The 2027 Guide
The best executive retreats, corporate retreats and leadership retreats near New York City are a 70-minute to 2.5-hour drive away, in the Hudson Valley, the Catskills and the Bashakill area. Choose the format by the problem: whole company, top team or individual leader. Then set a budget, book a quiet venue and plan the 90 days after.
Five terms cover most of what people book. They differ by who attends and what the time is for: the whole company, the top team, one leader's growth, a coaching relationship or a specific piece of work. Use the table to name what you actually need before you call a venue or a planner.
| Format | Who it's for | Typical length | Typical group size |
|---|---|---|---|
| Executive retreat | The CEO and senior team, stepping back to think and set direction | 2 to 4 days | 4 to 12 |
| Corporate retreat | A department or the whole company, for connection, culture and shared strategy | 3 to 4 days (average 3.78) | 20 to several hundred |
| Leadership development retreat | Individual leaders building capacity through a structured method | 3 to 5 days, ideally with a later return | 6 to 16 in a cohort |
| Leadership coaching retreat | Founders and executives facing a specific decision or transition | 2 to 4 days | 1 to 10 |
| Leadership offsite | A leadership team doing defined work: strategy, planning, a hard decision | 1 to 3 days | 5 to 30 |
An executive offsite is a leadership offsite for the C-suite. For the full comparison, read Executive vs Corporate vs Leadership Retreat vs Offsite.
Expect roughly $1,500 to $5,000 per person per day for a facilitated executive retreat, about $3,000 to $4,000 per person on average for a corporate retreat, and $350 to $700 per person per night on site for a US offsite before travel. Root Astro's all-inclusive 2027 prices are $3,600, $7,600 and $9,200 per person.
| Format | For | Length | Price (all-inclusive) |
|---|---|---|---|
| Highland | An intact executive team of 6 to 10 | Tuesday to Friday | $9,200 per seat; team engagements typically from around $60,000 |
| The Bearing | Founders and operators, cohorts of 6 to 10 | 3.5 days, plus a virtual day-90 check-in | $7,600 per seat |
| Still Point | One leader, solo | Friday to Monday | $3,600 |
Our prices include lodging, chef-prepared meals, facilitation and every guided element. Travel is the only cost we do not carry. The full breakdown, and the questions that expose hidden costs anywhere you book, are in Executive Retreat Costs in 2027.
Taking it to your CFO? Start from our free one-page budget case template.
Choose by the problem you need solved. Whole-company connection calls for a corporate retreat. A senior team that agrees in the room but not in practice needs an executive retreat. A leader carrying decisions alone needs a leadership development retreat or a leadership coaching retreat. A deadline-bound decision needs a leadership offsite.
More on this in Leadership retreat vs team offsite.
Most retreat venues serving New York City sit 70 minutes to 2.5 hours away by car, across three landscapes: the Hudson Valley, the Catskills and the Bashakill area along the Shawangunk Ridge. Pick by category first: luxury resort, conference hotel, contemplative campus, planner-organized rental or purpose-built leadership campus.
The river corridor north of the city has the widest choice of corporate retreat venues, from historic resorts to boutique hotels with meeting space. It suits larger groups that need rooms and catering. See The 7 Best Corporate Retreat Venues in the Hudson Valley.
Further west, the Catskills offer mountain lodges and contemplative campuses, usually two hours or more from Manhattan. The distance buys quiet. See The 7 Best Leadership Retreats in Upstate New York and the Catskills.
The Bashakill, the largest freshwater wetland in southeastern New York (NYSDEC), lies in Sullivan County at the foot of the Shawangunk Ridge, about 90 minutes from Manhattan with no flight. Few large venues, which is the point: marsh, ridge and forest, little else asking for attention. Root Astro's campus is here.
A strong three-day executive retreat runs from an evening arrival to a morning departure, with devices handed in at the start. Day one tests the team through shared challenge, day two turns what surfaced into priorities on paper, and the final morning makes commitments in front of each other. Leave unscheduled hours every day.
A facilitator interviews every team member in confidence. The leader sees themes, never names, so day one starts with the real issues.
This is the shape of Highland. A larger corporate retreat can borrow the arrival, the device-free hours and the closing commitments.
The full hour-by-hour version, with a pre-work checklist and facilitator notes, is free: the 3-day executive retreat agenda.
Results last when the retreat ends with a written plan the participants built themselves, a few practices already on the calendar and a fixed date to measure again. Without those, the plan competes with a full inbox from the first Monday back. Treat day 90 as part of the retreat itself, not an optional extra.
