Retreat Programs

Explore our retreat offerings. And remember! You can also visit us for a “self-guided” retreat any time.

If you’d like more information, or to make a reservation please contact our Guesthouse Office. Don’t forget to leave us your name and contact details so we may get back to you.

If you want regular reminders of soon coming retreat programs, click the “e-mail newsletter” button in the right-hand column.

Summer Individually Directed Retreats

Tuesday, July 22 – Friday, July 25
:: Led by the Monastic Community

*short written assignment before the retreat begins
*limited registration

Some time with a director and a good deal of time with silence this Summer. This is a retreat in which prayer and silence will be practiced as an invitation for deeper union with God and in which each participant will work with a spiritual director chosen by the monastic community.

Cost: $310, deposit: $80

The Guest House is closed from Monday, July 28th through Wednesday, August 20th. We re-open on Thursday, August 21st.


Associates Retreat
“Benedictine Archetypes of the Christian Life: Child, Worker, Soldier, Athlete, Student”

Friday, August 29 – Sunday, August 31
:: Led by Br. Randy Greve, Director of Associates

The Prologue of the Rule of St Benedict presents the great themes of all that follows. In it he defines, using rich imagery, what it means to be a Christian called to monastic life. Using the Prologue as the primary source, Associates and those exploring becoming Associates are invited to reflect on what it means to be in relationship with God as a; child, worker, soldier, athlete, and student. Each image adds something essential to our understanding of a holistic, balanced Christian life. We will examine the biblical inspiration Benedict quotes for these metaphors and their meaning and expression in our lives, especially in relation to the Associate’s Rule of Life.
Cost: $190, deposit: $80

Young Adult Contemplative Retreat

Friday, September 12 – Sunday, September 14
:: Led by Corey Krupowicz and Br. James Michael Dowd

This retreat is an opportunity for young adults to experience Contemplative Prayer. The Contemplative young adult retreat will offer an introduction into different techniques of prayer that we can practice in order to deepen our relationship with the Divine. Through the practices of Silence, Centering Prayer, Lectio Divina and the Divine Hours we will learn how to bring the ancient practices of contemplative prayer into our lives in a deeper way as young adults in this modern age.

Corey Krupowicz has been a practitioner of silent prayer for the last 15 years. He appreciates the importance in cultivating a contemplative path. At 34 years old, Corey is a member of the Episcopal Church, and an Associate of Holy Cross Monastery in West Park, NY. Corey is active within the Contemplative Outreach Young Adult advisory group, and will be completing his presenters training within the coming year in order to help young adults gain access to Contemplative prayer.

Brother James is the Guest Master at Holy Cross Monastery and has been practicing Centering Prayer and lectio divina for more than thirty years.

Cost: $215, deposit: $80

Fall Library Retreat

Tuesday, September 23 – Friday, September 26
:: Led by Brother Bernard Delcourt

Join enthusiastic volunteers for a labor of love – and balance work, prayer and recreation – as we continue the rewarding tasks of caring for and cataloging over 20,000 volumes.

Cost: $200, deposit: $80

River and Mountain Pilgrimage

Tuesday, October 7 – Friday, October 10
:: Led by Br. James Rostron
Limit of 8 participants

Join Br. James for several hikes along the Hudson River and in the Catskill Mountains. We will approach these outings as pilgrimage, with discussion and prayer to frame each hike. Please bring appropriate clothings, footwear, and other gear (water bottles, sunglasses, daypack, etc) for hikes ranging in length from 2 to 8 miles, rain or shine. The longest hike will be a full day and will likely include steep, rocky sections of trail with an elevation gain of up to 1800 feet. You are invited to bring tools for personal expression, such as journals, sketch pads, or cameras.

Cost: $225, deposit: $80

Prayerful Stitches

Thursday, October 16 – Sunday, October 19
:: Led by Br. Bernard Delcourt

Join us for the New York Sheep and Wool Festival and a prayerful focus on being mindful and intentional in our yarn work. Bring your own stitching material and technique of choice (knitting, crocheting, needlepoint, etc).

Cost: $370, deposit: $80

Contemplative Days

Tuesday, October 21 – Friday, October 24
Praying alongside the Monastic Community

A completely silent time with the monks as we observe our Autumn “Contemplative Days.” During this period we are in complete silence, no programs or spiritual direction are offered and there is a reduced worship schedule (Matins, Eucharist and Vespers). This will be limited to 15 guests who would like to enter into deep silence with us.

