Wequassett Resort and Golf Club
Chatham, Massachusetts
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By Roger Cox, Editor |
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The Inn sits on 22 wooded acres on the seaward side of Cape Cod on Pleasant Bay between Chatham and Orleans. Comfortable, expensive, and good for families, 
it may not, at first glance, seem to offer much to tennis players. It has only 4 courts (Har-Tru), but it also has one of the best tennis bosses I have ever encountered. Dave Messersmith 6has been at Wequassett for 30 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." 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. There are no arc lights, no night play, but 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 Features
Pro Shop: 508-432-5400
Other Recreation
Golf Courses. Wequassett adjoins the prestigious 18-hole Cape Cod National Golf Club, an otherwise private club open to Wequassett guests. Par 72, 6,954 yards.
And ... Sailboats, powerboats, and kayaks are available for rent at the Wequassett dock.
See Also
For comparison's sake, also take a look at:
- Fisher Island Club & Resort, Florida
- Four Seasons Costa Rica, Costa Rica
- Watercolor Inn & Resort, Florida
Rates and Reservations
Many of the rooms, suites, and cottages have water views and outside decks (the others look out on woods or gardens). Some add fireplaces.
Pleasant Bay
Chatham, MA 02633
Travel Essentials
Seasons. Year-round; however, the main tennis season runs from late spring into fall.
Travel Instructions. By Air: Wequassett is roughly 90 miles from Boston Logan International Airport (BOS) in Massachusetts and about 100 miles from T.F. Green Airport (PVD) in Warwick, RI. The regional Barnstable Airport in Hyannis is much closer.
General Tourist Information. For information about vacationing in Massachusetts, visit the Massachusetts Office of Travel & Tourism website or phone toll-free, 800- 227-MASS (US and Canada).
So far, I haven't received any written feedback on Wequassett Resort and Golf Club. If you've taken a tennis vacation there, I'd like to hear your reactions.