A company outing doesn't have to mean reserving a restaurant, handing everyone a drink, taking a few group photos, and calling it a night.
Sometimes the best company outings are the ones where people actually get to spend time together outside their usual work environment, playing a round of golf, trying a new activity, sharing a meal, watching live entertainment, or simply having a conversation that isn't about the next deadline.
If you're planning a company outing in New York, The Villa Roma in the Catskills offers a great approach. Rather than building the entire experience around one restaurant or activity, you can bring meetings, recreation, dining, entertainment, and overnight accommodations together in one destination. And that opens up a lot more possibilities.
Why Go Beyond the Traditional Company Dinner?
A dinner can be great, but it's not always enough to bring a large or diverse team together.
Someone may be sitting at one end of a long table. Another person may leave early. And before you know it, the evening is over.
A well-planned company outing gives people something to experience together.
- A friendly golf competition
- A team activity
- A casual group lunch
- An evening of live entertainment
- A resort day away from the office
- A company celebration
- A multi-day corporate retreat
The goal isn't necessarily to make every minute a structured team-building exercise.
Sometimes the best connections happen naturally when colleagues are simply having fun together.
1. Turn Your Company Outing Into a Golf Day
The Villa Roma has a scenic championship golf course in the Catskills, giving companies an opportunity to combine a day outdoors with a social experience. The resort also offers dedicated golf getaway packages.
You could make golf the centerpiece of the outing or simply build it into a larger corporate experience.
A little friendly competition never hurts either.
Best for:
Corporate teams, client outings, leadership groups, sales teams, and companies looking for a more relaxed alternative to a formal event.
And yes , there will probably be at least one person who takes the score very seriously.
2. Plan a Company Outing Around Food
Food remains one of the easiest ways to bring people together. But instead of simply booking one restaurant, consider making dining part of a broader resort experience.
The Villa Roma offers multiple dining venues and bars, including Alba Nuova, Roman Garden, Café Villa, The 19th Hole, Bar Serata, Altura, and Splash Pool Bar.
That gives planners more flexibility when creating a group experience.
For example, a company might choose a more polished group dinner at Alba Nuova, while a casual gathering could fit better with the atmosphere of The 19th Hole.
The current Villa Roma website also highlights an Alba Nuova five-course dining experience, featuring Italian flavors and seasonal ingredients.
The takeaway?
Don't make dinner the entire outing; make dinner part of the outing. That small change can completely change the experience.
3. Take the Team Out of the Office , Literally
Sometimes your team doesn't need another activity, they simply need a change of scenery.
The Villa Roma is located in Callicoon, New York, in the Catskills, offering companies a setting away from the typical office environment. Its resort experience combines accommodations, dining, recreation, entertainment, golf, wellness, and other activities.
That makes it possible to plan a company outing that feels more like a getaway than another work obligation.
And that's especially useful for teams that spend most of their time behind screens.
4. Make It a Day Trip Instead of an Overnight Retreat
Not every company outing needs to become a two- or three-day event. If your team is looking for a day trip in New York, a resort destination can still provide plenty to do without requiring everyone to stay overnight.
You can structure the experience around:
Group activity → lunch → recreation → dinner or entertainment
The Villa Roma's broader resort offering includes activities and recreation, dining, golf, entertainment, and seasonal experiences.
This can be particularly appealing for businesses that want to organize something special without committing to a full corporate retreat.
5. Give Everyone Something to Do
Here's one of the biggest challenges with company outings:
Not everyone likes the same thing.
The golfer wants to play golf.
The social person wants to hang out.
Someone else wants to relax.
And there's always someone who says, "I'm good with whatever everyone else wants."
A resort setting can help solve that problem because the experience doesn't have to revolve around a single activity.
The Villa Roma highlights a variety of experiences, including golf, daily activities, entertainment, dining, wellness, swimming pools, and recreation.
That gives companies more flexibility when planning an outing for a mixed group.
6. Turn a Company Outing Into a Team-Building Experience
Team building doesn't always need ropes courses, trust falls, or awkward icebreaker games.
Sometimes it's simply about giving people an opportunity to interact differently.
A group outing could include:
- A friendly golf competition
- Group recreational activities
- A shared dining experience
- A casual social gathering
- Evening entertainment
- A combination of several activities
The Villa Roma's meeting and event spaces are also designed for everything from small workshops and team-building events to larger corporate conferences.
That means your outing can be as informal or structured as your company needs.
7. Combine Business With Fun
What if your "company outing" is actually part of a larger corporate retreat?
This is where The Villa Roma becomes particularly interesting for companies.
The resort currently lists 22,458 square feet of event space, 4,162 square feet of breakout rooms, eight large rooms, and 561 hotel rooms on its meetings and conventions page.
Its meeting venues range from smaller rooms for focused sessions to larger spaces such as The Club Forum, which is listed at 8,000 square feet and equipped with stage, lighting, and sound.
So instead of:
Meeting → everyone goes home
you can create:
Meeting → activity → dinner → entertainment → overnight stay
Why The Villa Roma Works for Company Outings
The Villa Roma combines:
- Meeting & Event Spaces: For conferences, workshops, presentations, and team gatherings.
- Golf: A scenic championship course for outings and golf-focused experiences.
- Dining: Multiple restaurants, cafés, bars, and dining experiences.
- Activities & Recreation: Options that allow different members of the team to enjoy the resort in their own way.
- Entertainment: Live music and other scheduled entertainment depending on the date.
- Overnight Accommodations: Hundreds of rooms that make it possible to extend the outing into a full retreat.
Planning a Company Outing at The Villa Roma?
The Villa Roma's events team accepts group proposal requests and can help determine the appropriate venue based on your event type, group size, setup requirements, and date.
