Road Trip to Ashland, OR
This summer, hit the open road and make your way to charming Ashland. Surrounded by the beauty of the Cascade-Siskiyou Mountains and Southern Oregon wine country, Ashland invites you to immerse yourself in a world of timeless elegance, rich history, vibrant arts, and serene natural landscapes.
EXCLUSIVE OFFER
10% off Midweek Stay (Sun-Thurs) from May 15 – August 31
Top Things To Do in Ashland:
Theatre Under the Stars
Enjoy world-class performances at the Tony Award-winning Oregon Shakespeare Festival, where stories come alive in charming outdoor and indoor venues.
Wine Tasting with a View
Sip your way through the Rogue Valley Wine Country, where scenic vineyards offer rich reds, crisp whites, and unforgettable views.
Boutique Shopping
Peruse Ashland’s historic downtown, filled with local art galleries, curated shops, bookstores, and artisan markets.
Stroll Through Lithia Park
Wander tree-lined paths, and relax by the duck pond in this 93-acre park designed by the same landscape architect behind Golden Gate Park. Be sure to stop by the tranquil Japanese Garden.
Cascade Siskiyou Scenic Bikeway
Explore the beauty of Ashland and beyond on this 55-mile loop. Cycle past rolling hills, and biodiverse forests—all starting right from downtown Ashland.
Crater Lake & Hidden Waterfalls
Lace up your boots for a scenic day trip to Crater Lake National Park. Along the way, stop at breathtaking waterfalls before reaching Oregon’s 7th Wonder.
Stay at Ashland Springs Hotel
After a day of culture, wine, and exploration, return to the timeless elegance of Ashland Springs Hotel, your home base in the heart of downtown.
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Elegant guest rooms with European-style charm and modern comforts
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Relaxation awaits with our dry sauna and holistic treatments at Waterstone Spa
- Taste the Oregon story at LARKS Restaurant. Our charming sidewalk seating offers the perfect summer dining experience
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Steps from the theatres, boutique shops, and fine dining
Continue the Adventure! Best Places to Road Trip
Inspired by wanderlust, fresh air, and good vibes, here are some of the coolest spots in the PNW. From beach bonfires to historic hikes and spa days to seafood feasts—every leg of the journey is a new adventure. We even threw in our suggestions for where to stay at our partner hotels with exclusive discounts as well!