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5-Day All-Inclusive Workshop for Leadership in Business

March 15 - 19, 2026

Ashland, OR, United States

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Hosted By

Oregon Wellness Retreat

7 followers

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4 nights, 5 days

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7 person retreat

Highlights

  • Transform Your Leadership

  • Leadership Course for Executives, Owners, and Visionaries

  • Elevate Your Impact

  • Join a small group of like minded individuals

  • Instructor by EMyth Certified Business Coach, Tricia Amara

  • Luxury Accomodations

  • All-inclusive program and retreat

Details

March 15-19th 2026 Leadership Retreat This 5-day all-inclusive retreat is ideal for: - Business owners seeking growth, profitability, and operational clarity - Executives developing leadership skills, emotional intelligence, or strategic thinking - Visionaries ready to lead with greater authenticity and alignment - Guaranteed small group atmosphere for individual attention. - Fine dining and accommodations - Time for pampering, networking, and reflection - Check in between 3-6pm on the 16th. Checkout at 11am on the 20th Whether you're an entrepreneur ready to scale or a leader seeking clarity and confidence, OWR's Leadership Retreat offers a unique blend of strategic business coaching and soul-aligned leadership development. With 15+ years of coaching experience and a track record of building and selling three successful businesses, Tricia brings both practical acumen and visionary insight to the table. Business & Executive Coaching Tricia Amara, Business Coach With over 15 years of coaching experience and three successful businesses built and sold, Tricia Amara brings a powerful blend of strategic expertise and soulful leadership to business and executive coaching. As an EMyth Certified Business Coach, she has supported hundreds of entrepreneurs, leaders, and teams in improving profitability, streamlining operations, and unlocking the full potential of their business and leadership. Tricia specializes in strategic planning, business development, financial clarity, and team performance. Her executive coaching focuses on emotional intelligence, communication, and personal growth—developing the leader as much as the business. She believes entrepreneurship is a sacred path of service, and works with purpose-driven founders to help them lead with integrity, clarity, and soul. Each session is grounded, results-oriented, and tailored to your unique vision and goals.

Location

Ashland, OR, United States

Ashland, Oregon (97520), is a charming town in southern Oregon’s Rogue Valley, best known for its vibrant arts scene, natural beauty, and welcoming community. Nestled at the base of the Siskiyou and Cascade mountains, it’s home to the renowned Oregon Shakespeare Festival, which draws visitors from around the world. The town features tree-lined streets, eclectic shops, farm-to-table restaurants, and nearby vineyards, creating a lively yet relaxed atmosphere. Outdoor enthusiasts are drawn to its hiking trails, Lithia Park, and proximity to skiing and rivers, making Ashland a unique blend of cultural richness and scenic adventure.

Venue

Oregon Wellness Retreat

4.9 117 Reviews

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A 14-minute walk from the Oregon Shakespeare Festival, this relaxed bed-and-breakfast in an American Craftsman residence is 2 miles from the Pacific Highway and a mile from Lithia Park. The 6 homey rooms feature sitting areas, en suite or private bathrooms, and free Wi-Fi. Breakfast and parking are complimentary. There's a porch and a garden. Kids aged 10 and over are welcome with prior arrangement. Dogs are allowed for a fee.

A/C in Rooms

A/C in Rooms

Free Wifi

Free Wifi

Towels

Towels

Kitchen

Kitchen

Free Parking

Free Parking

Shower

Shower

TV

TV

Hairdryer

Hairdryer

Fireplace

Fireplace

Bathtub

Bathtub

Accommodation

Single Private Room

Private room for 1

$6,216 USD total

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The Bayberry Inn and Retreat is a charming pet-friendly Bed and Breakfast boutique inn near the heart of Ashland, Oregon. The Bayberry Inn and Retreat is a delightful historic house dating back to 1910. Meticulously restored and renovated, it now serves as a five-room, pet-friendly boutique hotel, retreat center, and bed and breakfast. The Inn's classic facade and old-world charm blend seamlessly with modern amenities, making it the perfect accommodation choice for your stay in Ashland.

Meals

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Meals provided

Breakfast · Brunch · Lunch · Dinner

Diets catered

Vegan · Vegetarian · Gluten-free · Dairy-free · Nut Allergy Friendly · Diabetic Friendly · Keto Friendly

Welcome Reception on the first day. We will partake in gourmet meals both on and off-site. Fine dining at award-winning restaurants. Catered and chef-prepared onsite meals. On or off-site dining will depend on each day's class schedules and locations. Dietary Allergies can be accommodated; we will discuss this ahead of time.

