Media Backgrounder
A global community that connects and empowers women in midlife and beyond, one Ramble at a time. Everywhere is in Rambling distance with Sole Sisters!
Sole Sister Ramblers started the way the best stories do — with a chat between five longtime friends.
At the time, these five Canadian women in their late fifties—friends for decades— found themselves scattered around the world living in the USA, Singapore, Panama, and Canada. To stay close, they began doing virtual walking challenges together.
The friends created a chat group to log their miles, share photos from their walks, and talk about the ups and downs of daily life. They began calling their walks “Rambles” and named their chat group Sole Sister Ramblers.
Their Rambles and these associated chats quickly became the highlight of their days, enriching their friendships and lives in beautiful and surprising ways. So, in 2021, they decided to share Sole Sister Ramblers with the world.
And, that’s how a simple group message was the spark for a trailblazing global movement, connecting and empowering women in midlife and beyond.
As the community grew, it became clear that members weren’t just craving online connection — they wanted to meet in real life, too. In 2023, Sole Sister Ramblers launched its first Sole Circle, creating a way for women to connect locally for in-person Rambles.
Today, there are hundreds of Sole Circles worldwide, with more forming every week — and hundreds of locations on the waiting list.
Founder Naomi Weisman says, “It was a wonderful moment when it dawned on us that women on the other side of the world went for a walk and made some new friends because of us. And I was so excited when I was able to connect with other Ramblers when I visited New Zealand and Australia from my home in Canada!”
Today, Sole Circles have hosted thousands and thousands of Rambles around the world. Members gather for activities ranging from urban strolls and wilderness hikes to pickleball and golf, weekly lunch dates and book clubs, belly dancing and kayaking, cold-water swimming, yoga, and dragon boating. They also meet up to explore art galleries and museums, visit wineries, enjoy live music, and experience local community events together.
For the women who join them, Sole Circles quickly become so much more than a social calendar. They’re a lifeline — a place to build real friendships, feel supported through life’s transitions, and rediscover confidence, adventure, and joy. Again and again, members tell us that their Sole Circle helped them feel less alone, more connected, and happier— proving that a simple Ramble can be the beginning of something life-changing.
Founder Jill Morris says, “Rambling is what brings Sole Sisters together, but our Sole Circles are about so much more. Being part of our community provides our members with a profound sense of belonging. For them, Sole Circles are about connections, friendships, and memories created through shared experiences.”
Shortly after Sole Sister Ramblers launched, Founder, Jill Thomas’s sister was diagnosed with ALS at the age of 52 and passed away just 14 months later. Jill says, “Sole Sister Ramblers carried me through one of the most difficult times in my life. It made all of us realize just how essential women friends are as we face the challenges that can come into our lives in midlife and beyond — and that sharing the depth of our connections with other women is what Sole Sister Ramblers is truly all about.”
Eventually the Sole Sister Ramblers founders decided they also wanted a platform that helped women connect virtually around the world and so created a suite of Virtual Lifestyle and Fitness Challenges so members share their wisdom and experiences from wherever they lived. Sole Sister Challenges blend movement, mindset, and gentle accountability—bringing women together through daily goals, shared check-ins, and encouraging conversation. They’re designed to be supportive and achievable, meeting women exactly where they are and helping them build momentum toward a better life one small step at a time.
From walking and strength-building to gratitude journaling, self-care, reading, cooking and even mindful money management, our Challenges have become a powerful way for women to improve their daily lives in practical, sustainable ways.
Today, tens of thousands of women around the world participate in our Fitness and Lifestyle Challenges—finding connection, building confidence, and cheering each other on as they create healthier routines, deeper friendships, and more joy-filled lives.
Founder Jane Witherspoon says, “Sole Sister Ramblers has taught us the importance of friendship and community during a time when many women feel invisible and rudderless. Midlife and beyond is a time when women are able to focus on themselves after years of caring only for others. It is a time of empowerment but also of loss. Women need close friends and community to navigate all of this.”
The founders also wanted a platform to enable women to share their stories and so launched The Rambler Cafe Blog and our email newsletter to give women a place to share their experiences, insights, and hard-won wisdom—and to celebrate the real things that happen in midlife and beyond. From travel tales and personal reflections to honest moments of reinvention, resilience, caregiving, grief, and joy, these stories capture what it means to keep growing, exploring, and showing up for yourself in this season of our lives.
There’s something incredibly powerful about women telling the truth about their lives. When one woman shares her experience, it often becomes the encouragement another woman didn’t know she needed. These stories create belonging, spark bravery, and remind women that they’re not alone—offering connection, perspective, and inspiration in the most meaningful way.
Sole Sister Ramblers also partnered with Intrepid Travel, one of the world’s leading adventure travel companies, to offer unforgettable, small-group travel experiences designed specifically for women in midlife and beyond. Our travel adventures combine the ease of expert planning and local guides with the magic of traveling alongside other Sole Sisters—other like-minded women who value connection, curiosity, and meaningful adventure.
At Sole Sister Ramblers we believe unpredictably wonderful — and potentially world-changing things happen when women connect and empower each other in joy-filled communities. It’s an incredible feeling to know we’re playing a part in making that possible.
Founder Tara Romoff says, Watching that connection spark confidence, friendship, and real transformation has been the greatest gift of being part of building Sole Sister Ramblers.”
READ MORE > Our Story, Sole Sister Ramblers