Cost: $225, deposit: $80

Sweet Roman Hand – A Calligraphy Workshop

Friday, October 24 – Sunday, October 26
:: Led by Brother Roy Parker

Shakespeare’s phrase for Italic handwriting in his comedy “Twelfth Night” indicates that the English aristocracy of his day retained Italian writing masters to teach them the newly developed script of the Italian Renaissance. Is your inner aristocrat yearning for expression? This workshop in the fundamentals of the Italic Hand could be just the ticket. Intended both for beginners and those who wish a refresher, it will teach the letter forms of the entire alphabet, leaving participants with a repertoire.

cost: $295, deposit: $80

The Myth of Redemptive Violence

Tuesday, October 28 – Friday, October 31
:: Led by Br. James Michael Dowd and Captain Ronald Steed, USN (ret)

You are invited to explore with us the myth of redemptive violence, paritcularly through the lens of Walter Wink, and the spiritual practice of non-violence, particularly through the lens of Benedictine spirituality. Through shared presentations, dialogue, prayer and meditation we will deconstruct the roots of the myth of redemptive violence within ourselves, our national mythology, and our Scriptural tradition. This retreat will contain both theoretical and practical approaches to non-violence.

Brother James Michael is an experienced retreat leader and spiritual director as well as the Guest Master and Sub Prior of Holy Cross Monatery. He has worked for many years in the areas of social justice and non-violence.
Captain Ronald Steed, USN (ret) transitioned from the Navy’s Nuclear Submarine Force in 2007. His last assignment was as the Commodore of Submarine Squadron Two in Groton, Connecticut. At sea, he was assigned to four fast attack nuclear submarines including NARWHAL (SSN 671), PITTSBURGH (SSN 720), and SEAWOLF (SSN 21). He commanded USS JEFFERSON CITY (SSN 759). After command, he was an Instructor for the Submarine Command Course. Today he is a Principal at UpScope Consulting Group, LLC where he conducts research and development involving command decision-making, team dynamics, and human factors. Additionally, he serves as the Senior Warden of St. James Episcopal Church in New London, CT, as President of the Homeless Hospitality Center of New London, and as an Associate of The Order of the Holy Cross.
Now in discernment for the Deaconate in the Diocese of Connecticut, Ron has been studying the works of Walter Wink regarding the Myth of Redemptive Violence and the nature of the Domination System. He brings an interesting metanoia perspective on the nature of these systems in world today as one thoroughly immersed in them, particularly at the national security level.
Ron and his wife Roxanne live in Mystic, CT.

Cost: $250, deposit: $80

Brush with God

Tuesday, November 11 – Friday, November 14
:: Led by Rev. Peter Pearson

For over twenty five years, Peter Pearson has been teaching others to
paint icons using the classic techniques of Byzantine iconography. In
each workshop there is a focus on the four fold way of iconographers:
technique, history, theology, and prayer. Each student will complete
their own icon from start to finish in a peaceful environment that
fosters a deeper experience of praying in and through the brush
strokes. This year, we’ll do a simple icon during out time together.
No previous experience or training in art is necessary and all materials
will be furnished. All
that is required is a willingness to let go and to try something new.
Please join us for this exciting journey into Byzantine iconography!

Peter Pearson, osb, has been painting icons since he was 12 years old
and has taught hundreds of people to learn to paint them as well. The
author of two books on icon painting, he is also the rector of The
Church of the Good Shepherd in Scranton, PA and a vowed member of the
New Benedictine Community, an ecumenical monastic community. Each of
these aspects of his life nourishes his soul as well as the souls of those he serves.

Cost: $465, deposit: $80

Alexander Technique

Friday, November 14 – Friday, November 16
:: Led by Bill Connington

The Alexander Technique Retreat features three days of intensive yet relaxing study with Bill Connington, a renowned, certified Alexander teacher with more than 20 years experience. The Alexander Technique is a 100-year-old method aimed at improving the way the body is used. A few of the many benefits of the technique are learning how to reduce tension and stress, improve posture, and manage pain. Those who may benefit from the technique are people in pain, those with physical restrictions, those who want to improve their posture; performers, musicians, athletes, and those interested in the mind/body connection. The workshop will be full of hands-on work, dialogue, in-depth learning, and fun. All levels are welcome from beginners to those who have studied Alexander extensively. Why not take some special time for yourself in a special place – and find a healthy mind/body balance?

Fees are $375 for tuition, room and board. The fee for commuters is $270. For more information, please visit register or ask questions, please contact Julie Donato at 845-227-2706 or

Christianity in the 2nd Axial Age

Friday, November 21 – Sunday, November 23
:: Led by Rev. Matthew Wright

Many thinkers today believe we are entering a “2nd Axial Age” that is transforming the face of religion and spirituality. How does this impact Christian faith? Is the Church becoming obsolete? This retreat will explore these questions, and look at the ways that Christianity is coming of age as a vital wisdom path for the 21st century, with particular emphasis on contemplative practice and interspiritual dialogue. What is an “interspiritual” Christianity? How can we be true to our own tradition, while opening ourselves deeply to another? How can we engage Christianity as a path of practice and transformation, and not merely a belief system? Come and join in a weekend of contemplative practice and intellectual inquiry as we tackle these questions together.

