Exploring Grants Pass and the Applegate Trail

Valley of Earthiness, River of Rogue Dreams

Wine and Food Along the Applegate Trail in Grants Pass Oregon

Outdoor photo of Pennington Farms in Grants Pass Southern Oregon

Driving from Medford to Grants Pass—and passing through the historic town of Jacksonville— get ready for farm charms and pure pastoral beauty along the quiet roads of Applegate Valley, where the Rogue Valley Food Trail and forward-thinking wineries await.

A photo of a jam jar from Pennington Farms on the Rogue Valley Food Trail in Southern Oregon

Troon Vineyards in Southern Oregon

Enchanted Forest Trailhead in Grants Pass Southern Oregon

Pennington Farms is in the heart of Applegate’s bucolic setting, and a part of the Rogue Valley Food Trail—a series of farm stands, u-picks, bakeries, cheesemakers, craft beverages, and much more—all committed to sourcing products grown and raised in Southern Oregon. Famous for their tasty array of jams (we like marionberry) and savory pies (even on a warm day, the chicken pot pie is sumptuous at a picnic table shaded by trees), Pennington’s baked sweets are also a treat: the Caramel Cuts were a Weekend Sherpa favorite.

photo of strawberry rhubarb treat inside Pennington Farms in Grants Pass on the Rogue Valley Food Trail

You are right to have grape expectations while visiting Grants Pass; the region’s Applegate Valley has its own AVA, and down-to-earth wineries abound. Wine Enthusiast magazine named Troon Vineyard an American Winery of the year for good reason. It’s one of the most progressive in the country with its “walking the talk” commitment to reducing environmental footprint through biodynamic farming. It’s also one of just two wineries with a Regenerative Organic Certified designation.

A group of people sitting outside at Troon Vineyard sampling wines in Grants Pass Southern Oregon

Troon’s beautiful outdoor setting amid the Siskiyou Mountains—and populated with sheep, chicken, dogs, honeybees, and grapevines— is worth the visit alone. Of course, the wines are wonderful too, so reserve a date. Tip: Do the self-guided garden walk at Troon.

Two people enjoying a wine tasting in the gardens of Wooldridge Creek Winery and Creamery in Grants Pass Southern Oregon

Combine a winery and a creamery (read, artisan cheese) at Wooldridge Creek in Grants Pass. Relax with a tasting on their outdoor patio overlooking the Applegate River Valley, and visit the creamery, where all the cheese-making magic happens. Bonus: Their resident cat is pretty adorable too!

Enchanted Forest: Just up the road from Wooldridge, the Enchanted Forest Trail has you entering into a lush meadow of flowers and butterflies flitting as if trying to sprinkle fairy-dust.

Butterfly in the meadow of the Enchanted Forest in Grants Pass

There’s a rusted old pickup for a bit of wonder, and it's meant to be there, so don't fret. While the Enchanted Forest has a lot of elements for a fairy-trail, take note: winter’s epic rainfalls have led to fast growing weeds and poison oak proliferations on many hiking trails across the west coast … wear long pants and sleeves or turn around if the going gets thick! The meadow of butterflies early on are enough to satisfy.

People wandering about near the picnic area of Weekend Beer Co. in Grants Pass Southern Oregon

STAY & EAT: With the Rogue River running right through the city of Grants Pass, a stay at The Lodge at Riverside puts you right above this free-flowing water. It makes for a good lullaby. For eats and drinks, head to the food truck and beer garden delights of Weekend Beer Company.

A lot of people sitting at picnic tables at Weekend Beer Company in Grants Pass Southern Oregon

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