The Sisters Retreat
Sisters, Oregon
A joy-filled experience devoted to creative nourishment, soulful connection, and spirit-awakening inspiration.
We come more alive, more in tune with our hearts, and more inspired to live the lives that call to us.
I’m thrilled to offer this one-of-a-kind retreat in beautiful Sisters, Oregon, a charming mountain town that feels a bit like stepping into a Hallmark movie. Think art galleries, cozy cafés, and artful wandering.
Each day, we’ll gather in my private retreat home, lovingly converted into a creative sanctuary.
Imagine colorful farmhouse vibes, beautifully decorated rooms, a spacious studio, and plenty of indoor and outdoor spaces designed for gathering, creating, and resting.
Our days will be a lovely blend of creative play + exploration, guided wellness activities, and meaningful conversation.
We’ll also gather around for delicious meals, all lovingly prepared by our private chef, who is passionate about cooking nourishing food, farm to table.
I can hardly wait to share this experience with you!
“One of the most amazing experiences of my life.
– Cynthia Cary
What to Expect
I’ve designed this exclusive retreat to feel luxurious, deeply nourishing, and full of joy.
You can expect gorgeous details, and all sorts of thoughtful activities specifically designed to spark your creativity, nurture your being, and create long-lasting connections.
Throughout our time together, we’ll gather around and create in casual, informal ways, including a few easy painting projects.
We’ll also spend time walking around the lovely town of Sisters, OR where cute shops and art galleries are aplenty. Hello, inspiration!
We’ll attend the town’s beloved 4th Friday Art Walk together, sipping wine and admiring the local art.
You bring your creative spirit. I’ll bring ALL the supplies.
Wellness + Nourishment
I believe that we must find time to refill our wells, nourish our creative spirits, and take time to listen to our hearts. Taking time to exit our daily lives while being with kindred spirits is a beautiful act of self-care. Together, we’ll spend time quieting the noise and tuning into our hearts with guided ceremonies, writing exercises, and more.
We’ll also enjoy a couple of outings so we can take in the natural beauty of this area. There will be ample downtime for those of you who are seeking refuge.
You’ll leave feeling refreshed, nourished, and inspired to step back into your life with a renewed vibrancy.
Really good food!
We’ll be fed delicious, organic (when able) meals and snacks that will leave you swooning and wanting to take our chef home with you.
We’ll be well fed by our amazing chef who is deeply passionate about food and wellness. Wanna pick her brain about using food as medicine? She’d LOVE that!
Food never tasted so good.
Lots of time with me, Kelly Rae
I have always dreamed of hosting a one-of-a-kind retreat where I can float in and out of roles: Part art teacher, part girlfriend, part host enthusiast/geek, part mentor, part just another woman gathering with kindreds.
At this retreat I am here to host you, love you up, encourage you, guide you, and be a sister-friend. I’ll be sharing meals with you, lounging with you on the porches, as well as hosting and leading all the amazing activities I have planned for us.
I’m looking forward to spending this kind of rare, intimate, super quality time with you!!
Belonging + Connection
Every retreat I’ve hosted brings together the perfect constellation of women, a lovely blend of energies and personalities. Magic unfolds, connections are sparked, and lifelong friendships are born. Nothing delights me more than creating a loving, nurturing environment for deep connections to thrive.
It’s always a beautiful unfolding to witness. And I am always in awe.
Come meet your sisters is Sisters, Oregon!
“I have participated in Kelly Rae’s online courses, but nothing compares to the experience of being pulled into her open-heart way of being…
– Michelle Whitaker
Where we’ll gather 
Our retreat will take place in my private home in Sisters, Oregon, thoughtfully styled as a creative retreat space.
While overnight accommodations are not included, my warm, art-filled home will serve as our gathering place each day for meals, art-making, and connection. Consider it our cozy home base for the retreat.
The house blends modern comfort with charming farmhouse details, vintage finds, and colorful, artful touches throughout. It’s the kind of space where you immediately exhale and feel at home.
Inside, you’ll find a spacious studio created for gathering and art-making. There are inviting nooks to curl up with a journal, linger in conversation, or simply rest.
Outside, you’ll enjoy fresh mountain air, views of the mountains, outdoor seating, neighborhood deer, wandering town turkeys, and endless birdsong.
You’ll return each evening to your own nearby accommodations, carrying the day’s inspiration with you.
Hello, rejuvenation!
- Full retreat day gatherings in my private Sisters home
- Beautifully prepared meals + snacks, including 4 breakfasts, 3 lunches, 4 dinners
- All art supplies, including paints, brushes, papers, and more
- Generous goody bags, treats, and special surprises
- Heart-centered creative wellness exploration exercises throughout the retreat led by Kelly Rae
- Opening/closing ceremonies & dinners
- Fireside chats
- Many special, curated surprises
- Easy/close access to downtown Sisters, Oregon, which includes cute shops, a spa, and more
- Ample downtime to rest and restore
- Pre-retreat Zoom call
- Overnight accommodations are not included. A curated list of nearby lodging options will be provided upon registration.
- Airfare and transportation to/from Sisters, OR, though the Redmond airport is a 30 min drive to the retreat home
- Any alcohol outside of our Welcome + Closing dinners
“I have no words that can truly explain how my heart grew during the retreat.
