Name: Arlington Club: Ashland Oregon Shakespeare Festival (OSF)
Start: 2026-06-09T00:00:00.000Z
End: 2026-06-13T00:00:00.000Z
Location: Ashland, Oregon

InquisiTours

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Jun 9 - 13, 2026

Group size: 8 - 12

Arlington Club: Ashland Oregon Shakespeare Festival (OSF)

Ashland, Oregon

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InquisiTours

Email address verified

Jun 9 - 13, 2026

Group size: 8 - 12

Accommodations
Boutique lodging at Winchester Inn B&B. Combining rich history and luxury. Off street parking is located behind and alongside the property.
OSF Insider Access
Exclusive speakers, tours, and actor meetings as arranged by Arlington Club member, Mary Wilcox.
Daily Breakfast
Welcome Dinner: Reserved
We’ve secured tables at Alchemy Restaurant & Bar, named one of OpenTable’s Top 100 Restaurants for Foodies in America. Reservation is included; food & beverages are on your own.
Farewell dinner
Farewell dinner at Larks Home Kitchen Cuisine—the Ashland Springs Hotel’s award-winning, farm-to-table restaurant.

Two people - Room with Queen Bed

Deposit: $1,215

Available until November 1, 2025Sold Out

$2,425

Deposit: $1,215

Two people - Room with King Bed

Deposit: $1,240

Available until November 1, 2025Sold Out

$2,475

Deposit: $1,240

Two people - Suite - Queen

Deposit: $1,550

Available until November 1, 2025Only 1 left

$3,100

Deposit: $1,550

Two people - Suite - King

Deposit: $1,575

Available until November 1, 20254 left

$3,150

Deposit: $1,575

Single - Suite - Queen

Deposit: $1,325

Available until November 1, 2025Only 2 left

$2,650

Deposit: $1,325

Two people - Two Bedroom Suite

Deposit: $1,750

Available until November 1, 2025Sold Out

$3,500

Deposit: $1,750

Day 1 - June 9
Day 1 - June 9
Arrival Day - Welcome to Ashland!
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.
5:30 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.

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

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Day 2 - June 10
Day 2 - June 10
Explore & Experience Ashland
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
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Day 3 - June 11
Day 3 - June 11
Your Day, Your Way: Optional Jacksonville Excursion
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
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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

How to join: Please indicate your interest in the Jacksonville option at checkout so we can confirm capacities and follow up with pricing and final details.

Note: The Jacksonville excursion overlaps with the both matinee and evening performances.
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Day 4 - June 12
Day 4 - June 12
Final Day in Ashland
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
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Day 5 - June 13
Day 5 - June 13
Departure Day – Farewell Ashland
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!
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