Ashland + the Oregon Shakespeare Festival: Your Perfect Blend of Stage and Play

Experience world-class theater and the best of Ashland at your own pace. We’ve designed this trip to balance shared moments with plenty of your own time so you can savor great performances and also wander, sip, stroll, soak, and explore.

Discover the power of live performance at the Oregon Shakespeare Festival—one of the nation’s leading nonprofit theatres and a cherished cultural destination since 1935. Located in the charming town of Ashland, OSF presents a dynamic season of plays and musicals in rotating repertory, blending bold new works with fresh takes on Shakespeare and timeless classics. With productions that have graced Broadway stages and captivated audiences worldwide, we invite you to experience theatre that reveals our shared humanity, sparks conversation, and inspires generations.

Our home base is the Arlington Club group room block at The Winchester Inn—an easy, walkable launch pad to the OSF campus, the Plaza, Lithia Park, cafés, galleries, shops, and more. To make the most of your downtime, we’ve included a list of popular ways to enjoy Ashland and the surrounding area (think guided walks, spa time, biking, hikes, tastings, and day trips). Pick what delights you—this getaway is as flexible as you are.

What’s included
Boutique lodging at The Winchester Inn B&B (steps from the theaters), a farewell dinner at Larks, and our OSF Insider Access—a board-assisted suite of private tours and guest conversations with OSF artists and leadership for exclusive behind-the-scenes insight (with thanks to Mary Wilcox). Experiences are curated for our group and scheduled around OSF availability.

For guests registering after January 26:

Your program now includes a half-day experience in Jacksonville, followed by a special evening at Three B’s Ranch, owned by Arlington Club member Dan Belica on day 3, June 11.

What’s not included
OSF performance tickets. Guests purchase tickets directly for their preferred dates, times, and seating. We’ll share timely reminders and links when sales open.

Payment, Cancellation & Change Policy

Payment Schedule

• Pricing shown is per room based on double or single occupancy

• There are several different room types - please choose accordingly

• At booking: 50% of total (hotel prepayment). A one-time $175 per-person administrative/planning fee applies at this time.

• March 25, 2026: Remaining balance due.

Reservations are confirmed once the initial 50% prepayment and administrative details are completed.

Full Cancellations

• 60+ days before arrival: Hotel prepayment refundable, less a 50% handling fee.

• Inside 60 days of arrival: Full hotel prepayment is non-refundable.

Partial Cancellations (e.g., dropping one or more nights)

• 60+ days before arrival: A 20% fee applies to any canceled night(s).

• Inside 60 days of arrival: The cost of any dropped night(s) is non-refundable.

Additional Terms

• The $175 administrative/planning fee (per person) is non-refundable.

• Please confirm travel dates before booking to avoid fees.

• We strongly recommend travel insurance to protect your investment.

Payment Methods

• Credit cards incur a 3.0%–3.9% processing charge (varies by card).

• ACH payments are available and do not incur processing charges, however, there is a small "service charge" for using online registration.

• Avoid all fees by paying by checks. Include “Arlington Club” in the memo and mail to:
  InquisiTours
  933 University Street
  Walla Walla, WA 99362

History & Legacy 

The Oregon Shakespeare Festival (OSF) was founded in 1935 by Angus L. Bowmer, a local drama teacher with an ambitious vision: to bring Shakespeare’s plays to life in a small town in southern Oregon. That first summer, audiences gathered in a makeshift Elizabethan-style theatre built from the remains of an old Chautauqua building to see Twelfth Night and The Merchant of Venice. What began as two performances with a shoestring budget grew steadily, interrupted only during World War II, and soon became a cultural cornerstone in Ashland. 

The Elizabethan Theatre, central to OSF’s identity, has evolved alongside the festival. The first open-air stage was constructed in 1935 on the Chautauqua site, rebuilt after a fire in 1940, and then redesigned in 1959 into the larger Allen Elizabethan Theatre seen today. In 1992, the theatre gained a protective roof structure and modernized facilities, improving both comfort and acoustics while preserving its Elizabethan character. The venue remains the largest of OSF’s stages and the heart of its summer season. 

Over the decades, OSF expanded far beyond its modest beginnings. New theatres were added, including the indoor Angus Bowmer Theatre in 1970 and the Thomas Theatre in 2002, creating spaces for a wide range of productions—from Shakespeare to contemporary works and world premieres. In 1958, OSF became the first theatre in the United States to complete Shakespeare’s entire canon, a milestone it has since achieved several times. In recognition of its artistic excellence, OSF received the Regional Theatre Tony Award in 1983. 

Today, OSF presents more than 800 performances annually across three theatres, welcoming nearly 400,000 visitors each season. It is one of the largest and longest-running professional nonprofit theatres in the country. Through its innovative rotating repertory model, OSF has influenced regional theatres nationwide and become a leader in new play development, commissioning and premiering works that have gone on to stages across the U.S. 

The impact of OSF reaches far beyond its stages. The festival has transformed Ashland into a destination for the arts, driving cultural and economic vitality in the region. Its commitment to equity, diversity, and inclusion has also reshaped the field of American theatre, broadening whose stories are told and who gets to tell them. 

Nearly ninety years after its founding, OSF continues to honor its roots in Shakespeare while championing new voices, proving that live theatre has the power to inspire, challenge, and connect us all.

OSF Performance Time Slots

Use this list when selecting tickets (locations included for reference).

Tuesday, June 9, 2026
8:00 PM – Dream — Bowmer Theatre
8:00 PM – Cordially — Thomas Theatre

Wednesday, June 10, 2026
1:30 PM – Dream — Bowmer Theatre
1:30 PM – Cordially — Thomas Theatre
8:00 PM – Come From Away — Bowmer Theatre

Thursday, June 11, 2026*
1:30 PM – Come From Away — Bowmer Theatre
8:00 PM – Raisin — Bowmer Theatre
8:00 PM – Cordially — Thomas Theatre

*If you’re interested in joining the Jacksonville afternoon + dinner, skip Thursday’s 1:30 PM and 8:00 PM tickets.
If are interested in only dinner, skip the evening performance.

Friday, June 12, 2026
1:30 PM – Raisin — Bowmer Theatre
1:30 PM – Cordially — Thomas Theatre
8:00 PM – The Shrew — Elizabethan Theatre (Preview)
8:00 PM – Dream — Bowmer Theatre

Saturday, June 13, 2026
1:30 PM – Dream — Bowmer Theatre
1:30 PM – Cordially — Thomas Theatre

Some experiences require advance reservations—please plan ahead.

Guided Nature & City Tours

• Lithia Park – guided stroll through Ashland’s crown-jewel green space: ashlandoregon.gov/facilities/Lithia-Park

• Ashland Japanese Garden (in Lithia Park) – serene self-guided visit (open daily, seasonal hours): ashlandjapanesegarden.org

• Downtown Ashland shopping & browsing – boutiques, galleries, cafés: travelashland.com/shopping

• Walk Ashland (Peter Finkle) – themed walking tours (Lithia Park, Downtown, Haunted Ashland & more): walkashland.com • Book: walkashland.setmore.com

Wine Tours of Southern Oregon

• Bravo Outings: https://bravooutings.com/

Outdoor Adventures

• Bike Ride: Ashland → Jacksonville : BIKE ROUTE: https://www.komoot.com/smarttour/e1387340944/jacksonville-loop-via-bear-creek-greenway-ashland

  • Bring your own bike or E-bike rentals: Piccadilly Cycles (Railroad District): piccadillycycles.com

• Whitewater Rafting – half- or full-day on the Upper Klamath or Rogue:

  • Momentum River Expeditions: momentumriverexpeditions.com

  • Noah’s River Adventures: noahsrafting.com

  • Indigo Creek Outfitters: indigocreekoutfitters.com

• Hiking – from easy park paths to Cascade vistas:

