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Photo of Wequassett Resort and Golf Club, Chatham, MA
©Roger Cox

Wequassett Resort and Golf Club

Chatham, Massachusetts

The Wequassett Resort and Golf Club sits on 27 acres of landscaped gardens, inlaid red-brick pathways, salt marshes, and woodlands on the seaward side of Cape Cod on Pleasant Bay between Chatham and Orleans. The 120-room property comprises some 22 historic buildings, among them the 1740 Warren Jensen Nickerson House, which was moved to this site and houses registration. Over the last several years, millions of dollars have been invested in serial upgrades, making what has always been a comfortable, if expensive, family-friendly property even more appealing. Tennis benefited greatly, getting a brand-new complex (see below), but so did the public spaces and accommodations (some of which are new). The main swimming pool snagged a prime location on a narrow spit of land with Pleasant Bay and the beach to one side, a picturesque sheltered Round Cove dotted with boats to the other. A boardwalk of Brazilian wood surrounds the pool, which has a raised area fitted with cabanas. Nearby terraces with firepits draw evening crowds—and frequent wedding parties. Shuttles leave from the pier below to drop guests an an ocean beach or take them on seal-watching tours.

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Tennis Features

Pro Shop: 508-432-5400

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 [now 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.
empty pixel 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.
empty pixelEven 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.


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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.

Children's Programs

That children's playground adjacent to the courts has a pirate ship, treasure chests, climbing ropes and water cannons outdoors, and an indoor center with games, televisions, and supervised programs for those ages 2 to 12. Tennis, swimming, and sailing lessons also available.


Their signature dining is Twenty-Eight Atlantic, an elegant room with 180-degree views of the bay and a menu long on seafood. Thoreau's, a tavern, focuses on steaks and seafood, while lighter fare is available at the Lybation, Outer Bar & Grille, and Pleasant Bay Terrace, all near the main pool.

See Also

For comparison's sake, also take a look at:

Rates and Reservations

Wequassett Resort and Golf Club

There is a variety of rooms and suites, ranging in size up to 3 bedrooms, with ocean or garden views. Many have terraces or patios; some have gas-log 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, check out Visit Massachusetts.