Paddling through the pandemic

Dana Gaines’ answer to the lockdown was a kayak.


It’s slushing out today. The wind is howling, and the snow and rain have made any thought of going outside a fool’s errand. Weather aside, it’s pretty much the same drill we’ve all been going through in lockdown for the better part of a year now.

We’re all desperate for a little release, which is why I’m excited to write about kayaker Dana Gaines of Edgartown, so we can live vicariously through how he chose to deal with the pandemic. Rather than staying home and bingeing on Netflix, Gaines elected to get out on the water and share his experience with the rest of us. He called his project Paddling Through the Pandemic.

Gaines is an illustrator, and owns Kayaks MV and represents Stellar Kayaks, based in Northfield. And had it not been for a canceled trip to the British Virgin Islands, his Paddling Through the Pandemic project would likely never have seen the light of day.

Normally, every spring, Gaines travels down to his rental cottage on Virgin Gorda to get some sun and to kick off the kayaking season. But this year, the pandemic threw Gaines a curveball. The British Virgin Islands had shut down its borders, so Gaines was forced to stay home.

Not one to sit idly by, even though it was the middle of March, Gaines was looking for an excuse to get out on the water, so he paddled across Katama Bay to a house he owns on Chappaquiddick. It was great to get out in the fresh air and get some exercise, but what really came across to Gaines was the silence. Sound usually carries across the water, but because construction had shut down, there were no sounds of heavy equipment, no other boats, and very little vehicle traffic to interrupt his solitude. It was just Gaines and the sounds of nature.

It had such a profound effect on him that he wanted to share it with his friends, and he knew just how to do that: He’d record his trip on an app he’d been working with called Relive. Relive was developed several years ago by cyclists who were interested in documenting a cycling event on the Canary Islands. The technique uses GPS mapping services to track the precise course of an event, and combines it with still and video photography and music. It gives the viewer “an animated, bird’s-eye view of the event,” Gaines said, “showing the viewer exactly where you are at any given time.”

Gaines had originally heard of the app from his friend, Dave Diriwachter, who was using it to document a road race on the Island. Gaines became obsessed with the idea, and thought it would be a good way to document his kayaking adventures.

The weather had been nasty in April, but April 6 turned out to be a beautiful day, and Gaines set out for Pocha Pond in Edgartown, posting his trip on Facebook using Relive. He immediately got a positive response. “I think it struck a chord,” Gaines said. “People were tired of being locked down, and they wanted to come along with me for the ride.” And this is when Gaines’ Paddling Through the Pandemic idea was hatched. His plan was to paddle around every bit of Martha’s Vineyard coastline, every bay, harbor, and pond that was publicly accessible.

This wasn’t the first time Gaines had taken on a big kayaking project. He has been paddling for 45 years, and during that time made numerous trips to Nantucket, being particularly fond of the trip from Edgartown to Muskeget Island off the Nantucket coast, which he describes as completely magic. “You sail off over the horizon to this little bit of an island covered with seals,” Gaines said. Although, given all the great white shark activity these days, Gaines says he can’t help thinking about what might be swimming beneath him.

Gaines had also paddled around the Island nonstop on two occasions, once in 2014 as a fundraiser to help save the Gay Head Light. But this trip would be different. He would take his time and explore the nooks and crannies of the Island at his leisure. Each day, depending on the weather and the tides, he would select his route, until he’d covered the entire coastline.

After his successful trip to Pocha Pond on April 6, the next day Gaines would kayak to Eel Pond, and then down to State Beach. Hopscotching around the Island, Gaines would eventually finish his trip on his birthday, July 3. All totaled, he took 26 trips, and traveled 213.7 miles, paddling for 54 hours and 17 minutes.

Gaines looks at the trip in its entirety as an amazing experience, but certain highlights come to his mind. One of his favorite legs was the trip to Squibnocket Pond, partly due to the natural beauty of the pond but also because it was the first summerlike day in the spring.

Gaines also enjoyed his trips up the north side of the Island, a side most people never see. He particularly enjoyed his run from Lake Tashmoo to Menemsha, where he would hug the shoreline in the shadow of the high cliffs and bluffs and meander around the massive glacial boulders.

Gaines got a firsthand look at the changeover of seasons from spring to summer. “At first I saw winter ducks,” Gaines said, “then suddenly they were gone, and the terns and ospreys started showing up, and then I’d see the geese and the goslings and the swans and the cygnets. It was refreshing and motivating to see nature just doing what nature does, no matter what humans are up to. In the beginning of the trip there were no leaves on the trees, and by the end there was full foliage.”

Gaines is from Edgartown, and the trip afforded him the chance to get a closer look at the up-Island ponds. He was impressed that they hadn’t entirely given way to trophy houses; there were still some classic Vineyard camps in evidence, and many of the newer houses “have chosen a more discreet architectural ethic,” Gaines said.

In an email to me, Gaines wrote, “My focus throughout Paddling Through the Pandemic was on the natural environment; I only photographed buildings when they were part of the larger landscape — and made a point of NOT publicizing the domiciles of the rich and famous, nor lamenting ostentation, despite my personal dismay. No Paparazzi Paddling during this Pandemic!”

Gaines concluded his trip on his birthday, July 3, with a beautiful trip over glassy waters from Menemsha to Edgartown. Technically, he had to go back out on August 1 and cover a small area by Fuller Beach in Edgartown he had neglected to shoot, but for the records, Gaines is going with July 3.

Gaine’s Paddling Through the Pandemic did not go unnoticed. Linsey Lee, oral history curator at the Martha’s Vineyard Museum, posted interviews with Gaines on the museum website and Instagram feed, and the Vineyard Conservation Society let people follow Gaine’s adventures on its Almanac page.

Looking back at the whole adventure, