Cliff Ross: More Than A “Halfway” Legacy

Cliff Ross was a wonderful, fascinating man.

A 1969 Staples graduate, his many professional talents included architecture and building.  He was also an excellent golfer, with a sweet swing.  He worked as a Longshore ranger for several years, beginning as a teenager.

It’s fitting then that one of the last homes he designed — before losing a long battle to pancreatic cancer this spring — was at the end of Owenoke.  From near the 10th hole at Longshore you can see into a window on its 2nd floor — all the way through to the Sound.

Even more fitting is that the fundraising drive for a new halfway house at Longshore is nearing its goal — thanks in large part to a $100,000 gift in memory of Cliff Ross.

A special event Thursday, September 22 — featuring a 1 p.m. golf scramble tournament, followed by a 6 p.m. cocktail party and auction at the Longshore tennis pavilion — may achieve the fundraising goal of $225,000.

But that would not have happened without Cliff Ross.

Cliff Ross

A passionate golfer (and senior club champion) who shot in the 70s even after his cancer diagnosis, he was a member of Westport’s Golf Advisory Committee.  He believed in the need for a new halfway house behind the 9th green — to replace the one destroyed by fire in 2003 — and was instrumental in the design and planning of its reconstruction.

The “9 1/2 Holer” group worked hard to make it happen.  They enlisted many local tradesmen to provide in-kind material and support to reduce costs.

Joey Romeo — the Longshore concessionaire — has promised to add a “Cliffburger” to the halfway house menu.

It — and the entire project — are fitting tributes to the memory of a kind, fair, honest, graceful and very giving man.

(The cost of the Golf Benefit on Sept. 22 is $200 — $150 per player for the 18-hole scramble, and $50 for the gala.  For further details, email, or call 203-858-4931.)

15 responses to “Cliff Ross: More Than A “Halfway” Legacy

  1. That’s a wonderful gift on behalf of Cliff. Is there a reason that the town isn’t paying for this project though? One reason a ton of people move to Westport (and our property values stay strong) are the terrific amenities (Longshore, the beach, our tennis courts around town) and I think this sets a bad precedent of pushing the costs of keeping those amenities top notch onto private groups rather than it being shared. It’s all of our responsibility to keep this town great. Many people without kids gladly pay taxes to make our schools top notch and keeping the beach and Longshore as top notch amenities seems like the responsibility of us all as well.

    • That’s not how the golf course works. Golfers, through greens fees and hand pass fees, pay all operating and capital gains costs for the management of the golf course. The irrigation system and the recent renovation were funded by direct increases in these fees. The town kicks in only for misc shared overhead costs or if the course runs a deficit.

      It doesn’t seem fair if you’re a retired golfer with no kids in the school system – and seeing the halfway house funding model as a precedent – not likely to change in favor of golfers anytime soon.

  2. Pope of the Slope

    Anonymous raises a very interesting subject. Anyone out there have the ability to explain how the “top notch amenities” draw in a substaintial revenue stream that seems to never go back into those “top notch amenities”?

  3. Cliff Ross was one of the most caring and courageous person I’ve ever met.
    He was a superb tennis player in high school before he found his calling on the golf course with his dear brother, Stu.
    Bob Uly

  4. The Dude Abides

    Cliff Ross was a great guy but a driving range would be more fitting as a monument than a half-way hamburger joint. Two roaming beverage carts with two employed students would do the job for about 20 grand instead of $300,000. Not to mention the slow play resulting from folks stopping for a burger. I am sure Cliff knew this as well.

    • I agree, but the project is gaining momentum. Maybe people are more interested in the burger than the golf.

      • The Dude Abides

        That may be true but where’s the beef? You put a golf course second and sure enough, American Golf or one such corporate entity will swoop down and gobble it up because Westport is losing big money on green fees. You put money in a course and they will come to play. You put your priorities and bucks in restaurants, you might as well go play Pine Creek.

  5. Pope of the Slope

    Cliff was a true gentleman. I know he realized that part of the golf adventure at any course, public, or private, was stopping at the halfway house to have the ability to refresh ones self before venturing to the back nine to hopefully, keep the good round going or start a run of birdies on the back nine. Our current structure allows for neither of those possibilities. As for pace of play, otherwise called slow play, it starts well before anyone reaches the halfway point and continues after one leaves the halfway point and that is where pace of play needs to be addressed.

    • If you sit down for a burger, it will take you 10 minutes or so to order/eat. That is a hole behind. It just took me 2 1/2 hours to play the front nine at Longshore due to some real diggers. So with lunch, that is close to 3 hours. Six hours to play 18 in an economy that is already stagnating the game of golf is really stupid. What you will find is that the folks will only play 9 holes and then have a leisurely lunch so total revenue on the course will be down and while we already allow out of towners to play now, Westport will ship in New Yorkers via the Peter Pan bus to play and we will have cigar smoking beer drinkers looking for their ball all the time. Nice. Dumb move. Hire two good lookers from Bogey’s with plenty of cleavage on beverage carts and serve the player while she/he plays. They make good tips, you get fresh food and no slow play. Duh?

  6. Maybe the Halfway House is just the beggining. Who says that’s the only improvement people are willing to support?

    • It is a question of priorities. Why the burger joint first? Cuz they got a big check? I may want a brothel there. Does that mean if I raise the money, I can get my wish? The driving range is a mess. Buy the beverage carts, put Cliff’s name on both of them and build a range where I can hit off grass or my driver.

  7. Pope of the Slope

    Wow, nice to see some great suggestions pouring in. They are all good. Once the halfway house gets done, we move on to a clubhouse, driving range, cart girls, beer, free golf for all seniors, kids on the course at 8:00 am whaaaa hoooo!………………. one step at a time.

    Oh and I don’t think Yale, Great River, Brooklawn…. anywhere, golfers stop and eat the burger at the halfway house. They order it, put it in the cart or walk with it, and eat it while continuing the round. Great course etiquette to sit for half an hour and eat. You think the ranger would let that happen…. NOT! Get a grip. Cut the long grass on the traps so one can find their ball. and you have just increased the speed of play by an hour.

    • Why don’t you just shorten the course to 12 holes and make the hole eight inches wide as did Nicklaus at Muirfield recently??? If you remember the old dump of a half-way house, people did stop and wait endlessly for their all-purpose-meat burger or a two day old dog. If they put a call-in order box on the 9th tee, it might work but otherwise, it will slow play down. And Cliff, bless his heart, liked to play fast.

  8. Thanks, Dan, for reminding us of Cliff Ross, who would surely be chuckling at this attention. I served on the Golf Advisory Committee with Cliff for years, and can attest that he was passionate about giving back to Longshore. He designed the new Halfway House, and it’s exactly what the course needs: A modest (750 sq. ft.) structure with nice new restrooms; a porch to take shelter from rain and lightning (and a place for parents to pick up kids after they’ve played nine holes) and, yes, a counter to grab a quick snack and beverage at the turn. Cliff was also very much aware that the town wasn’t likely to pay for the Halfway House, given its budget priorities, and that golfers would have to fund it. So be it. And hence, his simple, value-engineered design. Once built, it will be a wonderful legacy to a good man. Let me add this link to the website where you can get more info about the project: and make a contribution. Thanks again–

  9. Arthur B. Benjamin

    At a time of economic distress with one (1) out of every three (3) golf courses “under water” when it comes to financial stability, I am sure it is the
    time or right emphasis to build a $300,000 hot dog stand. Other suggestions mentioned here are far more practical and conducive to bringing players to Longshore.