Select Your Retreat:
AUGUST 13 – 17, 2026
You’ll enjoy all meals, art supplies, creative sessions, ceremonies, outings, and curated surprises, plus the ease of returning to your own space each evening.
Overnight accommodations are not included. A curated list of nearby lodging options will be provided upon registration.
Our time together begins at 4:00pm on Thursday, August 13 when we gather for the first time in my home, and wraps up with a final breakfast on Monday, Aug 17. I’ll send all the practical details ahead of time so your arrival feels seamless.
PRICE: $3300
MAY 21 – 25, 2026
You’ll enjoy all meals, art supplies, creative sessions, ceremonies, outings, and curated surprises, plus the ease of returning to your own space each evening.
Overnight accommodations are not included. A curated list of nearby lodging options will be provided upon registration.
Our time together begins at 4:00pm on Thursday, May 21, when we gather for the first time in my home, and wraps up with a final breakfast on Monday morning, May 25. I’ll send all the practical details ahead of time so your arrival feels seamless.
JUNE 25 – 29, 2026
You’ll enjoy all meals, art supplies, creative sessions, ceremonies, outings, and curated surprises, plus the ease of returning to your own space each evening.
Overnight accommodations are not included. A curated list of nearby lodging options will be provided upon registration.
Our time together begins at 4:00pm on Thursday, June 25 when we gather for the first time in my home, and wraps up with a final breakfast on Monday morning, June 29. I’ll send all the practical details ahead of time so your arrival feels seamless.
“I am so grateful that I got to spend the week with Kelly Rae doing her transformational workshop!
Frequently Asked Questions
Yay, I've signed up! When will you send a confirmation email?
Amazing! We’re gonna have such a meaningful time!
Please give me up to 24 hours to send your official confirmation email with all the details.
In the meantime, you can rest easy knowing that if your payment has gone through, your spot is officially reserved and secured.
I can’t wait to connect and make art with you!
How many people will be attending?
This retreat is intentionally small and intimate, with 8–10 women gathering together.
Keeping the group size limited allows for meaningful connection, personal attention, spacious art-making, and the kind of depth that only happens in smaller circles.
Are overnight accommodations included?
Overnight accommodations are not included in The Sisters Retreat.
We will gather each day in my private home in Sisters, Oregon for meals, art-making, connection, and all retreat programming. Each evening, you’ll return to your own nearby lodging to rest and recharge.
Sisters offers a variety of charming hotels, cozy Airbnbs, and walkable cottage stays just minutes from my home. Upon registration, you’ll receive a curated list of recommended accommodations to make planning simple and stress-free.
This format allows us to gather intimately during the day while giving you personal space in the evenings.
Where is Sisters and how do I get there?
Sisters, Oregon is a small mountain town in Central Oregon, a region people lovingly call “Oregon’s playground.” It’s full of fresh air, open skies, snowy peaks in the distance, and that cozy, artsy, small-town charm that makes you want to slow down and stay awhile.
The easiest way to get here is by flying into Redmond Municipal Airport (RDM), about 30 minutes from Sisters. From there, you can rent a car, rideshare, or connect with other attendees for a shared ride.
We’ll send detailed arrival info closer to the retreat so you feel totally supported every step of the way.
What's the weather like in Sisters, Oregon?
May in Sisters is typically mild and beautiful, with sunny days and cooler mornings and evenings. Since mountain weather can change quickly, we recommend packing layers (a light jacket, sweater, and cozy clothes).
Can you accommodate special diets?
Yes! We can accommodate many dietary needs (including gluten-free, dairy-free, vegetarian, and more). Before you arrive, you’ll have a chance to share your dietary restrictions and preferences so we can make sure you’re well taken care of.
What if I've never painted before?
You are so welcome here. Truly. You do not need any painting experience to come to this retreat. I’ll guide you step-by-step, and the creative time is designed to feel supportive, playful, and nourishing (not intimidating).
What supplies do I need to bring?
Nothing at all! All art supplies are provided and will be ready for you when you arrive.
The only thing I recommend bringing is an apron (totally optional, but awesome to have).
Will there be stairs/strenuous activity?
Yes, there will be some stairs. Our retreat home is two levels, and the art studio is on the second floor, so you’ll need to be comfortable going up and down stairs during the weekend.
We’ll also be doing some light walking around downtown Sisters, Oregon, and I’ll be taking you to a couple of my favorite local spots. Nothing strenuous or intense, just gentle exploring at an easy pace.
What's your cancellation policy?
A lot of love, planning, and behind-the-scenes work goes into preparing a retreat like this, and your spot is reserved just for you (including food, staffing, supplies, and accommodations). For that reason, we’re not able to offer refunds if you need to cancel.
If you’d like extra peace of mind, we highly recommend purchasing travel insurance to protect your investment in case something unexpected comes up.
If circumstances beyond our control arise, including acts of God, war, natural disasters, pandemics, or other unforeseen events, I reserve the right to retain retreat fees and reschedule the retreat or make necessary adjustments. Because significant planning is involved, rescheduling is often the most appropriate option.
I have more questions. How can I reach you?
Sure thing! You can always reach me at hello@kellyraeroberts.com.
“I was blessed in so many ways. Thank you for creating a safe space where we could bring our hearts for unpacking.
