Corporate Retreat in Hudson, NY

Some of the best work happens when you leave the office behind. At The Caboose, your Hudson Valley corporate retreat gives your team the perfect setting to breathe, think, and reconnect, under soaring beamed ceilings, flooded with natural light, with sweeping views of the Catskills and the Hudson River just beyond the door.

A thoughtfully designed meeting space with genuine historic charm and all the modern amenities your company retreat demands, just a short walk from the Hudson Amtrak and an easy escape from New York City.

From corporate meetings and breakout sessions to evening receptions and cocktail hours, our flexible 3,500 sq ft carbon-neutral barn adapts to your group size and agenda. It's the perfect blend of creativity, connection, and fun that every upstate New York retreat needs. Director of Culinary Hagan Whelchel and Bar Director Caitlin Frame lead the charge on food and drink, from farm-to-table menus to small-batch, boutique-label spirits that make the after-hours conversations the best part of any gathering.

And when the day is done, our sister property, The Wick Hotel, is a three-minute walk away: accommodations, dining, and entertainment all on one block, so your team never has to go far.

View our full deck to find the perfect fit for your next event.

STEP AWAY. THINK BIGGER. COME BACK BETTER

EVERY DETAIL, HANDLED.

Your team showed up to do good work. The least we can do is make sure everything else is taken care of. Every menu is designed around the rhythm of your day, energizing breakfasts to kick things off, working lunches that keep the momentum going, and seated dinners that turn a long day into a great one. All of it is prepared fresh, in-house, in our fully electric kitchen by a culinary team that takes the food as seriously as you take the agenda. You focus on the work. We'll handle the rest.

Just The Space

The most flexible entry point for teams that know what they need and want the freedom to make it their own. Just The Space is ideal for independent facilitators, creative off-sites, and small corporate teams looking for a scenic setting to plan, gather, and create without distraction. A clean, neutral backdrop that adapts easily to a diverse range of uses, whether that's a focused strategy session, a team-building activity, or a quiet planning day away from the office. This is your company retreat on your terms.
Start Time: Earliest Available — 7:00 AM
End Time: Latest Available — 9:00 PM
Space Access: Venue is unlocked at your contracted start time with a walkthrough and lockup at the end. Staff is available on standby for essential venue-related questions.
• Parking: 80 spaces
• Restrooms: 6 single-stall
• Accessibility: Fully ADA accessible
Plus, enjoy 6,000 sq. ft. of outdoor space designed as a native, biodiverse habitat with 14,500+ perennials, a perfect spot for team building activities and breaks in nature.
• Tables: Four 6' plastic folding tables
• Chairs: Sixteen chairs
• Waste + Recycling: Included
• Coat Closet: Self-service, Included
• WiFi: High-speed internet included
• Sound System: Hard-wired audio system (no iPad interface)
• Lighting Controls: Scene-based lighting presets included
• Water Station: Provided
• External Food: Allowed for non-catered items such as store-bought or homemade food (outside catering not permitted)

Big Ideas, Big Room

When your corporate retreat calls for the whole company in one room, Big Ideas Big Room delivers. This is the event space for groups that think and gather at scale, offering a luxury experience in a scenic setting that inspires creativity and drives results. Whether you're hosting a company-wide town hall or a multi-day corporate event, this is where big moments happen:
• Large Team Gatherings
Company-wide meetings, town halls, and presentations for up to 150 guests
• Half-Day & Full-Day Programming
Keynote sessions, panels, and multi-segment agendas with seamless A/V support
• Department Summits
Cross-team collaboration, strategy alignment, and annual planning in an inspiring setting
• Trainings & Continuing Education
Larger-scale learning, certification sessions, and workshops with room to grow
• Product Launches & Announcements
A polished, high-energy setting for big reveals, demos, and stakeholder updates
Start Time: Earliest Available — 7:00 AM
End Time: Latest Available — 10:00 PM
Space Access:
A dedicated on-site manager is present throughout your rental to support your team and ensure seamless operations from start to finish.
• Parking: 80 spaces
• Restrooms: 6 single-stall
• Accessibility: Fully ADA accessible
Plus, enjoy 6,000 sq. ft. of outdoor space designed as a native, biodiverse habitat with 14,500+ perennials.
• Tables: 8×36 Banquet Tables (22)
• Chairs: 200 Wooden Folding Chairs
• Waste + Recycling: Included
• Coat Closet: Included
Tableware includes glassware, utensils, and plateware. You choose the linen color for tablecloths and napkins
Included Amenities
• WiFi: High-speed internet
• Sound System: Hard-wired audio system with iPad interface
• Lighting Controls: Scene-based lighting presets
Optional Add-Ons
• Wireless microphone
• Chorded microphone + outdoor amp
• Rolling monitors
• Water Station: Provided
• External Food: Not allowed
F&B service is required with this rental.
In-House Catering & Beverage Services
• Seasonally driven menus
• Environmentally responsible culinary approach
• Fully electric, production-ready kitchen
• Extensive beverage packages
• Built-in bar with full barware selection

