Stand-Up Paddleboard (SUP) Spots on Cape Cod

Fifteen year old and trusty “Hercules” was built to haul stacks of SUPs.

Author’s Note: With summer temperatures setting records for heat, staying cool has become a priority. Avoiding the heat of the day requires some adjustment in one’s outdoor activity schedule, mainly getting outside early in the morning or around dusk. One outdoor activity that can keep you cool and has ballooned in popularity in recent years on and beyond the Cape, is stand-up paddleboarding (SUP). The over-sized, wide surf boards allow paddlers to cruise above the water’s surface or ride breaking waves while standing, kneeling or siting. It’s a great workout that you may not notice unless you are paddling against a headwind or have not figured out your balance (the latter point will definitely keep you cool with each and every splash).

There are two kinds of SUPs, hard core and inflatable. The hard core boards are better for deep, rough waters, like the ocean; inflatables are perfect for lazy, shallow rivers. Both work in fresh water ponds. When it comes to paddles, all are adjustable, but opt for the more sturdy, one-piece paddle. You’ll want the extra weight of a solid paddle compared to the lighter, easy to pack, two-piece paddle. Always make sure to have a leash wrapped around your foot and a personal flotation device on your waist or chest. Pro tip: keep the leash on the board, rather than in the water; as its drag will slow you down. Lastly, make sure you have the proper sized fins on the bottom of the board based on your activity. If you are paddling in a narrow river, you’ll want smaller fins made for quick turns that won’t scrape the bottom. If you are riding waves, you’ll want longer fins to help keep the board straight while getting pushed around by the waves. Now the more important question, where to SUP on Cape Cod? I got you covered. 

A sailboat floats with the gentle off-shore breeze.

Lower Cape

Long Pond (Brewster), Crowells Bog Road, is an enormous fresh water pond (for Cape standards) just off the Cape Cod Rail Trail with a dedicated swim area, small parking lot (parking permit required) and a wide boat landing. Be aware that motorized water craft (boats, wave runners, etc) are allowed on the pond. The motorized boats usual keep their distance so wave action is minimal. To avoid boat-created churn, keep to the edges of the pond or head to nearby Black Pond. Black Pond, next to the landing, is super small, but calm and surrounded by lots of greenery. Pro tip: If you do not have a Brewster parking permit, park in the dirt parking lot for the Cape Cod Rail Trail off Route 124. Parking is free and the walk to Long Pond is only six minutes. 

Hana came along for a short lap around White Pond, Chatham.

White Pond (Chatham), Wilfred Road, is a medium-sized, fresh water pond, tucked in between Route 28 and the Chatham Municipal Airport. It’s my favorite spot to paddle.The usually unoccupied pond is surrounded by cottages, moored sailboats, greenery, discarded sheds, tenders and benches. Every thirty minutes or so you’ll see a prop plane taking off in the distance. The off-shore breeze carries you south around the pond’s edge until a clearing appears to the right, with a second secluded pond area. It would appear to be a dead-end, but it is not. In the far left corner, a tiny opening takes you to, what I call, Hidden Cove. Hidden Cove is the fishing spot, as the entrance is concealed, shallow and narrow, keeping most kayakers, ‘SUPers’ and sailboats away. One day on that same water, I was actually inspired to write a poem. The small parking lot is never full and is right off the Cape Cod Rail Trail.

The party house at Goose Pond, Chatham.

Goose Pond (Chatham), Old Queen Anne Road, is tucked away in a conservation area, between Sam Ryder Road and the popular Corner Store. The uneven, narrow, dirt access road is a great way to get the heart pumping before arriving at the landing with a parking lot for barely four cars. The fresh water pond is small-to-medium-sized, with limited parking, but never busy. The red cottages tucked away in the left corner (east) are a throwback to the days when original property owners probably had the pond to themselves. Another house on the opposite side of the pond, fondly dubbed, the “party house,” as a tiki bar, hammock and beach toys are promptly displayed on the water’s edge. The owners have the right ideas as it’s (always) five o’clock somewhere.

The line of reeds acts as a line separating the beach and marsh areas.

