17 Best Things To Do In Ashland, Oregon

Ashland, Oregon is the kind of place that surprises you—in all the best ways. One moment you’re wandering through art galleries and grabbing espresso downtown, the next you’re catching a Shakespeare play, hiking mountain trails, or sipping Pinot Noir with a vineyard view.

This 2025 guide covers 17 amazing things to do in Ashland, from big-name favorites like the Oregon Shakespeare Festival and Lithia Park to cool local finds like First Friday Art Walk, mineral soaks, river rafting, and family-friendly museums. These aren’t just tourist stops—they’re active, open, and loved by locals right now.

Ashland blends culture, nature, and laid-back charm like few places can. The food scene? Creative and locally driven. The outdoor access? Instant. The vibe? Friendly, artistic, and full of energy. If you’re looking for where to go, what to see, and what not to miss in Ashland, start here.

This is your inside track to exploring one of Oregon’s most dynamic small towns.

1. Oregon Shakespeare Festival (OSF)

Address: 15 S Pioneer St, Ashland, OR 97520

The Oregon Shakespeare Festival is not just a theater—it’s the beating heart of Ashland’s cultural identity. Founded in 1935, OSF has evolved into one of the most respected repertory theater companies in the country, offering a compelling mix of Shakespearean classics, new works, and musicals. Each season spans from March through October and includes performances across three distinct venues: the outdoor Allen Elizabethan Theatre, the intimate Thomas Theatre, and the architecturally striking Angus Bowmer Theatre.

Walking into OSF is like stepping into a world of dramatic storytelling, community energy, and meticulous artistry. Whether you're a seasoned theatergoer or attending your first live show, the festival’s quality and passion are undeniable. Add in the pre-show Green Show (a free outdoor performance) and you’ve got an unforgettable night of entertainment under the Oregon sky.

2. Lithia Park

Address: 59 Winburn Way, Ashland, OR 97520

Lithia Park is Ashland’s natural jewel—a 100-acre expanse of gardens, wooded trails, and meandering creeks nestled along Ashland Creek. Designed in 1914 by a student of Frederick Law Olmsted (the architect behind New York’s Central Park), Lithia Park offers an immersive blend of cultivated beauty and untamed Oregon wilderness.

Stroll past rhododendrons, Japanese maples, and serene duck ponds. Pause at the rose garden or the picturesque bandshell where local musicians often perform. Families gather at the playgrounds and grassy lawns, while couples find quiet corners for picnics or reading under the trees. The park connects directly to downtown, making it the perfect pause between shopping, dining, or a theater performance.

Whether you're jogging, birdwatching, or simply unwinding, Lithia Park invites you to slow down and connect with nature in the heart of the city.

3. Downtown Ashland

Address: Centered around Main St & Lithia Way, Ashland, OR 97520

Downtown Ashland is a vibrant, walkable mix of historic charm and contemporary creativity. Cobblestone-like sidewalks guide visitors past locally owned boutiques, bookstores, and galleries, many housed in lovingly preserved 19th-century buildings. You’ll find everything from fine art and handmade jewelry to quirky gifts and outdoor gear.

Cafés buzz with conversation, and outdoor patios brim with diners sampling regional wines or seasonal farm-to-table fare. Street performers and pop-up artists animate the atmosphere, especially during summer weekends when the town hums with OSF audiences and day-trippers alike.

This downtown isn’t just a place to shop—it’s a social, artistic, and cultural crossroads where creativity and community shine year-round.

4. Oregon Cabaret Theatre

Address: 241 Hargadine St, Ashland, OR 97520

Perched on a hill in a beautifully restored 1911 church, the Oregon Cabaret Theatre brings Broadway-quality entertainment to a cozy, intimate stage. Known for its professional musicals, comedies, and revues, this venue delivers theatrical magic with a side of excellent cuisine. With seating for just over 100 guests, every seat feels close to the action, and the ambiance strikes a perfect balance between vintage charm and theatrical flair.

Dining here is part of the experience. Think artisan cocktails, locally sourced dishes, and decadent desserts—all served before and during the performance. The Cabaret's seasonal productions keep the repertoire fresh and engaging, drawing repeat audiences year after year.

5. Schneider Museum of Art

Address: 1250 Siskiyou Blvd, Ashland, OR 97520 (on SOU campus)

Ashland may be famous for theater, but its visual arts scene is just as captivating. At the Schneider Museum of Art, visitors find an inspiring mix of contemporary exhibitions, experimental works, and regional talent, all housed within a light-filled modern space on the Southern Oregon University campus.

