21 Unmissable Experiences in Ashland, Oregon

Nestled in the lush Rogue Valley, Ashland, Oregon, is a hidden gem for travelers craving a blend of culture, nature, and culinary delights. Whether you’re an art aficionado, an outdoor enthusiast, or a foodie on a mission, this charming town delivers in spades.

Here’s your ultimate guide to 21 things you absolutely must do in Ashland.

Key:

💲 = Budget-friendly

💲💲 = Affordable

💲💲💲 = Moderate

💲💲💲💲 = Pricey

💲💲💲💲💲 = Luxury

1. Catch a Play at the Oregon Shakespeare Festival 💲💲💲💲

Ashland’s claim to fame is its world-renowned Oregon Shakespeare Festival. From March to October, the festival stages classic and contemporary works that rival performances on Broadway. Snag your tickets early through their official site to secure the best seats.

Local Tip: Sit in the balcony for a surprisingly intimate view without the hefty price tag.

2. Wander Lithia Park 💲

Designed by the same visionary behind San Francisco’s Golden Gate Park, Lithia Park offers 93 acres of stunning landscapes. Whether you’re up for a leisurely stroll or a peaceful afternoon picnic, this park is your go-to spot. Download a self-guided tour map from Ashland Parks & Recreation to explore its hidden gems.

Local Tip: Look for the duck pond; it’s a favorite among locals for a tranquil moment.

3. Indulge in a Wine Tasting Tour 💲💲💲💲

The Rogue Valley is an emerging star in Oregon’s wine scene, boasting exceptional Pinot Noirs and Viogniers. Book a tasting at Irvine & Roberts Vineyards to experience their panoramic views and expertly crafted wines.

Local Tip: Skip the weekends if you prefer a quieter, more personalized tasting experience.

4. Explore the Ashland Art Center 💲

Support local artists by visiting the Ashland Art Center, where you’ll find unique, handcrafted pieces. From ceramics to paintings, you’re bound to discover something special.

Local Tip: Check out their event calendar for art walks and workshops open to visitors.

5. Dine at Larks Home Kitchen Cuisine 💲💲💲💲💲

Treat your taste buds to the freshest seasonal ingredients at Larks, a favorite for farm-to-table dining. Their lavender crème brûlée is an absolute must-try.

Local Tip: Ask to sit on the patio for a lovely alfresco dining experience in the summer.

6. Stargaze at the ScienceWorks Hands-On Museum 💲💲

By day, the ScienceWorks Museum is perfect for interactive exhibits, but their stargazing nights are truly special. Peer through telescopes and learn about constellations under the clear Oregon sky.

7. Visit the Historic Railroad District 💲

This charming neighborhood is a blend of Ashland’s history and modern flair. Stroll through boutique shops and cafes tucked into beautifully preserved historic buildings.

Local Tip: Stop by Noble Coffee Roasting for a locally loved espresso.

8. Take a Day Trip to Crater Lake National Park 💲💲💲

Just a short drive from Ashland, Crater Lake is a natural wonder you can’t miss. It’s the deepest lake in the U.S., and its vibrant blue waters are a photographer’s dream. Visit the park’s site for trail maps and updates.

Local Tip: Arrive early to avoid the crowds and catch the sunrise over the lake.

9. Savor Chocolate at Branson’s Chocolates 💲💲

Branson’s Chocolates is a family-owned shop known for its artisanal treats. Try their lavender truffles for a uniquely Oregonian twist.

10. Tour the Ashland Springs Hotel 💲💲💲💲

Step into the past with a visit to the historic Ashland Springs Hotel. Its art-deco charm and elegant design make it a perfect backdrop for Instagram-worthy photos.

11. Sample Local Brews at Standing Stone Brewing Company 💲💲💲

Nothing says Oregon like craft beer. Pair your pint with a house-made pretzel at Standing Stone for the ultimate casual meal.

12. Take a Hike on Grizzly Peak 💲

For panoramic views of the valley, Grizzly Peak Trail is a must. This moderate hike is well-marked and offers stunning vistas.

Local Tip: Visit during late spring when the wildflowers are in full bloom.

13. Shop at Paddington Station 💲💲💲

This quirky boutique has everything from stylish home goods to unique fashion finds. It’s the perfect place to pick up a souvenir or gift.

14. Unwind at Waterstone Spa 💲💲💲💲

Relax and rejuvenate at Waterstone Spa, where you can enjoy a massage, facial, or even a mineral salt soak.

Local Tip: Book a morning session to enjoy their quietest hours.

15. Discover Local History at the Southern Oregon Historical Society 💲💲

Dive into the area’s rich history with exhibits that cover everything from Native American heritage to pioneer life.

16. Enjoy Live Music at Brickroom 💲💲💲

Brickroom is known for its vibrant atmosphere and live music events. It’s a great spot to wind down your evening with good tunes and great company.

17. Cycle Through the Bear Creek Greenway 💲💲

Rent a bike and ride along this scenic trail that stretches through the valley. It’s an excellent way to explore beyond the town.

18. Take a Cooking Class at Ashland Food Co-op 💲💲💲

Learn how to whip up Oregon-inspired dishes with locally sourced ingredients. Visit their event page to sign up for a class.

19. Stop by Noble Coffee Roasting 💲💲

Kickstart your day with a cup of sustainably sourced coffee at Noble Coffee. Their cold brew is a local favorite.

20. Visit North Mountain Park Nature Center 💲

Learn about Ashland’s diverse ecosystems through interactive exhibits and walking trails.

Local Tip: Keep an eye out for wildlife like deer and rare birds during your visit.

21. Explore the Rogue River by Raft 💲💲💲💲

Thrill-seekers will love rafting the Rogue River. Book a guided tour for an unforgettable adventure through rapids and calm waters alike.

Ashland, Oregon, is more than just a picturesque town; it’s a destination that captures the heart. From cultural experiences to natural wonders, this town offers something for everyone. Elevate your travel plans with a trip to Ashland and immerse yourself in its diverse offerings.

Download Your Ashland Travel Checklist

Planning your trip to Ashland just got easier! We’ve created a handy, printable checklist featuring all 21 must-do activities to ensure you make the most of your visit.

📄 Click here to download your Ashland Travel Checklist

Whether you’re exploring Lithia Park, savoring chocolates at Branson’s, or catching a show at the Oregon Shakespeare Festival, this checklist will help you stay organized and inspired. Print it out, check off each experience, and make your Ashland adventure truly unforgettable!

(Tip: Keep it on your phone or tablet for easy access while you explore!)