Huddle Up

Built for the work that actually moves teams forward. Huddle Up is the perfect setting for intimate gatherings and focused corporate events that call for a private, elevated atmosphere. Whether you're planning a leadership offsite or a half-day company retreat, this is the meeting space where new ideas take root and real connections happen:
• Team Offsites
Strategy sessions, planning days, and collaborative team resets that benefit from a change of scenery
• Half-Day & Full-Day Meetings
Structured agendas with seating for up to 50 and full A/V support
• Leadership & Board Meetings
A private, elevated setting for executive and board-level discussions
• Trainings & Workshops
Seminars, team trainings, and interactive learning sessions with room to move
• Client Presentations
A polished, professional environment for pitches, presentations, and partner meetings
• Small-Scale Celebrations
Internal wins, launches, and team appreciation moments done right
Start Time: Earliest Available — 7:00 AM
End Time: Latest Available — 10:00 PM
Space Access:
A dedicated on-site manager is present throughout your rental to support your team and ensure seamless operations from start to finish.
• Parking: 80 spaces
• Restrooms: 6 single-stall
• Accessibility: Fully ADA accessible
Plus, enjoy 6,000 sq. ft. of outdoor space designed as a native, biodiverse habitat with 14,500+ perennials.
• Tables: 8×36 Banquet Tables (22)
• Chairs: 200 Wooden Folding Chairs
• Waste + Recycling: Included
• Coat Closet: Included
We provide all tables, linens, seating, glassware, flatware, plating, and napkins — your only task is choosing the linen color.
Included Amenities
• WiFi: High-speed internet
• Sound System: Hard-wired audio system with iPad interface
• Lighting Controls: Scene-based lighting presets
Optional Add-Ons
• Wireless microphone
• Chorded microphone + outdoor amp
• Rolling monitors
• Water Station: Provided
• External Food: Not allowed
F&B service is required with this rental.
In-House Catering & Beverage Services
• Seasonally driven menus
• Environmentally responsible culinary approach
• Fully electric, production-ready kitchen
• Extensive beverage packages
• Built-in bar with full barware selection

The Annual Affair

For the corporate retreat that doubles as an unforgettable experience your team will talk about for years. The Annual Affair is built for companies ready to go all in on the agenda, atmosphere, and luxury experience. Set on a stunning property steps from the Hudson River, this is the perfect event space for high-impact gatherings that leave a lasting impression:
• Brand Galas & Corporate Celebrations
High-touch, fully produced corporate events for clients, partners, and internal teams that deserve the full treatment
• Fundraisers & Benefit Events
A polished, production-ready space for nonprofit and corporate philanthropy initiatives with real impact
• Large-Scale Corporate Functions
Company milestones, leadership gatherings, and organization-wide events that call for an unforgettable backdrop
• Premium Product Launches & Activations
A full-service environment for high-impact brand moments and experiential showcases that leave a lasting impression
Start Time: Earliest Available — 10:00 AM
End Time: Latest Available — 12:00 AM
Space Access:
A dedicated on-site manager is present throughout your rental to support your team and ensure seamless operations from start to finish.
• Parking: 80 spaces
• Restrooms: 6 single-stall
• Accessibility: Fully ADA accessible
Plus, enjoy 6,000 sq. ft. of outdoor space designed as a native, biodiverse habitat with 14,500+ perennials.
• Tables: 8×36 Banquet Tables (22)
• Chairs: 200 Wooden Folding Chairs
• Waste + Recycling: Included
• Coat Closet: Included
Tableware includes glassware, utensils, and plateware. You can choose the linen color for tablecloths and napkins.
Included Amenities
• WiFi: High-speed internet
• Sound System: Hard-wired audio system with iPad interface
• Lighting Controls: Scene-based lighting presets
Optional Add-Ons
• Wireless microphone
• Chorded microphone + outdoor amp
• Rolling monitors
• Water Station: Provided
• External Food: Not allowed
F&B service is required with this rental.
In-House Catering & Beverage Services
• Seasonally driven menus
• Environmentally responsible culinary approach
• Fully electric, production-ready kitchen
• Extensive beverage packages
• Built-in bar with full barware selection

THE CHANGE OF SCENERY THAT CHANGES EVERYTHING

A Venue with History

This wasn't always an event space. It was a centuries-old barn, and you can still feel it. The original white oak floors, the preserved rafters overhead, the little caboose railcar out front that gave this place its name. History lives here, right alongside 6,000 square feet of solar panels on the roof and a fully electric kitchen inside. That's The Caboose: the past and the future, coexisting beautifully, and the perfect place for your team to do the same.

And if a corporate retreat isn't quite what you had in mind, we host all kinds of professional gatherings here, too.

The Changemakers’ Rate

Big Impact. Smaller Bill. We know that every dollar saved on an event is a dollar that goes back into our community. To support the incredible work being done in the Hudson Valley and beyond, we offer exclusive rates for registered 501(c)(3) organizations:

The Venue: 50% Off Rental Fees. (Because we believe your budget should go to your cause, not just the room.)

The Fuel: 25% Off Food & Beverage. (Seasonally inspired catering from our Culinary Team to keep your team energized.)

Learn more

Why Host Your Corporate Retreat in Hudson at The Caboose?

Accessibility: Just a short walk from the Hudson Amtrak, an easy, car-free escape from New York City for your whole team.

The Wick: Our sister property is a three-minute walk away; accommodations sorted, no scrambling.

All On-Site: In-house A/V, culinary team, and bar, everything your retreat needs, all in one place.

Nature Meets Productivity: Soaring beamed ceilings, Catskill views, and a native perennial garden that doubles as the best breakout session room you've ever been in.