  • Ashland Woodland & Trails Association (trail info): ashlandtrails.org

  • Ashland Map Guide (15,000-acre watershed maps): travelashland.com/ashland-map-guide

  • Grizzly Peak (BLM overview): blm.gov/visit/grizzly-peak-trail

  • PCT access (Mt. Ashland / Grouse Gap): USFS notes: fs.usda.gov/r05/klamath/recreation/trails/mt-ashland-area-pacific-crest-trail • PCTA trailhead: explore.pcta.org/trailheads/grouse-gap-trailhead

• Day Trip: Crater Lake National Park – ~2 hours each way through the Cascades to an iconic caldera lake:

  • Park info: nps.gov/crla • Current conditions: nps.gov/crla/planyourvisit/conditions.htm

Spas & Soaking

• Chozu Bath & Tea Gardens – outdoor soaking pools, steam, sauna: chozugardens.com

• Blue Giraffe Day Spa – massage, facials, nails & more: bluegiraffespa.com

• Waterstone Spa – downtown & Lithia Springs locations: waterstonespa.com

We strongly encourage all travelers to purchase travel insurance to protect your trip investment. Coverage should include trip interruption, medical care, baggage protection, and cancellation due to unforeseen events. While InquisiTours does not sell insurance directly, we recommend looking into providers such as Travel Safe or Faye Travel Insurance for comprehensive policies.

For additional peace of mind, we also recommend MedJet Horizon for emergency medical evacuation and travel security coverage when traveling more than 150 miles from home.

We suggest purchasing coverage at the time of booking to ensure eligibility for the most complete benefits. Please read all policy documents carefully and select a plan that aligns with your personal health and travel needs.

4:00 PM – Individual Arrival & Group Check-In
Welcome to Ashland! Upon arrival, please check in at our preferred bed and breakfast: Winchester Inn
A boutique gem in the heart of Ashland, the Winchester Inn offers elegant accommodations and warm hospitality. It will serve as your base for this memorable theater getaway.

5:00 PM – Welcome Group Dinner
Alchemy Restaurant at the Winchester Inn
Join us for a welcome dinner at Alchemy, one of Ashland’s most acclaimed dining experiences—located right at the Inn. (Dinner to be paid individually on-site)

OSF Insider:
An Oregon Shakespeare Festival (OSF) Leader or Artist will join us for dinner to offer personal insight into the season and productions. (Topic and guest TBD)

8:00 PM – Evening Performance at OSF - TICKETS TO BE PURCHASED ON YOUR OWN, starting on NOVEMBER 4.*

• Evening play options:

  • A Midsummer Night's Dream (Angus Bowmer Theatre)

  • You Are Cordially Invited to the End of the World! (Thomas Theatre)

*For more information on the 2026 season performances, visit: https://www.osfashland.org/en/news-multimedia/news-announcements/2026-season-announcment.aspx

Breakfast at The Winchester Inn (included)

Morning — pick one

• Free time & optional activities: see “Free Day Ideas” (guided walks, spas, hiking, shopping, biking, etc.), or

• 10:00 AM — Inside OSF: Member Backstage Tour (private for Arlington Club members; at “The Bricks”)

12:00 PM — Lunch on your own

• Explore Ashland’s cafés and bistros at your leisure.

1:30 PM — Optional OSF matinee (on your own)*

• A Midsummer Night’s Dream — Angus Bowmer Theatre

• You Are Cordially Invited to the End of the World! — Thomas Theatre

4:15 PM — Inside OSF: Set-Change Experience

• Watch the transformation from A Midsummer Night’s Dream to Come From Away.

Evening — Dinner on your own

• Seeing an evening show? Aim for 5:15–5:45 PM reservations.

• Not attending? Better availability after 7:30 PM.

8:00 PM — Optional OSF evening performance (on your own)*

• Come From Away — Angus Bowmer Theatre

*Tickets are purchased directly by guests and are expected to be available after November 4, 2025. 2026 season info: https://www.osfashland.org/en/news-multimedia/news-announcements/2026-season-announcment.aspx

Breakfast at The Winchester Inn (included)

Option A — OSF Day

• Morning — Free time & optional activities
  See “Free Day Ideas” (guided walks, spas, hiking, shopping, biking, etc.).