Schoolhouse Pond (Chatham), Schoolhouse Pond Road, is one of two fresh water ponds in Chatham with lifeguards. The small pond is a popular beach for young families, and the parking lot fills quickly. Cars without a parking permit park around the bend off Sam Ryder Road across from Schoolhouse Pond Road. To the right of the swimming area, a shallow section leads to a secluded, back pond area “protected” by two lines of reeds, which almost look purposely planted. Thanks to the family-friendly environment, an ice cream truck plants itself in the parking lot.

Tenders await action on the sand.

Meeting House Pond Landing (Orleans), Barley Neck Road, is a salt water pond and active recreational harbor with access to Little Pleasant Bay. Not surprisingly, the departing and arriving boats create a bit of churn in the water, though the scenery of boats gently rolling with the tide, noise of an active harbor, and surrounding marshlands, make up for it. We did come across at least four seals on our journey, one of which kept pace with us most of the paddle. Thankfully, no “fins to the left, or fins to the right,” were spotted. The dirt parking lot provides ample, free parking.

Arey’s Pond Boat Yard (Orleans), Arey’s Lane, is not a GoT Targaryen reference, but a salt water pond and active “hurricane hole” (protected harbor) in Orleans. Owned by boat builder and designer Tony Davis, Arey’s Pond Boat Yard has restored over 300 sailboats, many of them wooden hulls, over 30 years and is the home to many boats awaiting their next adventure or waiting out the next storm. Being pressed for time, I only did a quick lap around (between) the moored (perhaps recently restored) boats, but discovered the snaking channel leads into Namequoit River into Little Pleasant Bay. Parking is limited.

Mid Cape

Hathaway’s Pond (Barnstable)Phinney’s Lane, is a medium-sized, fresh water pond nestled beneath the quiet shade of pitch pines and oak trees. Surrounded by hilly terrain and dense forest, the pond provides a restful atmosphere ideal for families and has a dedicated area to put-in a SUP or kayak. Unique to this pond, sixty feet below rests a purposely sunk 36-foot cabin cruiser (boat) for diving practice for marine emergency responders. Aside from its underwater oddities, the pond provides a beach with stunning views of the surrounding nature preserve and features a biking and hiking path under a natural canopy. Pro tip: It just so happens Cape Cod Beer is located a mere five minute walk from the pond. If you don’t have a Barnstable beach parking permit, you could park at the brewery and walk over. Just make sure to pick up a 4-pack or growler to ensure good karma and support the local economy for this childish parking hack. 

The steeple of St. Piux V Church is the landmark for Wings Cove.

Long Pond (Yarmouth), Indian Memorial Drive, is a large fresh water pond tucked away in a residential community in South Yarmouth. There is free parking at Wings Cove, near St. Pius X Church. The pond is surprisingly shallow along the edges, though there are multiple coves that feature interesting sights such as a white gazebo, red picnic tables, shabby docks, parks and of course a heck of a lot of lily pads. Off private docks you will find lots of fun inflatables. The steeple of the church in the distance will guide you back to Wings Cove.

The old pilings can be seen under the water in the foreground.

Little Sandy Pond (Yarmouth), Buck Island Road, is a small freshwater pond, part of the recreation area, complete with softball and soccer fields, basketball court, dog park, and walking trails. The pond is actually super small for a SUP, but, the tiny beach features crystal clear and warm water until a huge drop-off occurs about 20 feet from the shore. Along the left edge of the pond, I discovered a long collapsed and abandoned wooden dock, which was a bit mysterious as the land closest to the remaining pilings is dense woods. I also stumbled upon an odd looking, medium-sized turtle that looked more like a chicken in a shell. Mysteries at Little Sandy Pond.

Middle Pond (Barnstable) Hollidge Hill Lane, is a large fresh water pond perfect for fooling around on a SUP. Try new stances and push the limit of SUP balance. The water is clear, and no motorized powered boats make for smooth water. 

Outer Cape

On our way to Gull Pond after a day at Newcomb Hollow Beach, Wellfleet.

