Wequassett Resort and Golf Club

The last full report of what was then called the Wequassett Inn was written by fellow travel journalist David Butwin. Since his visit, the original Inn has blossomed into a resort and tennis center has undergone a complete makeover, so thoughtfully undertaken that this little complex of four HydroGrid courts, the main one with lights, now stands out as one of the most beautifully designed tennis facilities anywhere. Terraced seating framed by stone walls overlooks the courts, which themselves have been framed in latticework fencing—which makes windscreens unnecessary—unlike any I’ve ever seen. Behind the terraces rise a pillared pro shop whose cupola sports a weathervane of crossed racquets. The shop itself has the decor and merchandise of an elegant boutique. There’s an outdoor barbecue more like a chef’s kitchen and an adults-only lap pool and Jacuzzi to one side, a children’s playground and kids’ club to the other. But though the tennis facilities are all brand new, the pro, Dave Messersmith, is the same man Butwin described years ago:

Wequassett has one of the best tennis bosses I have ever encountered. Dave Messersmith has been at Wequassett for 34 years. Steely hair, steel glasses, sterling game. He charges $80/$45 for a lesson, pretty reasonable in this day and age, but as he says, “My longtime customers have put in so many hours and so much money into this program I can’t charge them more.” [Management recently wanted him to raise his rates and he balked, keeping rates the same as they were when Butwin visited]. He is a delight to hit with, but more than just another pro who puts the ball on your racquet and gives you the illusion you are lifting your game, he explains, illustrates, imitates, while keeping up a steady stream of fascinating chatter and cannonading balls.

I hate when pros stop and call you to the net to over-wax on some salient subject; he works and plays at once, often aping the shot of a great player to make a point. And not just a contemporary great; he’ll go back to Okker and Tanner times. He can also make you look bad; the man has every shot in the book, and in playing points with my daughter, 16, he didn’t hesitate to hit ’em where they ain’t, again to prove a point. But he is quick to bark “Oh yeah” and “Too good” when you nail one.

Even as he massages your game, he surveys all that is around him, trading quips with the players on the next court, greeting the guest from Larchmont who has arrived early for his lesson. How he maintains this electric magnetic flow after so many years is just as remarkable as the shots that come off his racquet. Messersmith is there from 7 to 7 every day, ready to please, ready to play. Stay in a tennis villa and fall onto the courts.—David Butwin, Leonia, NJ.

David Butwin is a widely published travel journalist, who is as much at home on the tennis court (his daughter competed on the junior circuit) as he is on the canals of Venice.Tennis Programs. A substantial part of Messersmith’s time is spent on private lessons, though he does also offer daily clinics.

Court Complex: There are four clay courts, one with lights, all with underground watering.

Fees: $30/hour