Matthew Wright is an Episcopal priest. Grounded in the practices of contemplative Christianity, his spiritual journey has also taken him through study and initiation in the traditions of Vedanta and Islamic Sufism. At age 29, he is a leading young voice in the field of interspirituality, exploring emerging new forms of religious identity and belonging. He lives alongside the Community of the Holy Spirit in Brewster, NY, sharing in the life and work of Bluestone Farm.

Cost: $275, deposit: $50

Thanksgiving, the Monastery Way

with the Monastic Community
Tuesday, November 25 – Friday, November 28

Harvest Thanksgiving is a wonderful and ancient tradition that calls us into a thankful relationship with God and with all of God’s creation. As Americans, we join with our sisters and brothers without regard to faith tradition in giving thanks, and as Christians, it is vital to give thanks and praise to God at every opportunity. At the monastery, we blend Americana (yes, turkey, dressing and the works on Thanksgiving) with religious tradition. Join us for any or all of these days.

Cost: $250 for all three nights, deposit $80

Advent Silent Retreat w/ Yoga, Meditation and Chant

Friday, November 28 – Sunday, November, 30
:: Led by Carolyn Bluemle
Limited to 15 participants

Advent throws us into a paradox of waiting for God while knowing that God is always present. The Gospel asks us to keep AWAKE: to be skillful in opening ourselves to God as hidden from us and to God breaking through in astonishing ways.

Yoga, chant, meditation, and mindful eating are all ways to become more attuned to the present moment, to be awake. With yoga we will pray through the body and align our posture that we may be more integrated, upright, and open. Some previous experience with yoga or meditation is recommended but not required.

We will have an opportunity on Saturday afternoon to worship with the full expression of our bodies, as each is inspired and able, with Taizé Chant and with posture sequences to a sung prayer.

Please bring a symbol of your intention for the retreat. We will place these on a prayer table in the practice room.

Carolyn Bluemle has taught yoga since 1989 and is Iyengar certified. She has led numerous retreats at Holy Cross and workshops in the Sacred Circles program at the Washington National Cathedral. She holds a Masters in ancient Greek philosophy from UC Berkeley and has enjoyed many years as a dancer. Through the healing practices of yoga, meditation, and Taizé chant she has renewed her Christian faith. Her teaching, precise and enthusiastic, with humor and compassion, reflects her deep experience of yoga as prayer.

Cost: $240, deposit: $80

Advent Contemplative Days

Tuesday, December 2 – Friday, December 5
Praying along-side the monastic community

A completely silent time with the monks as we observe our Advent “Contemplative Days.” During this period we are in complete silence, no programs or spiritual direction are offered and there is a reduced worship schedule (Matins, Eucharist and Vespers). This will be limited to 15 guests who would like to enter into deep silence with us.

Cost: $225, deposit: $80

Holy Cross Advent Retreat

“Re-Imagining Advent”
Friday, December 5 – Sunday, December 7
TBD – Save the date for this always wonderful Advent retreat!

Advent Individually Directed Retreats

Tuesday, December 9 – Friday, December 12
:: Led by the Monastic Community

*short written assignment before the retreat begins
*limited registration

Some time with a director and a good deal of time with silence this Advent. This is a retreat in which prayer and silence will be practiced as an invitation for deeper union with God and in which each participant will work with a spiritual director chosen by the monastic community.

Cost: $310, deposit: $80

Christmas, the Monastery Way

Tuesday, December 23 – Thursday, January 1 (closed Friday, December 26)
with the Monastic Community

Christmas at the monastery is filled with solemnity and celebration as we observe the closing days of Advent and then the great feast of Christmas, followed by the beauty and joy of Christmas-tide. We gather together as the shepherds did, to offer praise to God and to pray for peace on earth and in our hearts. Join us as we observe the ancienty cycle of monastic prayer from Advent into the Christmas season. Please note that the Guest House closes at Vespers on Christmas Day and remains closed throughout Friday, December 26. The Guest House re-opens at 2:00 on Saturday, December 27 and remains open through January 1.

Cost: $80 per weeknight/$95 weekend, deposit: $80

Welcoming the New Year: A Twelve Step Retreat

Tuesday, December 30, 2014 – Thursday, January 1, 2015
:: led by Sr. Shane Phelan, CMA

Each day is a chance to work our programs, but the turning of the calendar offers us a special chance to review and renew. Join us for the first day of the rest of your life, the first day of the year. We will spend time together, and also have time for quiet reflection. Some chances for individual sharing will also be available. A late-night gratitude meeting will be held on New Year’s Eve.

Members of all 12-Step groups are welcome. In a sacred space of anonymity and vulnerability, we can learn from one another and support those whose symptoms differ from our own, but who share the challenge of powerlessness over people, places, and things.

Sr. Shane Phelan has been involved in recovery work since 1985, across a variety of programs. She is an Episcopal priest and a member of the Companions of Mary the Apostle, a new women’s community located on the grounds of Holy Cross Monastery.
Cost: $240, deposit: $80

The Guest House closes at Vespers on Thursday, January 1, 2015 and re-open at 2:00 on Tuesday, January 13, 2015.