The museum focuses on thought-provoking themes and frequently spotlights underrepresented voices, making each visit feel fresh and intellectually stimulating. You'll encounter installations, sculptures, paintings, and mixed media pieces that challenge perception and invite discussion. Their Art Beyond campus initiative also places art throughout SOU and the greater Rogue Valley.

This is a great stop for art lovers, students, and anyone seeking a more reflective side of Ashland’s creative identity.

6. ScienceWorks Hands-On Museum

Address: 1500 E Main St, Ashland, OR 97520

Perfect for families, curious minds, and science geeks of all ages, ScienceWorks is a beloved hands-on museum packed with interactive exhibits that make learning fun. The museum features everything from physics-based challenges and engineering puzzles to biology stations and rotating seasonal displays.

Young visitors can launch rockets, play with kinetic sculptures, explore sensory tables, and even dig for fossils. Meanwhile, adults often find themselves just as engaged—especially with the science demonstrations and "Maker Lab" workshops. The outdoor Discovery Garden adds a nature twist with butterfly-friendly plants, interactive water features, and plenty of room to roam.

This spot is more than a museum—it’s a playground for the mind.

7. Mount Ashland Ski Area

Address: 11 Mt Ashland Ski Rd, Ashland, OR 97520

Perched 7,500 feet above the Rogue Valley floor, Mount Ashland delivers classic Pacific-Northwest skiing with a delightfully down-to-earth vibe. Four chairlifts fan out from the cozy mid-mountain lodge, unlocking 240 acres of terrain that ranges from gentle learning slopes to the double-black chutes of The Bowl. Clear days treat you to jaw-dropping views of Mount Shasta, while storm cycles bury the upper mountain in silky, blower powder. Inside the timber-framed lodge, a crackling fireplace, local microbrews, and famous nachos keep the après scene friendly and unpretentious. Off-season, the ski road transforms into a gateway for wildflower hikes, disc-golf tournaments, and gravity-fed mountain-bike races, making “Mount A” a four-season playground just 25 minutes from downtown Ashland.

8. Rogue River Rafting (Noah’s River Adventures)

Address: 53 N Main St, Ashland, OR 97520

Ashland’s theatre crowds by night become white-water warriors by day thanks to the legendary Rogue River, a federally designated Wild & Scenic waterway just 45 minutes west of town. Outfitters like Noah’s River Adventures supply everything—rafts, paddles, gourmet riverside lunches, and guides who can spot an osprey nest at 100 yards. Trips range from gentle family floats through swooping canyons to adrenaline-laden descents of Rainie Falls and Blossom Bar. Between rapids you’ll drift past mossy cliffs, swimming holes, and the occasional black-bear cub foraging on shore. For multi-day expeditions, guides prepare Dutch-oven dinners under star-splashed skies and share tales of Zane Grey and Native Takelma lore. Whether you choose a mellow scenic float or a bucket-list wilderness trip, Rogue rafting adds a splash of untamed Oregon to any Ashland visit.

9. Emigrant Lake County Park

Address: 5505 Highway 66, Ashland, OR 97520

Only six miles southeast of town, Emigrant Lake is Ashland’s aquatic playground, ringed by volcanic hills that glow gold at sunset. Summer days invite paddle-boarders gliding across glassy water, anglers casting for bass and trout, and families zipping down the twin 280-foot waterslides that curve into a turquoise plunge pool. Shore-side picnic shelters sit beneath towering black oaks, while a 42-site campground lets you swap city lights for Milky-Way stargazing.

In cooler months, the 3-mile East Lake Trail offers breezy hikes with panoramic views of Pilot Rock and snow-capped Siskiyous. Whether you’re launching a kayak at dawn or grilling burgers while kids skip stones, Emigrant Lake blends classic lake-day fun with Southern Oregon scenery that begs for a camera.

10. Irvine & Roberts Vineyards

Address: 1614 Emigrant Creek Rd, Ashland, OR 97520

Set atop rolling hills just 10 minutes from downtown, Irvine & Roberts Vineyards is a gem in Southern Oregon’s wine scene, known for cool-climate varietals like Pinot Noir and Chardonnay. The moment you step onto their terraced patio, expansive views of the Rogue Valley set the tone for an elegant yet approachable tasting experience. Inside, the modern tasting room pairs warm hospitality with artfully plated charcuterie boards and limited-production wines sourced from estate vines rooted in ancient marine soils.

