcap.
Day 2: Public Art and Paragliding
In the morning, grab coffee and pastries at Cerberus Coffee, a hip coffee shop that roasts its own beans. Then head for Woodrat Mountain a few miles south of town, where Sundog Paragliding School helps the otherwise earthbound take flight. If you’re new to paragliding, you’ll want to book a tandem flight. While the instructor manages the sail, you’ll be free to enjoy the incredible scenery of the Applegate Valley from a true bird’s-eye view. You can even arrange to land at a local winery like LongSword Vineyard, where you can celebrate your flight with a glass of sparkling chardonnay.
If you’re looking for something a little less adrenaline pumping, head southwest from Jacksonville on Highway 238 for about 7 miles to the 88-acre Cantrall Buckley Park, which sprawls along the Applegate River. There are campsites, day-use areas and a network of trails here, but the real draw is the Cheryl D. Garcia exhibit, which consists of 11 larger-than-life metal sculptures of local flora and fauna, including mock orange, Oregon iris, and the Monarch butterfly. There’s also an interactive sundial: Stand on the tiles as instructed and your shadow will indicate the time.
If that sundial tells you it’s time for refreshments, continue on Highway 238 about 7 more miles to The Station Market and Cafe. Choose a savory house-baked focaccia and a strawberry lemonade, or check to see if there’s a food cart outside. You can also stock up here on local wine, snacks, pasture-raised meats and other products from the many farmers that call the Applegate home.
Right across the street is The Lindsay Lodge, an ideal place to spend the night in the heart of the Applegate. Constructed from peeled pine, fir and redwood logs, the vibe here is rustic yet refined, with views of the Applegate River from every room on the 3-acre property. Spend the afternoon relaxing by the river, then head in to the on-site restaurant for pan-seared salmon or a flat-iron steak.
Day 3: Pastries and a Hike
Wake up with a hankering for something sweet? Head northwest on Highway 238 for about 7 miles to Pennington Farms, a berry farm that dishes up delectable house-made pastries, pies and jams. Enjoy a Danish and a cup of coffee on the sunny patio — and don’t miss perusing their preserves section, which captures the flavors of peak-season produce for year-round enjoyment. If it’s Sunday and Pennington Farms is closed, keep in mind the lodge serves a delightful Sunday brunch. Find even more options for family farms, farm-to-table restaurants and more along the Rogue Valley Food Trail.
After breakfast cruise north about 9 miles to Cathedral Hills, just south of Grants Pass, where a 10-mile trail network winds through Douglas fir and ponderosa pine forests. Hikers, cyclists and even horseback riders will find plenty of options for short or long routes here. From here it’s a quick drive into downtown Grants Pass for lunch and on to your next adventure.