Schedule

Sample Day Itinerary (each days workshops are unique): 9:00 am — Group Breakfast at the Inn 10:00–11:30 am — Opening Circle & Intention Setting Purpose: Establish a safe, inspiring space; clarify individual intentions and group agreements. 11:30–11:45 am — Break 11:45–1:00 pm — Life Purpose & Core Values Mapping Purpose: Identify personal drivers and non-negotiables; create a foundation for authentic leadership. 1:00–2:00 pm — Catered in Lunch. Enjoy in room, the back garden, and the dining room 2:00–3:30 pm — Mission, Why & Impact Purpose: Articulate your leadership “why” and explore how it connects to broader organizational or societal impact. 3:30–3:45 pm — Break 3:45–5:00 pm — Strategic Visioning (Part 1) Purpose: Begin to craft a compelling long-term vision and priority areas for your role or organization. 5:00–5:15 pm — Reflection/Preview of Day 2 Purpose: Anchor insights and prepare for tomorrow. 6:00 pm- Full Hour Swedish Massage 7:30 pm - Dinner at one of the best restaurants in town. Enjoy walking around the adorable town

Testimonials

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"Josh and I decided on a whim to celebrate our 15th wedding anniversary by going on an art retreat. We found Oregon Wellness Retreat and before we could overthink it…pulled the trigger! Best. Decision. Ever! We had such an incredibly renewing, creative, expanding and delicious experience and made connections with some of the most incredible people we hope to know for the rest of our lives! I can not wait for the next retreat!! Thank you Bayberry Inn we’ll see you at the next one!" -Katherine Heigl "Can be found on her Instagram"

Katherine Heigl, American Actress, Producer,, United States

"A few weeks ago, I treated myself to a lovely art retreat vacation in Ashland, Oregon with Oregon Wellness Retreat at the Bayberry Inn. It was a wonderful week filled with hours of relaxing creativity, new friends, and amazing food. So fun!" -Astronaut Karen Nyberg (Can be found on her Facebook)

Karen Nyberg, American Astronaut, United States

"@katherineheigl and I had a blast on our #artretreat at the @oregon_wellness_retreat @bayberryinn438 last month - inspired, accomplished and well fed !! Katie laughs at this but now I’m into sculpting marble and I love it !! Look into this y’all- whether you’re aspiring or accomplished artists it’s so good for the soul!!" _Josh Kelley ( Can be found on his Instagram)

Josh Kelley, American Musician, United States

Exceeded my expectations!! I came for an artist retreat and got so much more! Jacqui and Billy were wonderful hostesses. Jacqui accommodated every single need from planning amazing art activities, delicious local restaurants, beautifully appointed rooms and even skin care items!! She was always gracious and kind. Billy is a cook extraordinaire! Every morning we were surprised with a delicious breakfast. I will live my life dreaming of his banana pancakes!! He was engaging and fun and attended to our every need. The town of Ashland city is charming and unique and has everything from outdoor concerts to shopping to lovely bookstores, amazing restaurants, gorgeous hiking, and worldwide acclaimed theater. If you want to relax , rejuvenate and reconnect- then this is your place. I made so many friends💕💕Forever in my heart. Beautiful Ashland City- Wonderful Bayberry Inn!!! - Freedom Sept 2023

Freedom, United States

"My best friend and I enjoyed a 3 day get away with Oregon Wellness Retreat, we had an amazing time. The hosts were extremely attentive and the Inn is beautiful! It was so relaxing to have everything planned out and paid for ahead of time so we could just enjoy the time we had. 10 out of 10 would recommend, I can't wait to go back!"

Kendall, united states

"We had such a wonderful time at the Bayberry Inn/Oregon Wellness Retreat! Jacqui and Billy are so friendly and attentive while you’re there, but it’s also the process of setting everything up that makes it amazing. Jacqui asked all of our preferences and setup our fabulous meals out (we can’t recommend Lovejoy’s Teahouse enough!!), theater experiences and any other activities or excursions that we wanted to do! The in-house made spa/bath products are also really lovely and made my skin so happy. Ashland and the inn itself are just gorgeous too! Do yourself a favor, go to Ashland, and stay at the Bayberry Inn!"

Allison and John, usa

“We Sent our Daughter for a getaway” Fabulous Inn With Caring Staff What a fantastic Inn!! Aside from the lovely furnishings and top notch food, Jacqui and Billy are spectacular hosts. Their kindness and attentiveness made our daughter’s trip to Oregon so fabulous, that we all stopped there on the way back to California. Truly a magical place with wonderful and caring staff. Could not recommend it highly enough!