This is a place where time slows down and every sip feels meaningful. Whether you’re a wine connoisseur or casual visitor, the guided tastings here are curated to educate and elevate. Friendly staff walk you through each vintage’s nuances, revealing how the vineyard’s elevation and ocean breezes shape every pour.

11. Belle Fiore Estate Winery

Address: 100 Belle Fiore Ln, Ashland, OR 97520

Belle Fiore feels like a slice of Europe transplanted to the Oregon hills. This stately French-and-Italian inspired estate rises above the valley like a Tuscan villa, complete with manicured gardens, arched verandas, and a grand tasting room that wouldn’t look out of place in Bordeaux. But the magic isn’t just in the setting—it’s in the bottle.

Wines here range from Rhône-style reds and bold Cabernets to rare estate-grown Viognier, all crafted with precision and flair. Tastings can be as relaxed or refined as you wish—choose the cozy Library Room for fireside sips or the Vista Terrace for sweeping mountain views. Belle Fiore also hosts a calendar of upscale culinary events, blending fine wine with food, art, and live music.

12. Weisinger Family Winery

Address: 3150 Siskiyou Blvd, Ashland, OR 97520

Family-owned and deeply rooted in the local soil, Weisinger Family Winery offers an intimate and authentic tasting experience that balances sophistication with warmth. Located just south of town near the Cascade foothills, the winery’s low-slung tasting room is surrounded by vine-covered slopes and wildflower meadows, creating a laid-back vibe ideal for unwinding.

Weisinger specializes in small-batch wines crafted from estate and neighboring vineyards, with a focus on Tempranillo, Syrah, and Viognier. You’ll often find a Weisinger pouring the flights themselves, eager to share stories about the land, the harvest, and their journey. The shaded deck invites lingering, while inside, rustic beams and soft jazz complete the relaxed elegance.

13. Ashland Independent Film Festival (AIFF)

Address: Screenings primarily at Varsity Theatre, 166 E Main St, Ashland, OR 97520

Every April, Ashland transforms into a cinematic hotspot during the Ashland Independent Film Festival. For five days, the town buzzes with filmmakers, movie lovers, and curious locals united by a shared love for storytelling. The festival showcases over 100 films, from short documentaries and animation to international feature-length narratives—all carefully curated for quality and impact.

AIFF isn't just about screenings; it's an immersive cultural event. Attendees mingle at rooftop receptions, attend panel discussions, and engage with directors in intimate settings that foster meaningful dialogue. The Varsity Theatre anchors the experience, but venues across town—like the Historic Armory and Ashland Springs Hotel—extend the cinematic atmosphere.

14. First Friday Art Walk

Address: Throughout downtown Ashland, especially on Main St and A St.

On the first Friday of every month, Ashland’s creative energy spills into the streets during the First Friday Art Walk. This beloved local tradition invites residents and visitors alike to explore the town’s vibrant gallery scene. From emerging artists to established talents, the evening is a showcase of visual art in all its forms—painting, ceramics, sculpture, photography, and more.

What sets Ashland’s art walk apart is the atmosphere: open studio doors, wine and cheese receptions, live acoustic music, and artists eager to chat about their process. Many downtown shops and cafes stay open late and join the fun, offering discounts or hosting pop-up exhibits.

It’s a relaxed, uplifting way to experience Ashland’s community spirit while supporting local creatives.

15. Lithia Springs Resort

Address: 2165 W Jackson Rd, Ashland, OR 97520

For those craving rejuvenation, Lithia Springs Resort offers a serene retreat just minutes from downtown. Known for its healing mineral waters, the resort invites guests to unwind in clawfoot tubs filled with the same fizzy, iron-rich spring water that once put Ashland on the map. Lush gardens, koi ponds, and vine-covered pergolas set the stage for a restful escape.

Accommodations range from modern suites to romantic cottages, each thoughtfully appointed with plush robes, fireplaces, and local artwork. Mornings start with a complimentary organic breakfast, and afternoons are made for lounging with a glass of wine from the nearby Rogue Valley vineyards. The on-site spa offers massage, facials, and aromatherapy—all ideal for unwinding after a day of hiking, skiing, or theatergoing.

