Goldie’s Golf Getaways: Wellfleet on Cape Cod’s Outer Cape





This week I’ve put together the quintessential Summer Golf Daycation.  We’re heading out to the fishing village of Wellfleet on Cape Cod’s Outer Cape for 9 holes of golf at the Chequessett Yacht and Country Club, a visit to The Beachcomber on Cahoon Hollow Beach and to top it off a double feature at the Wellfleet Drive-In Theater.  It’s hard to find a better golf daycation than this!

Welcome to Wellfleet

First Stop ~ The Chequessett Yacht and County Club, located just past the Wellfleet Harbor on Chequessett Neck Road in scenic Wellfleet.  This true Cape Cod treasure was founded in 1929.   Chequessett is a  semi-private Country Club offering a full array of Membership options that come with some great benefits.  For Summer visitors there’s also an extrememly popular Summer Kids Camp (4 days a week) offering tennis, sailing, golf, music and theater.

Chequessett's Kids Camp ~ Newly Renovated Boathouse

Chequessett offers sailing lessons for Juniors


Chequessett’s casual clubhouse usually has a refreshing breeze blowing in from Wellfleet Harbor.  I relaxed in one of the oversized wicker cape style chairs while admiring the trophies and award plaques that adorn the clubhouse walls from the 84 years of various Club Championships.  Pandora piping Frank Sinatra throughout the clubhouse brought me right back to 1950.  The spacious back deck has stunning views of the golf course and tennis courts and the aroma of hotdogs and burger from the deck’s grill are enough to tickle your taste buds – perfect for a quick bite and a beer or cocktail from the fully stocked bar before or after one of the many athletic activities available here.  Chequessett is a quite a popular destination for Cape Cod weddings and special events.

Chequessett's Board of Directors Meeting


For golfer’s Chequessett offers a Van Kleek and Stiles designed  9 hole Par 70 semi-links style golf course with 2 sets of tees for 18 hole play and relaxing views of Cape Cod Bay.   A spacious putting green greets you just off the driveway but there is no driving range.  For Tennis buffs,  an extrememly active Tennis Program features 3 Novapro and 2 asphalt Tennis courts and for salty sailors – there’s Sailing Club with a newly renovated boathouse right on Wellfleet Harbor.


Chequessett's Back Porch overlooks the spectacular greens!

Lessons for all Sports

Golf Professional PGA Pro Chris Hicks and Club Manager Barbara Boone, PGA are available for golf lessons and offer a fully stocked, full service Pro Shop.  During the season golf tournaments are held for Members and Guests alike.  Rental Clubs, golf carts and pull carts are also available.  There is a dress code.  A prime example of the Outer Cape’s laid back way is the ”Honor Box” which hangs outside the Pro Shop door for those locals and visitors who may swing by for a Quick 9 after hours!

Arthur B. Jerome Jr.  is the resident award winning Tennis Professional.  Tennis Lessons are available for all ages, Juniors thru Seniors.  Round Robin, Doubles, Mixed Doubles Leagues run though the season for those who enjoy a healthy dose of competition.

Chequassett’s Sailing program offers  group and private lessons and weekly Interclub Races.  Boat storage and moorings are also available for members which is a plus.

Chequessett's Pro Shop


After an enjoyable round of golf and visit at Chequessett it’s time to put on a pair of flip flops and re-apply my Golferskin spf 30 Sun Block cause it’s off to the The Wellfleet Beachcomber!

Looking down on Cahoon Hollow Beach from the Beachcomber's Parking Lot


A former Life Saving Service Station on Cape Cod’s National Seashore, the current owners bought the establishment in 1978 and have been rocking the dunes of Wellfleet ever since!  The Comber is located right on the Atlantic Ocean in the dunes on Cahoon Hollow Beach.  The casual ambiance is one of a kind and the Raw Bar, full menu and live music offer something for beach lovers, surfers and tourists alike.  You can’t beat the upbeat atmosphere and gracious staff and of course the beach – located a few steps from the parking lot.  If you’re a surfer the Outer Cape has some of the best surfing around and you can check the wind, water and wave conditions on Beachcomber’s website and see their live beachcam, stagecam and diningcam webcam feed too!  The Beachcomber has a great array of tee-shirts for sale for the fashionista’s in the crowd.


Lots of Beachcomber Tees For Sale

After a full day at Cahoon Hollow Beach it’s time to take in a double feature at The Wellfleet Drive-In Theater. Located just down the road from The Beachcomber on Route 6 on the Town Line between Eastham and Wellfleet, this is one of only 5 drive-ins left in Massachusetts and Cape Cod’s only Drive-In Theater.

Wellfleet Drive-In's Golf Cart



The Wellfleet Drive-In’s been creating Cape Cod Memories since 1957 on a 100’ x 44’ screen with FM stereo sound system equipted with Dolby Digital Sound and Barco Digital Projection.  For the traditional Old School drive-in experience, you can stream the sound through your radio or mono speakers are available in certain spots.  First Run Double Features are screened every nite rain or shine from Memorial Day to a little after Labor Day.   The Box office opens at 7:00pm and there’s a full snack bar and playground for the kids.  Be sure to bring your bug spray.

Be sure to check out my Wellfleet Golf Daycation Board on Pinterest!

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About Liza Churchill

2018 Marks WATD Sports Reporter Liza Churchill’s 10th New England golf season covering the local South Shore, Regional and National Golf Beat as a member of WATD’s Sports Team!