Ashland Shakespeare Festival: 5-Day Theater & Culture Tour

Introduction

Ashland Shakespeare Festival / September 9-13, 2026

Ashland Shakespeare Festival: 5-Day Theater & Culture Tour

Immerse yourself in the magic of live theater, charming streets, and Southern Oregon’s scenic beauty on this carefully paced journey to Ashland. With multiple Oregon Shakespeare Festival performances, behind-the-scenes access, wine tasting, and ample free time, this tour blends culture, comfort, and unforgettable storytelling.

Tour Pricing

Solo Traveler: $3499

Double - per traveler: $2899

$250 Deposit due upon booking

Final Payment due: July 10th, 2026

Festival Highlights

At a glance

Ashland Shakespeare Festival: 5-Day Theater & Culture Tour

Tour Pricing

Map

Day 1 - Journey South & Opening Night

Travel to Ashland and Festival Opening Night

Journey South through Oregon

Sit back and relax as we travel south through scenic Oregon, enjoying a delightful included lunch along the way. Upon arrival in Ashland, we check into the historic Ashland Springs Hotel and settle in before stepping into the world of Shakespeare.

Lunch

Enjoy a delightful included lunch along the way as you travel south through Oregon.

Ashland Springs Hotel

Upon arrival in Ashland, check into your hotel and settle in before the evening's activities.

Pre-show Lecture

This evening begins with a pre-show lecture, offering context and insight that enhances tonight’s performance.

Dinner

Enjoy dinner together before the evening performance.

Henry IV at Allen Elizabethan Theatre

Take your seats at the iconic Allen Elizabethan Theatre for Henry IV, opening the festival experience beneath the stars.

Day 2 - Discover Ashland & Evening Performance

Guided Walking Tour and Emma Performance

Breakfast

Enjoy breakfast before starting your day in Ashland.

Guided Walking Tour of Ashland

Enjoy a guided walking tour of Ashland, led by a knowledgeable local guide who brings the town’s history, architecture, and artistic spirit to life.

Afternoon Free Time

The afternoon is yours to explore at your own pace—browse bookstores, stroll along Lithia Creek, or relax in Lithia Park.

Pre-show Talk

This evening includes another engaging pre-show talk before the performance.

Dinner

Enjoy dinner before the evening performance.

Emma at Allen Elizabethan Theatre

Attend a captivating performance of Emma at the Allen Elizabethan Theatre.

Day 3 - Behind the Curtain

Exclusive Backstage Tour and Evening Show

Breakfast

Enjoy a leisurely morning before going behind the scenes at the Oregon Shakespeare Festival.

Behind the Curtain Tour at Oregon Shakespeare Festival

This exclusive Behind the Curtain Tour offers a fascinating look at costume shops, rehearsal spaces, and the artistry that brings each production to life.

Afternoon in Downtown Ashland

Spend the afternoon enjoying downtown Ashland before regrouping for the evening.

Pre-show Lecture

Regroup for a pre-show lecture before dinner and the evening performance.

Dinner

Enjoy dinner before the evening performance.

The Taming of the Shrew at Allen Elizabethan Theatre

Attend an evening performance of The Taming of the Shrew, another festival highlight in the Allen Elizabethan Theatre.

Day 4 - Festival Campus, Wine & Broadway-Style Theater

Campus Tour, Wine Tasting, and Broadway Musical

Breakfast

After breakfast, we explore more of the festival with a guided campus tour, learning about the history and scale of one of the nation’s premier repertory theaters.

Guided Festival Campus Tour

Explore more of the festival with a guided campus tour, learning about the history and scale of one of the nation’s premier repertory theaters.

Wine Tasting at Local Vineyard

Midday brings a relaxed wine tasting and lunch at a local vineyard before returning to Ashland for free time.

Lunch at Local Vineyard

Enjoy lunch at a local vineyard before returning to Ashland for free time.

Afternoon Free Time in Ashland

Return to Ashland for free time before regrouping for dinner and the evening performance.

Dinner

This evening, we enjoy dinner together before attending the musical.

Come From Away at Angus Bowmer Theatre

Attend Come From Away at the Angus Bowmer Theatre, a powerful and uplifting musical that perfectly complements our classical performances.

Day 5 - Farewell to Ashland and Final Vineyard

Final Vineyard Tasting and Journey Home

Breakfast

Breakfast is at the Historic Ashland Springs Hotel followed by free time and a relaxing morning prior to leaving Ashland.

Depart Ashland and Travel North

Following breakfast, we depart Ashland and travel north, stopping at Schmidt Family Vineyards for lunch. Afterward, we continue our journey home, reflecting on five days filled with outstanding performances, beautiful scenery, and shared experiences.

Schmidt Family Vineyards

Stop at Schmidt Family Vineyards for lunch before continuing the journey home.

Lunch at Schmidt Family Vineyards

Enjoy an included lunch at Schmidt Family Vineyards before continuing the journey home.

Loading Map…

Map

1. Allen Elizabethan Theatre

15 S Pioneer St, Ashland, OR 97520, USA

2. Angus Bowmer Theatre

15 S Pioneer St, Ashland, OR 97520, USA

3. Lithia Park

59 Winburn Way, Ashland, OR 97520, USA

4. Downtown Ashland

E Main St & N Pioneer St, Ashland, OR 97520, USA

5. Schmidt Family Vineyards

330 Kubli Rd, Grants Pass, OR 97527, USA