Wilderness Retreats

Aug 14 - 16 | Sept 18 - 20 | Oct 1 - 4

A retreat into presence

Multi-day, guided backpacking trips through New England Wilderness.

Join an intimate cohort of creatives, carrying just what we need to stay a little while in the wilderness, just far enough the birdsong becomes the loudest sound we hear and the mountain ridge opens onto... more mountains; we won't measure success in summits and suffering, but rather the rigor of our presence.

“I return to the wilderness to remember what I have forgotten, that the world can be wholesome and beautiful, that the harmony and integrity of ecosystems at peace is a mirror to what we have lost.”

— Terry Tempest Williams, The Hour of Land

beginner friendly

Led by experienced wilderness guides, and a low-mileage itinerary, so you can leave the stress of planning behind, and drop into retreat-mode.

nature immersion

The forest is the retreat center: We rise & set with the sun, drink spring water and fresh air, cook over a campfire, and reset to the pace of the forest.

among creatives

The forest is also the muse -- through tuning practices, non-linear explorations, ritual, and a good dose of clowning around, we feed the creative force in all of us.

in Boston's backyard

Trips are all within 1.5 - 3 hr driving from Boston, making these a manageable long weekend getaway. Carpooling available.

nature connection that fuels creative practice

There is a creative life force aching to move through us, and it's the same force that created the forest we dance with.

Our spacious itinerary will nourish this life force with time carved for:

guided morning meditations
nature awareness practices, opening our eyes to the often unseen
miles of singing and miles of silence
2-4 hour "artists date" solo experience
movement & dance explorations
evening fire circles

These journeys are for those who...

Can’t seem to carve enough time outside in daily life — and feel the cost of that absence.
Have never backpacked, but ready to carry the weight and leave the creature comforts behind.
Have backpacked and didn’t thrive in high‑mileage, high‑pressure expeditions.
Love backpacking, and want deeper community, ritual, and nature‑connection.

There is an application process, as trips are limited to the size of the campsite. We aim to enroll eclectic cohorts of people who will bring a range of skills and perspectives to the group.

Participant Application

Singing the Berkshires

3 - Day | 8/14 - 8/16

6-8 miles 1.5K elevation gain

Calling upon the Singing Circle Community - this 3-day backpacking retreat is for you. The same route as Solstice, but co-led by song sisters Milly and Nicole. Friday we hike a gentle 1.5 miles into a group campsite with picnic tables, fire rings, and a privy—an accessible entry into the wilderness. Once camp is set - we will adventure with a lighter load up to our summit, another 1.5 miles to an overlook with views of CT, NY and MA. We will bless the rolling hills with the songs they inspire, and bring the refreshed self back to our basecamp or an evening of fire, story and more song. Meeting Spot: Mt. Washington Head Quarters Departure: Friday at 12 PM Return: Sunday at 4 PM Group Size: 10-20 Participants, 2 Guides Cost: $279 - $534

Applications Closed

LGBTQ+ Land & Lake Retreat
Bigelow Hollow, CT

3 - Day | 9/18 - 9/20

1 - 4 mi/ day (mild elevation gain)

Join us for a weekend of woodland magic, as part of an inter-generational group of dreamers, dancers, mischief-makers, story-tellers, song-catchers, and curious creatures. This 3-day retreat is for LGBTQ+ folks who identify as women, genderqueer femmes, and non-binary people who were socialized as, or have past/present experience of being perceived as women. Our group – made up of adults of all ages – will hike, swim, cook, play, sing, stretch, create, and rest together, as we build a temporary community of curiosity and care. Our gentle itinerary involves 4 total miles of backpacking. Friday we will hike one flat mile with our backpacks to our lake-side basecamp where we will settle into a campsite equipped with a lean-to, tent-sites, fire ring, picnic table. Saturday hike 1 more mile to our lake-side campsite, followed by a day of pack-free hiking & lake-dipping. We’ll drop into guided group experiences, with healthy doses of serenity and earthling antics. The evening will close with a fire circle of cross-generation story telling and singing. Sunday we’ll gift ourselves a slow morning of lake-side meditations and an artist-date, before journeying 2 miles back to the trailhead. Meeting point: Bigelow State Park, CT Arrive: 12pm Friday September 18th Depart: 6pm Sunday September 20th Group size: 8 participants, 2 guides Sliding scale: $279-$534

