A Pilgrimage with Teresa of Avila and John of the Cross

June 11 – 21, 2025

Avila and Toledo, Spain

Join Pilgrimage Leaders Jackson Droney and Bryan Berghoef to delve deeper into the interior castle of your life, trusting that God is at work in each of us.

Well and good if all things change, O Lord God, provided I am rooted in You. – John of the Cross

Registration will open by August 15, 2024. If you have questions, please contact the registrar, Chris.

Free Info Sessions

Join pilgrimage leaders Jackson Droney and Bryan Berghoef on Zoom to discern about the rightness of this pilgrimage for you. Choose a date below to register in advance.

We are living in turbulent times – a time full of “sacred upheavals.”

Our world grieves a staggering death toll and other losses resulting from the Covid-19 pandemic. Racial injustice, police brutality, gun violence, and environmental deterioration all weigh heavily. Economic and social changes abound. Political life and institutional life seem stuck. We are left wondering: how can we go forward? Where do we go from here?

Perhaps the answer is “Go deeper.”

God remains active amid all the loss, grief, and stuck places – in our personal as well as our communal lives. Teresa of Avila and John of the Cross remind us that detachment and delving deeper are the ways of the contemplative. Their teachings on spiritual deepening and the dark night of the soul have stood as contemplative guideposts for nearly five centuries. They challenge us to let go of old assumptions and temptations, of what is comfortable and familiar. Their wisdom about following God suggests a way through the impasses of our times. And beautifully, it is not something we have to work harder to attain. They invite us to experience “infused contemplation” – that which is received, not manufactured.

We invite you to join us in the sacred city of Ávila, Spain to learn from Teresa as we walk the same city walls she knew, as well as the ramparts of the interior castle of our lives. And in historic Toledo, one of Spain’s World Heritage Cities, we will turn to John and consider the communal dark nights of the present, while surrounded by the deep history of that place. Reflecting on our inner and communal journeys, we will embrace a pilgrim’s spirit of discovery and be open to what is and who we are.

Look inside: what do you see? As you look outside, how are you noticing and experiencing a dark night in this present moment? What might you release? Spiritual practice helps us see that life and our journeys are not binary—either/or, good/bad. And so, as we journey through the communal dark night, may we hear Teresa and John’s invitation to embrace the nighttime, personally and communally, while trusting that the dawn awaits.

The practice of pilgrimage centers on the transformation that takes place inside of us, even as we walk on ancient paths. On this pilgrimage there will be space to discern individually and in small groups how the Holy is nudging you in this time. There will be time for shared learning, prayer, and silence. We pray the Holy will move through and with us, revealing deeper truths to us in this most precious time.

Let us walk the ramparts of our lives together as we are, as we really are, trusting that God is at work in each of us, and all of us, through every uncomfortable and difficult step. Pilgrims will participate in listening groups throughout the week to notice the Holy’s stirring, and Gerald May’s book Dark Night of the Soul will frame much of the teaching and reflection for this time together.



The pilgrimage leaders will hold three monthly orientation meetings (via Zoom) with the pilgrim community. These meetings will be held at 7:00 PM Eastern on March 16, April 13, and May 18, 2025. Attendance at these 90-minute orientation meetings is required as they will provide a space to check in, offer important logistical information, and support the spiritual development of our pilgrim community. There is also an Optional Travel Meeting for Registered Pilgrims on January 5, 2025.


Day One

Wednesday, June 11: Arrival in Avila

We gather at our lodging in Avila, Spain in the late afternoon, beginning with an opening circle of introductions and setting our intentions for the journey ahead.

Days Two through Five

Thursday, June 12 – Sunday, June 15: Avila

We spend four days in Avila exploring the interior castles of our lives and walking in the footsteps of St. Teresa. Time will be spent in seminars, listening circles, and opportunities to experience the Holy’s presence in some of Avila’s most well-known sites. Pilgrims will also have ample free time, and one of these days will be spent in silence to reflect on our personal deepening with the Holy.

Day Six

Monday, June 16: Travel to Toledo

Pilgrims will have a “free day” in Avila before traveling by bus to Toledo in the late afternoon.

Days Seven through Ten

Tuesday, June 17 – Friday, June 20: Toledo

We spend four full days in Toledo exploring St. John’s teaching on Dark Night of the Soul and what it may mean for our communal journey. This time will include seminars, listening circles, and opportunities to experience the Holy in some of this ancient city’s historic sites.

Day Eleven

Saturday, June 21: Departure

Pilgrims depart for home.

The pilgrimage provided ample space for me to do important inner work, on my own and with others in the community. I remember now who and whose I am. And as a result, I have re-entered the world with fresh eyes and a gentler heart. I have been challenged to embrace and prayerfully traverse the dark nights and impasses within my own life, the Church, and the nation.”

-Caitlan Gartland, past pilgrim



Link to bio


Link to bio


$3,200 per person, double occupancy
Single room: $400 additional and subject to availability

Included in the Pilgrimage Fee:

  • Nightly lodging
  • Breakfast each morning
  • Dinner (except one night)
  • Bus transportation from Avila to Toledo, and from Toledo to Madrid Barajas Airport on the morning of June 21 (for those who want it)
  • Tickets for entry to historical sites that are part of the programed itinerary

The price does not include:

  • Airfare to and from Spain; ground transportation to Avila
  • Lunch
  • Dinner one night
  • Tickets for entry to sites not part of the pilgrimage itinerary that pilgrims may wish to visit on their free time

Payment Schedule:

Due upon application: $500 non-refundable deposit
Due on February 15, 2025: First installment of $1350
Due on March 15, 2025: Second installment of $1350
Due on March 15, 2025: $400 single room supplement for pilgrims who will be staying in a single room

Cancellation policy:

If you must cancel your reservation, refunds will be made as follows: cancellations received on or before March 5, 2025: 100% of monies received minus $500 non-refundable deposit; cancellations received between March 6 and April 12, 2025 50% of monies received minus $500 non-refundable deposit; no refunds will be made for cancellations received after April 12, 2025. Shalem reserves the right to cancel the pilgrimage for any reason, in which case you will receive a full refund of all monies paid.


Registration will open by August 15, 2024. Contact the registrar, Chris, to be placed on the waiting list.


Christine (Chris) Jeffrey is the Registrar for the Walking the Ramparts Pilgrimage and can be contacted at chris@shalem.org.


Our mission is to nurture contemplative living and leadership.


In 2025, Shalem will be a dynamic and inclusive community, empowered by the Spirit, where seekers engage in transformation of themselves, their communities, and the world through spiritual growth, deep connection, and courageous action.