Why I Ramble - JT's Tales From the Trail

Jill Thomas is a rambler, traveler, and storyteller with a big laugh who believes life takes her where she needs to go, no matter the roundabout path.

The pandemic changed me in many ways, but the most surprising was discovering rambling.

In the summer of 2020, my husband, whom I affectionately call Stormy, and I traveled to our home in Canada from our home in Pensacola, USA, as we had done every year for a decade. We found ourselves socially isolated on Salt Spring Island, Canada (the place where we raised our family).

Because of international travel restrictions, Jane Witherspoon, a long-time friend, and fellow Sole Sister Rambler Founder, also found herself stranded on the Salty Isle for months longer than she had planned.

Jane and I were close friends while we were raising our kids but had drifted apart. When we first met, Jane told me she didn't think we could be friends because she was an introvert and I was overwhelmingly outgoing. Luckily, this didn't turn out to be true. 

Our friendship faded when her marriage ended. After her divorce, she moved to Panama with her new love, our kids grew up, and we lost each other in the natural ebb and flow of a long-term friendship.

That summer, the pandemic brought Jane and I back together with time on our hands, and we decided to walk every road and trail on the island. We didn't complete this challenge, but we had fun trying and renewed our faded friendship.

Jane is fearless and unstoppable. She is an adventurous madwoman of a ramble buddy, which suits me. So when our summer of walking finally ended, we decided we would come back together and complete the El Camino in Spain the following spring. We never imagined that the pandemic would cancel our plans and stretch on for years.  

That fall, I returned to Florida and Jane to Panama, and we committed to walking the 420-mile El Camino de Santiago trail virtually. Stormy joined me for many of these walks during our Florida winter. The lockdowns were dragging on, and we were at our wit's end, craving distraction from endless episodes of the Great British Bake Off.

Our home in Florida was located on Pensacola Beach, a barrier island that is about 700 feet wide and 50 miles long, with the Gulf of Mexico on one side and the Intercoastal Waterway on the other. In the fall of 2021, a hurricane knocked out the main bridge to the island, so car access to the beach was a hassle. Mix in pandemic restrictions and cold weather, and we few beach locals felt like we had the sandbar all to ourselves.

Stormy and I used my virtual walking challenge as an excuse to walk daily. We found motivation by making it fun. Our rambles weren't exercise. Just a walk. We didn’t want to procrastinate for fear of huffing and puffing. 

We started with a mile, then two, and eventually three. Sometimes, we carried a cocktail in a travel mug. We meandered the empty residential streets and watched sunsets on the patios of closed outdoor bars.

We spent hours sitting on the empty beach after dark, something we had never done before, bundled in winter clothing, marveling at the patterns of the moon’s rays on the waves in the Gulf of Mexico. 

It was fun because it felt like play, so we did it enough to make it a habit. And suddenly, we found ourselves wanting to ramble more often. 

Jane and I finished the 420-mile Camino in three months. She bashed through Panamanian jungles while I wandered sandy, dark residential streets with Stormy and a drink. 

It was so much fun that we signed up for another challenge and invited my high school friends to join … Jill CM, Naomi, and Tara. Jill CM and Naomi were living in Toronto, Canada, while Tara was in Chicago, USA, preparing to move to Singapore. We are a tight-knit group and have remained close friends throughout the decades despite leading lives that scattered us around the globe. 

We created a Facebook Messenger chat to log our miles and post pictures of our walks while talking about the ups and downs of our daily lives. We referred to our walks as rambles, and these rambles became the highlight of our days.

Each of us, in our own way, had come to love long, meandering, destinationless outdoor rambles during the pandemic. We named our chat Sole Sister Ramblers. 

We continued to participate in virtual walking challenges and invited more women to join and our little group grew and grew.

Sole Sister Ramblers gave me daily contact with friends scattered far and wide. I also met new friends and forged deeper relationships with women I’ve known forever but not very well. We shared pictures of our daily rambles and cracked jokes about our mid-life challenges. It was fun and made the pandemic less lonely. 

This Sole Sister Ramblers chat enriched our friendships and lives in beautiful and surprising ways. So, in the Fall of 2021, we decided to share it with the world and launched a Facebook Group with a brightly colored winged shoe logo. This is how a ramble chat between five close friends became a global movement for women dedicated to connecting and empowering women in midlife and beyond.

So much happens in this beautiful space we’ve created with all of you. But rambling is the center of it all. Rambling means moving our bodies in ways that bring joy. It's meandering without purpose. Rambling makes being active a kind of meditation, an investigation, and a pleasure-filled ritual. 

Rambling strikes a pleasant balance between working and idling. It is a bodily exertion that produces interesting ideas, occasionally an epiphany, or just a way to decompress and free your mind. 

Rambling enables us to be in our bodies and the world without being made busier by either. It creates a feeling of a place that comes only from moving slowly through a landscape, at ease and without purpose. When we ramble, we discover new connections between the disparate elements in our most familiar places. 

Rambling falls into the beautiful category of free time. Prioritizing time to ramble defends this freedom, which is under constant assault. Rambling stands firmly in stark opposition to the anxiety of producing outcomes. When we ramble, time flows with unstructured ease.

Rambling is the opposite of arriving at a point of interest without regard to how you got there. For ramblers, the journey is more important than the destination. 

Walking is my favorite way to ramble. But I also enjoy cycling, paddling, and swimming. For me, few things are better than a long ramble with a friend and a meaningful conversation.

The women in this community ramble in many different ways. They walk, snowshoe, row, ski, hike, swim, cycle, sail, play tennis and pickleball, do yoga, and paddle canoes. They explore the world and their backyards. They go to farmer markets, concerts, and community events. Some hunt for urban murals, vintage treasures, and hidden #trailmagic.

While rambling, they connect with their grown-up children, partners, dear friends, and pets. Rambling is a blessing in our daily lives.

I can’t wait to hear your ramble stories. Happy Rambling!

READ MORE > JT's Tales From The Trail, Rambler Cafe Blog