• 12:00 PM — Lunch on your own
  Explore Ashland’s cafés and bistros.

  1:30 PM — Optional OSF matinee (on your own)

  • Come From Away — Angus Bowmer Theatre

• Evening — Dinner on your own

  • Seeing a show? Aim for 5:15–5:45 PM reservations.

  • Not attending? Better availability after 7:30 PM.

• 8:00 PM — Optional OSF evening performance (on your own)

  • A Raisin in the Sun — Angus Bowmer Theatre

  • You Are Cordially Invited to the End of the World! — Thomas Theatre

Tickets are purchased directly by guests and are expected to be available after November 4, 2025. 2026 season info: https://www.osfashland.org/en/news-multimedia/news-announcements/2026-season-announcment.aspx

__________________________________________________

For guests registering after January 26:

Your program includes a half-day experience in Jacksonville, followed by a special evening at Three B’s Ranch, owned by Arlington Club member Dan Belica on day 3, June 11.

Option B — Jacksonville Afternoon & Ranch Dinner (interest-gathering)

• 12:30–1:00 PM — Pickup at The Winchester Inn (Ashland) → private transfer to Jacksonville

• Jacksonville highlights

  • Guided stroll through the historic district

  • Trolley ride (as available)

  • Group winery tasting (to be confirmed)

• 5:30 PM — Cocktails & catered dinner at Arlington Club member Dan Belica's Three B's Ranch

• ~8:30 PM — Return to Ashland
  Drop-off at The Winchester Inn

  
  
  Note: The Jacksonville excursion overlaps with the both matinee and evening performances.

Breakfast at The Winchester Inn (included)

Morning — pick one

• Free time & optional activities
  See “Free Day Ideas” (guided walks, spas, hiking, shopping, biking, etc.), or

• 10:00 AM — Inside OSF: Production Building Tour (private for Arlington Club Members)
  Location: 408 Talent Ave, Talent, OR (≈15-minute drive from The Winchester Inn)
  Note: You’ll need a car/rideshare or to carpool for this experience.

12:00 PM — Lunch on your own
Explore Ashland’s cafés and bistros.

1:30 PM — Optional OSF matinee (on your own)

• A Raisin in the Sun — Angus Bowmer Theatre

• You Are Cordially Invited to the End of the World! — Thomas Theatre

4:15 PM — Inside OSF: Post-show Talkback
Following A Raisin in the Sun.

5:30 PM — Farewell Group Dinner at Larks
Gather for a celebratory final meal at Larks Home Kitchen
Guest speaker: OSF Insider (artist or leader) offering behind-the-scenes insights. (TBD)

8:00 PM — Optional OSF evening performance (on your own)

• The Taming of the Shrew — Allen Elizabethan Theatre

• A Midsummer Night’s Dream — Angus Bowmer Theatre

Tickets are purchased directly by guests and are expected to be available after November 4, 2025. 2026 season info: https://www.osfashland.org/en/news-multimedia/news-announcements/2026-season-announcment.aspx

10:00 AM — OSF Insider Coffee Chat (Bowmer Lobby)
Exclusive for Arlington Club members.

By 11:00 AM — Check out of The Winchester Inn
If you need luggage storage, please inquire at the front desk.

Choose your own wrap-up

• Head home at your leisure, or

• 1:30 PM — Optional OSF Matinee (on your own):

  • A Midsummer Night’s Dream (Angus Bowmer Theatre)

  • You Are Cordially Invited to the End of the World! (Thomas Theatre)
    

OSF Tickets are purchased directly by guests and are expected to be available after November 4, 2025. 2026 season info: https://www.osfashland.org/en/news-multimedia/news-announcements/2026-season-announcment.aspx

Thank you for joining us in Ashland. We hope you leave with lasting memories, new connections, and a renewed appreciation for the arts and culture of Southern Oregon. Safe travels!