milly roberts
Wilderness Retreats
A retreat into presence
3-5 day, guided backpacking trips through New England Wilderness.
Join an intimate cohort of creatives, carrying just what we need to stay 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-milage 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 2-3 hr driving from Boston, making these a manageable a 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:
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guided morning meditations
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nature awareness practices, opening our eyes to the often unseen
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miles of singing and miles of silence
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2-4 hour "artists date" solo experience
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non-linear forest explorations
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evening fire circles
These journeys are for those who...
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Can’t seem to carve enough time outside in daily life — and feel the cost of that absence.
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Have never backpacked, but ready to carry the weight and leave the creature comforts behind.
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Have backpacked and didn’t thrive in high‑mileage, high‑pressure expeditions.
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Love backpacking, and want deeper community, ritual, and nature‑connection.
There is an application process, as trips are limited to 8-12 participants. We aim to enroll eclectic cohorts of people who will bring a range of of skills and perspectives to the group.
2026 Wilderness Retreats
Summer Calendar
Summer Solstice:
White Mountains, NH
3 - Day | 6/19 - 6/21
20 miles, 3.3K ft Elevation Gain
This 3-day adventure is designed for retreat-seekers who crave a small challenge. Day one, we will hike in 5 miles to Flat Mountain Pond, where we’ll set up camp beside the water. From our home base, we’ll slowly meander up another 5 miles to a ridge line through the blooming White Mountains, before returning back to our campsite for for spacious solitude and reflection. Evenings we will gather around the fire for song and story. Meeting Spot: Flat Mountain Pond Trailhead Arrival: Friday 11 - 12 PM Departure: Sunday 4 - 6PM Group Size: 8 Participants, 2 Guides
White Mountains, Carter Dome
5 - Day | 7/9-7/13
24 miles, 6K ft Elevation Gain
This 5-day Backpacking Trek takes on the grandeur of the White mountains. We will start at Basin Campground, and work our way along the Wild River allowing generous time for river dips and rock kisses. We summit Carter Dome, "slack pack style" free of the weight of our full packs, returning to the same campsite for 2 nights. This 5-day journey provides challenge and beauty, silent mornings and festive afternoons, full of practices that unleash our creative spirit. Co-led by Milly and Shekinah, who bring 14 years of deep friendship, and a season of co-instructing at the CT Wilderness School together. Meeting Spot: Basin Campground, NH Arrival: Thursday 4 - 8PM Departure: Monday 9 - 11 AM Group Size: 8 Participants, 2 Guides
Singing the Berkshires
3 - Day | 8/7 - 8/9
9 mi. 3.3 K ft summit
Calling upon the Singing Circle Community - this 3-day backpacking retreat is for you. Co-led by song sisters Milly and Nicole, we’ll 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: 12 Participants, 2 Guides
A Sample Day
6:00 am — Rise & Stretch
6:30 am — Personal Practice
7:00 am — Breakfast & Plan for the Day
8:30 am — Silent Morning Miles
10:30 am— Session One (Guided Meditation & Sit Spot)
12:00 pm— Lunch & Rest
1:30 pm — Afternoon Miles
3:00 pm — Session Two (Movement Research: Dancing the Forest)
5:00 pm — Set Up Camp, Cook
6:30 pm — Dinner & Clean
7:30 pm — Fire Circle: Song & Reflection
9:00 pm — Tent Time
Your commitment:
1. Bringing personal gear: 50+L backpack, sleeping bag, pad, appropriate layers & rain gear is the bulk of it. See full detailed packing list here
2. Arriving at the trailhead: There will be a ride-share system offered for participants to coordinate through, however, you are ultimately responsible for arriving at trailhead within the arrival window. All trips begin within a 1.5 - 3 hr radius of greater Boston.
3. Pre & post group call: These calls are critical to both logistics and emotional safety, as we prepare to head off on a backcountry adventure together.
4. Assuming risk & responsibility: When we backpack, we walk our way to beautiful places, where emergency response is a longer process. With safety as a priority, some trips may require physical exam from a doctor ensuring your fitness for a backcountry expedition.
5. Financial commitment: A deposit of $70 - 90 (trip dependent) will be required to secure your spot, and will cover expenses for food and consumables. Program tuition is offered on a generous sliding scale, $50 - $180 per day, and will be requested upon completion of program.
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:
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That our bodies are not separate from the earth.
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That there is a creative life force moving through each of us worthy of our time & attention.
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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"
Contact
Here to answer your questions or field any inspirations or location requests for the Fall 2026 calendar.