Joel, USA

"My husband wanted to gift me with a pampered, joyful, and relaxing birthday celebration trip. Life has been hectic and challenging and he did not have a lot of time to plan every detail. He targeted Ashland and found Bayberry Inn's packages. Jacqui went above and beyond to connect with us early to get to know us to plan a wonderful celebration getaway down to the smallest detail. it was amazing. The restaurants, activities (e.g., play, Japanese bath house), time to wander, and touches (carefully placed roses, always available snacks and beverages, natural toiletry products made by Jacqui) were "made for us." And, we thoroughly enjoyed Jacqui and Billy's beautiful home, delicious breakfasts and welcoming charm. If you want a special celebration get away or just a break where you leave it to someone to wave their wand and create a wonderful memory, leave it to Jacqui and Billy."

Cynthia, USA

"For me life is all about great experiences, THAT is exactly what is offered with this retreat. Oregon Wellness Retreats, comes with a personalization, care, and uniqueness. Happy to have added a memorable experience to part of my journey."

Vanessa, USA

We couldn’t be happier with our decision to stay at Bayberry Inn. From early pre-trip communications and creating custom outings for our mini vacay to our trip to the airport on the way home…..all details were thoroughly planned and executed. Meals were delicious. Hosts, Billy and Jacqui are warm and welcoming and obviously enjoying being Innkeepers. Wonderful place to stay!!! And the beds was super comfortable.

Julie and Robert, USA

If you’re considering the Bayberry Inn, do not hesitate!!! We came all the way from Melbourne, Australia, and It was beyond our expectations. The innkeepers, Jacqui and Billy, are lovely, thoughtful, and generous hosts. We were lucky enough to meet their delightful families, who were visiting, and were never made to feel anything but part of the fun and warmth (but also felt free to do our own thing or keep to ourselves). Jacqui did an epic job planning an Oregon Wellness Retreat for my husband, parents, and I. From the food venues to the relaxation activities, we were continuously impressed. A very special place to come “home” to after a facilitated psilocybin session at Omnia. The town of Ashland is an absolute gem. We cannot wait to come back!

Marni, Australia

Jaquie and Bill have put together the wonderful OWR. I came solo to Oregon for a personal retreat. Somehow my needs were anticipated before I knew what I needed. The program that was put to together for me was beautiful. I explored Ashland but never felt lost or alone. Every person that was part of my experience was amazing. A lot of Gems in Ashland! The Bed and Breakfast is charming everything and more that you could want. The food! The company at breakfast was wonderful. I plan on coming back with my husband to see more of Ashland and the Rogue valley

Shelly, US

I am so grateful I got to meet Jacqui and Billy, during our staying in Ashland. Everything was so well taken care of and we felt the love since the moment we stepped in this beautiful Inn. Our room had a beautiful view on the garden and mountains around, it was very clean, cozy, and had everything we needed. Billy and Jacqui prepared a delicious breakfast every morning and I loved their mugs so much I had to take home 2!! You guys are amazing, thank you so much for taking care of us and making our stay one to remember. Come visit in Hawaii soon! Chiara and Nur

Chiara, USA

I chose this retreat for the combinations of pampering and wellness. From my 1st call Jacqui was inviting and welcoming. She explained the numerous options and put together a week of healing and self care. Once I arrived I was greeted at the airport where Jacqui and Billy's service was just beginning. Ashland is a beautiful town with lots of places to hike, shop and eat. While they made all the gourmet breakfasts the Bayberry Inn, my other meals were included at several hidden local gems. Jacqui and Billy checked in on me to make sure I had everything I need and even catered to my special request of Diet Coke. LOL I enjoyed spending time in the garden drawing and writing, definitely a place to get the creative juices flowing. I had the most amazing experience with the Sound Bath and the spa treatments were beyond my expectations. The Healing Waters soak was reinvigorating. I worked with Michelle on my Journey and the safety and growth I experienced with this team was everything I needed. I would recommend the Oregon Wellness Retreat to anyone seeking some downtime to rediscover themselves.

