Vermont Fall Retreat
The storybook Setting
Woodstock Inn & Resort
September 24–27, 2026
Woodstock is storybook New England at its best—walkable, charming, quietly elevated. Our home base is the iconic Woodstock Inn & Resort, right in the heart of the village so you can wander to shops, cozy coffee shops, galleries, and dinner without ever feeling rushed.
You’ll be staying in the center of it all—with 10 restaurants within walking distance, including two on property.
Come for fall colors ~ stay for the calm.
Golden-hour Vermont: fall air, cozy layers, and the prettiest light
Wander Time Built In: boutiques, galleries, coffee, and “sit with fall” moments
Indulgent Simplicity: slow breakfast → spa or stroll → lingering dinner
Connection Without Pressure: togetherness when you want it, quiet when you need it
wander plans
Not every destination supports the kind of retreat we’re creating—one that’s equal parts pause + polish. Woodstock does.
This Vermont retreat is designed for a small, women-only group—intimate by intention—easy to connect and effortless to enjoy. You’ll get the best of Travelers Well Wanders: thoughtful pacing, cozy-luxe details, culinary dining, and connection for both laughter and quiet.
Think: crisp air mornings, village wandering, unhurried meals, optional spa time, and golden-hour moments.
For the full flow of the weekend, scroll to below.
FALL COMFORTS
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Think beautifully paced, not over-planned. You’ll get storybook fall wandering, slow mornings, local dining, and signature moments—plus plenty of unscheduled space for spa time, reading, shopping, or simply doing nothing at all (the real goal).
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This is a small, women-only retreat with a warm, grounded vibe—where connection is natural, not forced. Come solo or bring your favorite person. Either way, you’ll be surrounded by women who are here for the same thing: a pause, a breath, a little beauty, and a weekend that feels cared for.
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Single occupancy isn’t just a detail—it’s the comfort that changes everything. This retreat is designed for women who want space to truly exhale: close the door, take a bath, journal, nap, stretch out, and move at your own pace—without roommate logistics or needing to be “on.”
You’ll have built-in togetherness when you want it and the quiet privacy to restore when you don’t. That balance is the luxury.
if you would like to share a room please note that on the request form -
You’ll love this if you’re craving:
A fall getaway that feels elevated, cozy, and easy
Me time without having to plan a thing
Connection as much—or as little—as you want
A retreat that feels restful and real, not performative
Perfect for women 35+, girlfriends, mother–daughter duos, and anyone who wants a gentle reset in a gorgeous Vermont backdrop.
Crisp air, Rest & repeat.
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(intentionally spacious — the goal is restored, not overbooked.)
As everyone arrives, we take time to settle in, get comfortable, and begin connecting with those around us. The journey starts here.Thursday, Sept 24 — Arrive + Exhale
Check-in at Woodstock Inn
Settle in + wander the village
Welcome toast + hosted dinner
Friday, Sept 25 — Wander + Indulge
Breakfast
Optional village stroll + shops/galleries/museums
Spa time / bikes / athletic club (your choice)
Evening at leisure (we’ll provide dining recommendations + reservations support)
Saturday, Sept 26 — Signature Retreat Day
Breakfast
Curated seasonal experience
Free afternoon: nap, bookshop, gardens, cocktail hour, spa add-on
Hosted closing dinner (the “wish we could stay longer” night)
Sunday, Sept 27 — Depart Rested
Breakfast + easy goodbyes
Optional morning movement or final village stroll
Depart
Final itinerary details + optional add-ons will be shared with confirmed guests.
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ALL THE DETAILS
Woodstock Inn & Resort |
September 24–27, 2026
This retreat is intentionally curated: an elevated stay in peak season, thoughtful pacing,
and the kind of details you’d never bother coordinating for yourself—handled.
Included:
3 nights at the Woodstock Inn & Resort (Sept 24–27, 2026)
Curated retreat pacing + hosted support throughout the weekend
Welcome gathering + toast
2 hosted group dinners - culinary dinning, zero planning on your end
Daily breakfast, unhurried mornings are the point
A signature fall experience
Resort access & amenities during your stay (athletic center, bikes, spa, local activities)
Basic Gratuities
Travel/Medical Insurance (required)
NOT Included:
Flights
Meals Not Listed
Alcohol (unless specified)
Optional Add-On Activities + Souvenirs
Taxis/Transportation for personal leisure
and add-on activities.
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If you need to cancel your participation in this group trip for any reason, our standard group cancellation policy applies (view it HERE). Because group travel involves contracted rooms, guides, and services secured in advance, payments are typically non-refundable and cancellation fees may apply, depending on timing.
Travel insurance is mandatory for all travelers. Coverage must include trip cancellation/interruption and emergency medical (and we strongly recommend medical evacuation). We’ll share the minimum coverage requirements and can help you select a policy that fits.
COVID-19–Related Exceptions
If the trip must be canceled due to COVID-19–related government restrictions, we will reschedule the trip or apply your funds to a future Travelers Well Wanders trip.
COVID-19–related reasons include:
Border closures that prohibit non-residents from entering or leaving the destination
Government-mandated quarantine upon arrival that materially impacts the trip experience
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FAQs
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Not here. If you’re 21+, you’re welcome. Most of our travelers are 40+, and that’s by design—women who know what they like, value comfort, and want travel that feels meaningful (not frantic). Mother–daughter duos are always a favorite, and multi-generational pairs are welcome when it fits the trip.
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Think: grown-woman energy.
Curious, grounded, kind. We’re here for great meals, beautiful spaces, meaningful conversation, and the freedom to be yourself—whether that’s early-to-bed, first-to-the-spa, or last-laugh at dinner -
Either is perfect. Many women come solo and leave with new friends—because we intentionally design these trips to feel warm, easy, and unforced. If you want to bring a friend, sister, or daughter, we love that too.
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You’ll fit right in. TWW itineraries are built with breathing room—a thoughtful rhythm of shared experiences and open time. Join the group when you’re feeling social, wander solo when you’re not, and know that both are completely normal here. No pressure to “perform” the trip.
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Safety is foundational. We work with vetted hotel partners and trusted local guides, monitor travel and weather advisories, and keep a clear, calm communication plan in place before and during the trip. You’ll also have direct access to your host while traveling, plus local support on the ground when needed. Travel should feel expansive—not stressful.
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Yes—travel insurance is mandatory for all TWW group trips. We’ll provide the minimum coverage requirements and help you choose a plan that fits (especially if you want strong cancellation/interruption and medical coverage).
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All booking terms and cancellation details can be found HERE. Because group travel requires contracted reservations secured in advance, cancellation terms can be more structured than individual travel—please review before booking.