Photos by Nathan Limbach
Cape Cod is renowned as a summer destination, but here’s a little secret: September and October might be even better. With the crowds gone, the beaches are tranquil, the water remains inviting (if still brisk), tee times are easier to secure, and most importantly, the oysters and beers are served at the perfect temperature.
On a recent Saturday morning at the end of October, I seized a flawless weather day and drove out to Wellfleet to play the Chequessett Club, a nine-hole Stiles and Van Kleek gem perched on the bluffs above Wellfleet Harbor, on the bay side of the peninsula. The club was about to close on November 1st for a two-year renovation in anticipation of its 100th anniversary in 2029. Having played Chequessett several times over the years, I wanted to capture some “before” photos, hoping to return for the “after” shots once renovations are complete.
But if I’m making the trip to Wellfleet, I’m not just playing nine holes and heading home, I’m taking full advantage of the off-season openness that makes the Cape so special.
My first stop was Nauset Lighthouse just before sunrise. Famous for its appearance on the Cape Cod Chips bag, Nauset’s iconic red and white stripes and easy access make it one of the most photographed lighthouses in Massachusetts. Whenever I’ve vacationed in Eastham or Wellfleet, seeing the sign for Nauset Lighthouse always signaled my arrival and helped my heart rate settle into vacation mode.
No trip to the Cape is complete without a stop at Hole in One Bakery on US-6. Opening at 6am, like any proper coffee shop should, their donuts are the main attraction. Powdered sugar, cinnamon, or Boston crème pie are all excellent choices. I always hope the name of the bakery will bring me luck on the golf course later, but so far, I’m still waiting for that magic to happen.
With coffee and donuts in hand, I head to Campground Beach just up the road to savor the sea air and the mile-wide sandbar at low tide, a sight hard to describe to anyone unfamiliar with Cape Cod Bay tides. I love watching dogs race along the wide, off-leash beach, a freedom only available during the off-season. The cool air, endless sandbars, and tidal pools offer a sense of liberation I can relate to, knowing I’m about to play a golf course that’s entirely open to me as the first tee time of the day.
Arriving on Chequessett Neck, I try to check in, but the pro shop is empty. A sign on the door gives me the go-ahead, I’m the only tee time before 10am and have already paid online, thanks to the modern “honor box.” The course embodies everything a nine-holer should: a fun layout, scrubby fairways with a mix of grass and dandelions, wild cranberries in the rough, greens that surprise and delight, and best of all, a brisk walk.
I soak it all in, sweeping dew off the greens and snapping photos. Before I know it, I’m at my favorite hole, the 5/14th, with two sets of tees playing either 109 or 170 yards. The hole asks for an uphill shot over scrubby grasses and wild cranberries to a turtle-backed green at the edge of the property. This hole could belong at a top-tier course anywhere in the world, from Scotland or Ireland to the Heathlands or Melbourne’s sunbelt. Discovering hidden gems like this is why I seek out nine-hole courses in small towns wherever I travel, you never know what you’ll find, and sometimes it’s truly remarkable.
Continuing on, the drainage issues Chequessett is addressing in its renovation become obvious, the next “fairway” is home to nearly a hundred migratory geese and ducks, and is completely underwater. I laugh as I tee up from the forward tees, turning the hole into a 241-yard downhill par-3, and laugh even harder when I hit a fantastic persimmon 5-wood to 15 feet right of the pin on a compact circular green.
After finishing my round, I chat with the pro in the shop, who shares details about the renovation and plans to expand operations. Wishing them luck, I set out for a couple more stops in Wellfleet.
Autumn means Oyster Season to me, and Wellfleet boasts some of the best oysters in New England. The local restaurant scene is outstanding, The Bookstore, Pearl, Boathouse, The Wicked Oyster, and Winslow’s are all excellent, but for lunch, I prefer the outdoor bar at Mac’s Shack. After a quick round of golf, a cold beer and a dozen oysters are just right. Sitting alone at the bar, no TV, just conversation with the bartender as they prep for the weekend lunch rush, enjoying oysters harvested that morning and a crisp local lager, that’s something worth writing home about.
My final stop is a short hike on the White Cedar Swamp Trail at Marconi Beach in the Cape Cod National Seashore. It’s one of my favorite light hikes; once you reach the elevated paths winding through Atlantic Cedar trees and their native swamp habitat, the silence is profound. In summer, the area is at least 15 degrees cooler, and on this day, fallen leaves blanketed the paths and floated atop the still waters, wrapping the entire scene in reds and oranges.
As I walked back to my car, Cape Cod was quiet and calm. The beaches were empty, the air was crisp, and the golf course was wide open, much different from the busy summer months. Fall brings simple pleasures: fresh oysters, open golf courses, and a peaceful walk on a leaf-covered trail. If you’re looking for a slower pace and fewer crowds, September and October are a great time to visit.