Applications Open

Autumn White Mountains Retreat

4 - Day | 10/1 - 10/4

16 miles 4.2K elevation gain

This 4-day Backpacking Trek takes on the grandeur of the White Mountains in peak fall foliage. We will meet at Basin Campground, Thursday evening, for community building and preparation. Friday we hike with our full backpacks up to our basecamp, a shelter nestled between peaks. Saturday will be our “slack pack day” free of the weight of our packs, dipping in creek beds, singing & dancing along the Wild River Trail, before returning to the same campsite for a 2nd night. Sunday is a final challenge up a 3K ft summit and closing circle, followed by a slow meander back to Basin Campground for departure. This 4-day journey provides challenge and beauty, silent mornings and festive afternoons, full of practices that cultivate bravery and belonging in the natural world. Co-led by Milly and Naomi, of Orange Door Collaborative. Meeting Spot: Basin Campground, NH Arrival: Thurs. 4 - 8 PM Return: Sunday at 4 PM Group Size: 8 Participants, 2 Guides Cost: $372 - 672

Applications Open

We will bring all of the necessary group gear:

All food and cooking equipment, first air, water filtration, group shelter & more
Tents: You are welcome to bring a personal tent, otherwise we will provide 2-4 person tents for participants to share.

You are responsible for bringing personal gear:

1. 55+L backpack (rental available for $30)

2. sleeping bag & sleeping pad

3. appropriate layers & rain gear

See full detailed packing list.

Risk Management: The great outdoors presents natural hazards i.e. tick-borne illnesses, heat exhaustion, tripping & falling, among others. You will be responsible for following the instruction of your retreat guides on risk management practices for these hazards given the conditions of each trip.

In the case of an emergency, your guides are Wilderness First Responsers, trained to provide immediate care and determining if evacuation to the nearest emergency room is necessary.

Weather: Wilderness Retreats are rain or shine! The summer often provides us with 90+ degree days, intense thunder and rain storms. We will be prepared to retreat with the elements.

In the case of inclement weather that may risk our safety, i.e. an intense heat wave, persistent heavy rain and low temperatures, or tornado warnings, we will cancel the trip and provide a 75% refund of initial deposit, or 100% transfer to an upcoming trip.

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These trips are designed to be mild to moderate physical demand.

Carrying a backpack full of gear will be the most strenuous component. Choosing lightweight gear and simple meals will ensure we keep our pack weight down (and our spirits high). We aim to keep packs within the range of 25-32 lb, or no more than 20% of participants body weight.
While trips vary in milage and physical demand, these retreats all incorporate a "slack pack day" in which we set up camp, and hike the summit of our itinerary without our backpacks.
For participants who have never backpacked: It is advisable to go on a few training hikes acclimating to weight carry. Try out 2 - 4 miles, carrying about 15 - 25 lb. (1 L water = 2 lb)
You will be asked to complete a thorough Health History form, determining you fitness for a Wilderness Retreat. Participants with certain medical conditions may be required to get a doctors approval for participation.

A Sample Day

7:00 am — First Wake Up

7:30 am — Optional Movement & Meditation

8:30 am — Breakfast & Plan for the Day

9:30 am — Silent Morning Miles

10:30 am— Session One (Guided Meditation & Sit Spot)

12:00 pm— Lunch & Rest

2:00 pm — Afternoon Miles

3:00 pm — Session Two (Movement Research: Dancing the Forest)

4:30 pm — Set Up Camp, Rest, Cook

6:30 pm — Dinner & Clean

8:00 pm — Fire Circle: Song & Reflection

9:30 pm — Tent Time

why we retreat

Retreat comes from the Latin retrahere — to draw back, to withdraw. Together, as a community with the forest ecosystem, we draw back from the noise, speed, and extraction of the modern attention‑economy — not as escape, but as necessary hygiene.

We retreat to remember what modern life has taught us to forget:

That our bodies are not separate from the earth.
That there is a creative life force moving through each of us worthy of our time & attention.
That healing happens through action, ritual, and relationship — not insight alone.

As Mary Oliver reminds us, "we need not repent for miles and miles in the desert —

we only need to let the soft animal of our body love what it loves"

Participant Application

what participants are saying...

If you love not just "passing through" the outdoors, but really being in and with the natural world, connecting with our plant and animal kin, & reclaiming the wild and free parts of yourself - these retreats are for you! Milly and her co-guides do an excellent job both of taking care with all the logistics of an outdoor experience, and crafting an engaging and enriching experience for participants. The people who gathered for our trip were wonderful to be with, I left feeling a deep sense of appreciation and connection with the group as a whole.

I felt so well taken care of, considered and free to be myself on this trip away from the city! Milly’s blend of safe structure as well as space for spontaneity in the wilderness were perfect. These trips are for anyone who’s human and enjoys mildly roughing it to be immersed in beautiful nature & good company fir a few days :)

“this retreat was mind-blowing. Milly and her co-leads have such a deep reservoir of outdoor and community building experience, making it easy to do hard things and take care of each other.”

Interested,
but not ready?

sign up for the newsletter, for 1-2/month emails about upcoming trip annoucements and general inspirations from the field.

Contact

Here to answer your questions or field any inspirations or location requests for the Fall 2026 calendar.

millygraceroberts@gmail.com