16. Crater Lake National Park (Day Trip from Ashland)

Address: Crater Lake National Park, Rim Dr, Crater Lake, OR 97604

No trip to Southern Oregon is complete without a day trip to Crater Lake National Park—home to the deepest, clearest lake in the United States and one of the most awe-inspiring sights in the Pacific Northwest. Formed over 7,000 years ago from a collapsed volcano, the lake’s intense blue color, framed by sheer caldera walls and evergreen forests, is unforgettable.

From Ashland, the scenic drive to the park is a journey in itself, passing rivers, pine forests, and small alpine towns. Once inside, you can explore Rim Drive (usually open July–October), which offers 33 miles of dramatic viewpoints, hiking trailheads, and picnic stops. Popular hikes include Garfield Peak, Watchman Overlook, and Cleetwood Cove Trail—the only legal lake access where daring visitors can take a dip in the icy waters.

17. Ashland Dining Scene

Address: Concentrated along Main St, Lithia Way, and A St.

Ashland’s culinary offerings are as vibrant as its arts scene, with flavors that reflect both regional bounty and global inspiration. Whether you’re indulging in a nine-course tasting menu or grabbing farm-fresh tacos from a food truck, dining here is part of the adventure.

Fine dining shines at MÄS, where Chef Josh Dorcak offers Japanese-Peruvian fusion with a hyper-local, foraged twist—think matsutake mushrooms, steelhead roe, and kombu broth. For a romantic meal, Peerless Restaurant & Bar combines candlelit ambiance with seasonal Pacific Northwest fare and an excellent wine list. Breakfast lovers swear by Morning Glory, a cozy spot near the university serving legendary scrambles and house-baked muffins.

Casual options abound too: Brickroom for gastropub vibes and craft cocktails, Martolli’s for pizza that hits the spot, and Larks at Ashland Springs Hotel for refined regional comfort food.

Conclusion

Ashland is the kind of place that surprises you with how much there is to see and do. Whether you’re a theater buff looking to dive into the magic of the Oregon Shakespeare Festival or an outdoor adventurer ready to explore the beautiful trails around town, there’s no shortage of things to do in Ashland. You can spend your days sipping local wine at picturesque vineyards, hiking through scenic parks, or even stargazing under some of the clearest skies in Oregon.

From charming restaurants and hidden art galleries to family-friendly spots like ScienceWorks Hands-On Museum, Ashland offers a little something for everyone. It's a town where culture meets nature, and where every turn invites you to slow down, enjoy the moment, and discover something new. So, whether you’re here for a weekend or an extended stay, you’re bound to find plenty of fun and memorable things to do in Ashland!

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FAQ

1. Where can I find a secret garden to unwind in Ashland?

Lithia Park is well-known, but many visitors miss the secluded Japanese-style garden near the upper duck pond. It's a peaceful spot perfect for reflection and a break from the bustle.

2. Ashland is famous for its Shakespeare Festival, but are there any unconventional theatre experiences here?

Outside of the Oregon Shakespeare Festival, Ashland offers immersive theater experiences through the Ashland New Plays Festival and interactive performances at smaller venues like the Cabaret Theatre. These provide a more intimate setting and innovative storytelling techniques.

3. I love outdoor adventures. What’s an unusual outdoor activity to try in Ashland, OR?

For a unique outdoor experience, try nighttime stargazing hikes organized by local astronomy clubs. The clear skies in Ashland’s surrounding areas offer breathtaking views of the stars.

4. Can I experience any unique local foods or drinks in Ashland, OR?

Absolutely! Beyond the typical fare, Ashland has a burgeoning craft cider scene. Local orchards offer tastings and tours, where you can learn about cider production and sample unique blends.

5. Are there any hidden art spots in Ashland?

Yes, aside from the well-known galleries, there are several hidden art spots around town. Keep an eye out for alleyways and courtyards in the downtown area, which often host pop-up art installations and guerrilla art shows.

6. What’s the best way to experience Ashland’s natural beauty without crowds?

The Oredson-Todd Woods trail is a less-traveled path that offers serene forest walks and views of the city from a different perspective, away from the more popular trails.

7. Is there a place in Ashland where I can learn about local folklore and legends?

The Southern Oregon Historical Society occasionally offers tours and talks focusing on local lore, including tales of early settlers, indigenous stories, and Ashland’s ghost legends.