Gull Pond (Wellfleet), Valley Road, is a medium-sized, fresh water kettle pond that has an active SUP, kayak and sailboat scene. The small parking lot fills up by mid-morning since there is an active paddle club located at the water’s edge. Parking permits are required from 9-5. There is a dedicated swimming area near the landing, so young families looking for an alternative to the slammed Atlantic Ocean beaches have a refuge. I had a great time at Gull Pond watching my buddy fail at finding his balance for a good thirty minutes. 

Upper Cape

Boardwalk/Town Neck Beach, Boardwalk Road (Sandwich), is one of the most popular beaches in the area, with views of boats passing through the Cape Cod Canal. Paddle the lazy salt water river behind the barrier beach, or venture into Cape Cod Bay when the winds are low.

The Sandwich Boardwalk goes over the inlet on the way to Cape Cod Bay. Photo credit TripAdvisor.

Great Pond (East Falmouth/Teaticket), Maravista Avenue, is Falmouth’s largest salt water pond known for SUP fitness and yoga due to the calm water. It is a solid location for those new to SUP. 

Calm waters for paddlers and birds.

Great River, located in Mashpee near New Seabury, Will’s Work Road, offers ample parking and easy access to the calm waters of Jehu and Hamblin Ponds, or into Waquoit Bay with access to beaches that you won’t find in any tour guide. Translation, your very own private beach awaits!

Tall pine trees act as a landmark for John’s Pond, Mashpee. Photo credit: Secret Reel.

John’s Pond (Mashpee), Algonquin Avenue, is a large, fresh water pond and picture-perfect location to SUP or kayak with calm waters in a quiet neighborhood. The large, often unoccupied, beach, is unique in that it features two large pine trees at the water’s edge. Lifeguards are on duty and the town offers swimming lessons here.

Just beyond the woods lies Mashpee Pond. Naukabout Beer Company’s outdoor space is impressive.

Mashpee Pond (south basin) and adjoining Wakeby Pond (north basin), Fisherman’s Landing, is the largest fresh water pond on Cape Cod. While motorized water craft are allowed, which may create some wake, the location cannot be better because…the new Naukabout Brewery is located just off the south basin. After a long paddle, relax with a variety of craft drafts and a ton of outdoor games and music. Seriously, the brewery’s outdoor space is like Legoland for adults.

I’ve also heard good things about West Falmouth Harbor; Washburn Island, Waquoit; Mashpee’s Popponessett Spit; and Red Brook Harbor, Bourne. Where is your favorite spot to SUP on Cape Cod?

The Iconic Chatham Squire

The motto of the Chatham Squire, “Where friends get together,” says it all.

Author’s Note: There is no better ending to a summer weekend on Cape Cod than catching a Sunday evening Cape league baseball game at Veteran’s Field in Chatham. Recognized by fans and team volunteers as one of three top fields in the league (the other venues being Cotuit’s Lowell Park and Orleans Eldredge Park), there is always a good vibe under those bright lights. In the distance, behind the Chatham Fire Department, the setting sun signals the rush of the day has long passed, and a bounty of colors swirl in the sky amid a gentle salty, twilight breeze. Unique to Sundays, most day trippers and week-long vacationers have vacated the peninsula as they raced to get over the bridges hours earlier. And as fans settle into their seats after the singing of the national anthem, the “crack” of a first pitch fastball hitting the catcher’s mitt can be heard all the way down the first base line. Play ball!

While this scene was replayed on a recent Sunday evening, it was not until the end of the 7th inning when the real excitement began. Oddly, the excitement did not occur on the playing field. Chatham, like all Cape league teams, does a 50/50 and ‘handful-of-prizes’ raffle at the end of the 7th inning to raise money and keep fair-weather fans in their seats for the tense moments of those last innings. The raffle prizes range from harbor cruise tickets, specialty dessert vouchers, restaurant gift cards, and of course, half the cash collected. A few innings before the drawing, “bogey brother” Dan had to leave the game early and tossed his raffle tickets to us on the off-chance one would be a winner. Not only was one of his tickets called, but the prize was friend-favorite, a $50 gift card to the Chatham Squire (and two tickets on a Hyannis Harbor cruise). There could not be a more appropriate raffle prize, given all of our years of patronage. (Yeah, let’s go with patronage.) The best part of the ordeal was the delivery of the prize; kicked-off with a cryptic text message as soon as the envelope was received, followed by a stop at his house for delivery during a family nightcap on the porch. The astonished look of, “you’re joking,” was as glorious as expected. Later it dawned on me that the Chatham Squire donates this same gift card every home game (22 games per season) for as long as I can remember, which adds up to an $1,100 annual donation just to one organization. It’s also a good example of why a 51-year old restaurant is embedded in the fabric of Chatham’s community.