Kate, US

(If only I could give more stars!) Burned out from big-city life, I escaped L.A. for a week-long, all-inclusive self-care retreat at Oregon Wellness Retreat (OWR) in Ashland, OR—and I came home feeling completely renewed. OWR is run by the incredible husband-and-wife team, Jacqui & Billy, out of their charming Bayberry Inn B&B. From our very first email months ago, Jacqui listened to exactly what I wanted (deep self-care + great food) and built a custom itinerary that blew me away. Why I’m already plotting my return: 🌲 Immersive, personalized experiences • Private, guided hike in the Siskiyou Mountains with Billy—forest air, sweeping vistas, pure serenity. • Yoga Nidra, Japanese tea & bath-house soak, horseback riding through Applegate, acupuncture & cupping, multiple massages (the deep-tissue + sound-bath session with Sara Sai was one of the best I’ve ever had). Every activity was hand-picked and flawlessly scheduled. 🍽️ A surprise culinary hot-spot Forget small-town dining stereotypes—Ashland is a food lover’s dream. Some of my curated line-up included: • Wings & local brews at Growler Guys • Fresh pasta perfection at Osteria La Briccola • A mind-blowing 10-course tasting menu at James Beard finalist Chef Josh Dorcak’s MAS And each morning began with Billy’s gourmet breakfasts at the inn—delicious fuel for the day. 🏡 The Bayberry Inn home base Comfy suites, thoughtful touches, and hosts who treat you like family. You’re steps from downtown, so between sessions you can explore boutiques, grab coffee, or (dare you!) try a sip of Lithia’s famous mineral water fountain. ✨ The hosts make the magic Jacqui’s organization and warmth + Billy’s culinary and outdoor know-how = the dream team. They handled every detail; I just showed up and relaxed. Bottom line: Oregon Wellness Retreat is the perfect reset button—part luxury, part adventure, all heart. If you need rejuvenation, gourmet food, and genuine hospitality, book a retreat here. You’ll leave counting down the days until you can come back.

Nate, LA USA

Game-changer for my business “Tricia was absolutely a game-changer for my business. I came to her exhausted and overwhelmed feeling like I was responsible for every moving piece and part of my company. Through her guidance and wisdom I was able to create a self-managed company with clear systems and processes that is thriving! My leadership team does the heavy lifting and I’ve had more days off since working with her than I’ve had in the past decade of my career! I would highly recommend Tricia to anyone looking for a little less overwhelm and a lot more success!”

C.G. LA California, USA

Instrumental in my shift “I noodled on where we’ve been over the last two years. Can you believe it’s been that long?! And, wow!! What a journey I’ve had with you. It’s astounding to reflect on how much I’ve grown and how incredible I feel. You, my friend, have been at the core of my transformation — you have been instrumental in my shift to living this ridiculously joy-filled life, while diving into my life’s work with such courage, authenticity and trust that MyndJive is my purpose….my ultimate path. With all of the hugs and love, and deep gratitude for allllll of your unwavering love and support! ” — T F., Chicago, IL

TF Chicago, IL, USA

Lighting our path towards fulfilling our vision. “I have learned so much from you and am so grateful for your guidance in getting our studios on an upward spiral!! Thank you for seeing our potential, believing in us, and helping us clarify our vision and purpose. Thank you for providing us support and lighting our path towards fulfilling our vision. With Gratitude. ” — N D., Phoenix, AZ

ND Arizonia, US

My work with Tricia has been priceless not only for my business, but for me personally “My confidence as a small business owner has grown exponentially. Coming into this experience, I lacked direction, focus and knowledge on how to grow my business. My work with Tricia has been priceless not only for my business, but for me personally. She has changed my life in so many wonderful ways. I have and will continue to recommend her services to anyone in need of some direction.” — M L., Chicago, IL

ML Chicago, USA

Really felt like a had someone in my corner “I would never be where I am today without Tricia’s help. What we accomplished in 6 sessions is a testament to her expertise and many years of working with clients in similar situations. For the first time in my life, I really felt like a had someone in my corner, lovingly prodding me to move past my comfort zone. She became a calming presence in my life and I looked forward to our calls. When people tell me they need a coach, I give them Tricia’s number. ” — M H., Chicago, IL

MH Illinois, US

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Host

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Oregon Wellness Retreat

Ashland, OR 97520, USA

Oregon Wellness Retreat, located at the Bayberry Inn in Ashland, Oregon, has been recognized for eight years as one of the "100 Best Destinations in Oregon" and ranked in the "Top 3% of Hotels Worldwi...

1 language

English

Teaching for 4 months

Joined Insight Timer in Sep 2025

What's Included

Beautiful private guest room

All meals

Professional instructor and guide

Professional house host available 24 hrs

Snacks and drinks 24 hrs

Coffee and Tea bar 24 hrs

Optional mediation or yoga classes

Exclsuive materials/gifts are included

Retreat pics and videos will be shared with the group post retreat, with signed release

Personal pre and post retreat care

Some alcoholic drinks

Not Included

Flight costs

Travel Insurance

Visa fees

Additional activities not inlcuded in itineray

Spa treatments

FAQs

Guest requirements

  • Must be 18 or older or traveling with an adult

  • Please acknowledge classes will be taught in English

Cancellation policy

The remaining balance for the retreat is due 60 days prior to the start date. If this balance is paid earlier than these 60 days, you are eligible to cancel and receive a full refund of this remaining balance, provided you do so at least 60 days before the retreat begins.