Ashland, OR, USA

The perfect 3 days itinerary

Nestled in the picturesque Rogue Valley, Ashland, Oregon, is renowned for its vibrant arts scene, particularly the Oregon Shakespeare Festival, and its stunning natural beauty. This charming town offers a delightful blend of cultural attractions, outdoor adventures, and culinary delights. With its quaint downtown, beautiful parks, and proximity to the Cascade-Siskiyou National Monument, Ashland is a perfect destination for those seeking both relaxation and exploration. This itinerary will guide you through the highlights of Ashland, ensuring you experience the best of what this unique town has to offer.

What to do in Ashland?

This 3 days itinerary is the perfect guide to the best things to see in Ashland. It includes day-by-day activities, travel tips, and the top places to visit.

Day 1: Cultural Immersion and Scenic Strolls

Morning

Begin your journey in Ashland with a visit to the Oregon Shakespeare Festival, one of the oldest and most prestigious regional theater companies in the United States. Depending on the season, catch a matinee performance or take a backstage tour to learn about the festival's rich history and production techniques.

Afternoon

After immersing yourself in the world of theater, take a leisurely walk through Lithia Park, a 93-acre oasis in the heart of Ashland. Enjoy the beautifully landscaped gardens, duck ponds, and walking trails. Be sure to visit the Japanese Garden for a moment of tranquility.

Evening

Conclude your day with a stroll down Main Street, exploring the eclectic mix of shops and galleries. Dine at one of Ashland's many acclaimed restaurants, such as Larks Home Kitchen Cuisine, which offers farm-to-table dishes that highlight the flavors of the Rogue Valley.


Day 2: Outdoor Adventures and Local Flavors

Morning

Start your day with a hike in the Cascade-Siskiyou National Monument, a short drive from Ashland. This area is known for its biodiversity and stunning vistas. Choose a trail that suits your fitness level and enjoy the fresh mountain air and panoramic views.

Afternoon

Return to Ashland and visit the ScienceWorks Hands-On Museum, perfect for families and curious minds. Engage with interactive exhibits that make science fun and accessible for all ages.

Evening

In the evening, explore the local culinary scene by visiting the Ashland Food Co-op, where you can find organic produce and local specialties. Pick up some ingredients for a picnic or enjoy a meal at one of the nearby eateries that source from local farms.


Day 3: Relaxation and Wine Tasting

Morning

Spend a relaxing morning at the Jackson Wellsprings, a community spa offering hot mineral springs, a pool, and wellness services. Unwind and rejuvenate in this peaceful setting.

Afternoon

Head out for a wine tasting tour in the nearby Applegate Valley Wine Trail. Visit some of the region's renowned wineries, such as Troon Vineyard or Cowhorn Vineyard & Garden, and savor the flavors of Southern Oregon wines.

Evening

Return to Ashland for a final evening of entertainment. Check the schedule at the Oregon Cabaret Theatre for a lively performance or enjoy a quiet evening at one of the local cafes, reflecting on your Ashland adventure.


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