Indeed, a great 50-year run for Richard and George.

Much has been written about The Chatham Squire, as 2018 marked the legendary establishment’s 50th Anniversary. It also marked the last year of original ownership, as Richard Costello and George Payne, who started the restaurant and tavern in 1968, sold the business to Todd Hearle, a Connecticut businessman who grew up in Chatham. Fortunately, the intent is to change little, if anything, with the general manager and executive staff and many floor staff staying on. While it has only been two months since the change in ownership, I haven’t noticed any changes.

These license plates on the east wall of the tavern also says it all!

Now that the news covering the Squire has subsided, it’s as good a time as any for another long-time fan to chime in. Anyone who claims to know “about Cape Cod” surely has spent some time at this iconic Main Street destination. Whether elbowing your way to the tavern bar, listening to live music/trivia/karaoke from the table tops “upstairs,” enjoying a ‘quiet’ dinner in the dining room or getting rowdy in the back bar on a busy summer Saturday, The Squire has it all.

The collection of nearly 500 license plates from around the country along the tavern walls speaks to the come-as-you-are vibe. That diversity of experience is what makes the restaurant unique – plus the chowder is great, steamers do not disappoint, and I always seem to run into someone I know there. Admittedly, in the height of the summer season, it can be total chaos and you may want to avoid the lines and elbows. But during the day time, weekdays and especially shoulder seasons, its the local pub to have a good meal or drink at a good price. 

A hearty bowl of clam chowder and a cold draft beer are required starters, if you like that kind of thing.

In addition to the Chatham A’s, the Chatham Squire also supports many community events. The Squire’s logo can be found as a sponsor for First Night Chatham, both spring and fall Harbor Run/Walks (as after party host), on a float in the 4th of July Parade, and through many Chatham Chamber of Commerce events. 

Like many others, the Shaw and Healy crews are long time patrons of the Squire – especially in the winter months!

Having spent much of every summer in Chatham since 1983, I’ve put in a good chunk of time at the 487 Main Street property. As a kid, I recall a stern “mind your manners” moment while dining with my parents and grandparents in the main dining room. I remember staring at the ‘swinging door’ that endless hostesses, wait staff and patrons passed through, wondering what was back there.

As it turns out, “food” was behind the swinging door. The swinging door connected the dining room to the kitchen and to the tavern.

As a teenager, I recall catching a bite with my parents and brother in that once buzzing dining room, now nearly deserted, during a winter weekend. Snow was in the forecast, but had not started by the time we were seated. An hour or so later – and oblivious to the wet doormats and howling wind, we walked out into a full blown blizzard! The scene was magical. There were only parked cars on the road, and a handful of brave souls trying to get inside or to their car. the street lights and flood lights of each building illuminated the blanket of freshly fallen snow. As we slowly made our way to the car, wind gusts were swirling snowflakes in every direction on that chilly night.

As an adult, well, there were many nights started, continued, or finished at the Squire. A certain Squire loyalist (not me) also spent an evening of his bachelor party weekend at the Squire and may have been one of the most entertaining nights of my life. 

An old photo of The Chatham Squire from the late 1970s. Photo credit: The Chatham Squire.

Perhaps the most memorable experience at the Squire was the pending joy of standing in a 30-person deep line waiting to get into the tavern. It was the Saturday of Labor Day weekend…in 2002…I had just turned 21 years old. Admittedly – and this may come as no surprise – this was not the first time I’ve been in the Squire tavern. Cheers!

What is your most memorable experience at The Chatham Squire?