At Root Astro, the Instrument reads six dimensions (Presence, Connection, Capability, Clarity, Resilience and Reverence) before the retreat, at the end and at day 90, and Highland and The Bearing both close with a handwritten 90-Day Bearing. Read What Happens in the 90 Days After a Leadership Retreat and How to Measure Whether a Leadership Retreat Actually Worked.
Device-free time gives leaders their full attention for the questions they came to answer. A 2017 University of Texas study found that a phone nearby drains working memory even when silent, and a 2012 study of wilderness hikers found that four days in nature without screens lifted creative problem-solving. Removing devices works better than asking people to ignore them.
At Root Astro, devices are surrendered on arrival and returned at the close, the leader included. Emergency contacts are held on file and first-aid certified staff are on the property throughout.
Root Astro, co-founded by Lee Arthur and Marsha Prospere, runs three device-free formats on a nature-based campus in the Hudson Valley, by the Bashakill wetlands and the Shawangunk Ridge, about 90 minutes from Manhattan: Highland for executive teams, The Bearing for founders and operators, and Still Point for one leader alone.
A Tuesday-to-Friday expedition for an intact executive team of 6 to 10, private to your company. Physical challenge, honest dialogue, a team-authored 90-Day Bearing and a virtual check-in at day 90. $9,200 per seat, all-inclusive; team engagements typically from around $60,000.Explore Highland.
A 3.5-day cohort for founders and operators, 6 to 10 people. Device surrender, a peer cohort, a handwritten 90-Day Bearing written on the final morning and a virtual cohort check-in at day 90. $7,600 per seat, all-inclusive.Explore The Bearing.
A Friday-to-Monday stay in a luxury safari tent. No group, no agenda, no devices. $3,600, all-inclusive. Explore Still Point.
The formats share one method: the Instrument, Truth, Health and Wealth goals, ancestral skills such as fire, archery and map-and-compass navigation, Creating Communitas and, for Highland and The Bearing, the 90-Day Bearing. Lee Arthur wrote Hard: Building Your Inner Citadel; Marsha Prospere runs an executive coaching practice.
The first season opens May 1, 2027. See every date on the 2027 calendar; Lee and Marsha personally review each application. Companies planning for several leaders can start at Enterprise, and funds and partners with a leader-development budget can find their route on Retreats. Questions first? Start a conversation.
An executive retreat is a few days away for a company's senior leaders, typically the CEO and C-suite, to think, talk honestly and set direction outside daily operations. Groups are small, usually four to twelve. Near New York City, most are held in the Hudson Valley or the Catskills.
They overlap but aim differently. An executive offsite is a working session, usually one to three days, built to produce a decision or plan. An executive leadership retreat gives the same team time to step back, rebuild trust and think before deciding. Many teams combine them; put reflection first.
A corporate retreat brings a broad group of employees together, often for three to four days, to strengthen connection and culture. An offsite takes one team out of the office, often for a day or two, to finish a specific piece of work. Judge a corporate retreat by how people connect, and an offsite by its output.
Match the venue to the group. For fifty or more people, you need rooms, meeting space and logistics, which favors resorts and conference hotels. For a senior team, privacy, quiet, access to nature and freedom from other guests matter more. Check Friday traffic on Route 17 and the Thruway.
A leadership development retreat is a structured, multi-day program that builds an individual leader's capacity through a clear method, facilitated sessions, assessment and a written plan. Leaders often attend as part of a small cohort from different companies. The best programs measure again at around day 90.
A leadership coaching retreat compresses coaching into a few days away: honest conversation with experienced facilitators, small-group dialogue and time to think without interruption. It suits founders and executives facing a specific decision or transition. At Root Astro, The Bearing combines peer cohort work with facilitation and a handwritten 90-Day Bearing, for $7,600 per seat.
A leadership offsite usually needs one to three days; Navan advises two to three for executive offsites. A leadership retreat needs longer, because attention takes time to settle: three to four days is a sound minimum. At Root Astro, Highland runs Tuesday to Friday, Still Point Friday to Monday, and The Bearing three and a half days.
Market estimates for facilitated executive retreats run $1,500 to $5,000 per participant per day, all-in (RetreatsAndVenues). Root Astro publishes its 2027 prices: Highland $9,200 per seat, The Bearing $7,600 per seat and Still Point $3,600, each including lodging, meals and facilitation. The drive from Manhattan is about 90 minutes.
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Explore Enterprise RetreatsDispatches from the field of human renewal. Irregular essays on leadership, nature, and the practice of becoming human again.
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