Back to All Events

Leadership Retreat – November 16-20, 2025


  • Bayberry Inn 438 North Main Street Ashland, OR 97520 United States (map)

5-Day Leadership Retreat: Align Your Purpose, Vision & Impact

Step away from the day-to-day and immerse yourself in a transformative experience designed to renew your clarity, focus, and leadership presence.
Over three days, you’ll explore your life purpose, mission, and values; develop a strategic vision for the future; and strengthen your leadership skills in an intimate, supportive setting.

Who This Retreat Is For

This retreat is designed for leaders, entrepreneurs, changemakers, and professionals who want to:

  • Reconnect with their life purpose and leadership “why”

  • Develop a clear strategic vision for their work or organization

  • Learn to create cultures of meaning and impact

  • Strengthen their leadership strengths and presence

  • Move from inspiration to action with a concrete plan

What You’ll Experience

Sunday Evening — Arrival
We’ll begin with a warm welcome reception to meet your facilitator and fellow participants, set intentions, and start building connections.

Day 1 — Mission & Impact

  • Opening Circle & Intention Setting

  • Life Purpose & Core Values Mapping

  • Mission, Why & Impact Workshop

  • Strategic Visioning (Part 1)

Day 2 — Leadership Strengths & Culture

  • Creating a Culture of Meaning

  • Leadership Strengths Workshop

  • Strategic Visioning (Part 2)

  • Afternoon free for rest, reflection, or exploration

Day 3 — Innovation & Action

  • Annual Planning Workshop

  • Innovation Lab (Creative problem-solving for real challenges)

  • Peer Coaching & Support Structures

  • Commitments & Accountability Planning

  • Closing Circle & Celebration Dinner

Each session is interactive and experiential, blending evidence-based tools with reflection, dialogue, and creative exercises.

What’s Included

Accommodations

  • 4 nights/5 days accommodations at Award-Winning Inn

    · 4 Breakfasts at the Inn

    · 24-hour coffee/tea/drinks/snacks

    Welcome Reception Dinner

    ·3 catered Lunches 

    · Dinner on the Plaza #1

    Dinner on the Plaza #2

    · Closing Group Dinner

    · 60-minute massage

    · “Healing Waters” Soak Evening

    Workshops

    • Pre-Retreat Virtual Session — Live Zoom call to set intentions and introduce      participants before arrival.

    • Senior-Level Facilitation — Three days of programming led by experienced      leadership coaches blending evidence-based tools with experiential learning.

    • Life Purpose & Core Values Mapping — Identify your drivers and build a      leadership foundation.

    • Mission, Why & Impact Workshop — Clarify your leadership “why” and link it to      organizational or community impact.

    • Leadership Strengths Workshop — Discover and leverage your unique strengths for greater influence.

    • Creating a Culture of Meaning — Learn to embed purpose and values into team culture and operations.

    • Strategic Visioning & Annual Planning — Craft and refine your vision and translate it into actionable goals.

    • Innovation Lab —Hands-on, creative problem-solving session to tackle real challenges and prototype new solutions.

    • Peer Coaching & Support Structures — Build accountability partnerships and      feedback skills.

    • Commitments & Accountability Planning — Turn insights into a concrete 90-day      action plan.

    • Assessments, Workbooks & Materials — Leadership assessments and worksheets      provided to support reflection and ongoing application.

    • Welcome Reception Dinner on Arrival Evening — Connect with fellow participants.

    • Closing Group Dinner on the Final Night — Celebrate progress and relationships before departure.

    • Post-retreat resources and peer connections to sustain momentum.

Accommodations

You will enjoy luxurious lodging and  accommodations at the Oregon Wellness Retreat at the Bayberry Inn,  transportation can be arranged to  and from the Medford airport (MFR) and to all included experiences. All  of your meals will be wonderful, whether they are prepared by Bayberry Inn's private chef on-site, catered by the best local eateries, or enjoyed at some of Ashland's finest restaurants. OWR's accommodations  have recently been awarded the title of BEST hotel in Ashland and are  among the top 3% worldwide.
The Bayberry Inn is a 5-block-walk from the World Famous Ashland Plaza and Lithia Park.

Pampering

We are sneaking in time for pamper and exploration as well. Included in your retreat is a 60-minute Swedish Massage, an evening at a Japanese Garden "Healing Waters", and tons of yummy restaurants. All fees, taxes, and gratuities are part of your package, so just enjoy. You've been working hard, you deserve it! 

Why Attend

By the end of this retreat, you’ll leave with:

  • A renewed sense of purpose and clarity about your leadership path

  • A well-defined strategic vision and actionable plan for the next 90 days

  • Tools to cultivate a meaningful culture within your team or organization

  • New perspectives, creative solutions, and supportive relationships

Reserve Your Spot

Spaces are intentionally limited to 6–8 participants

to ensure a highly personalized and intimate experience.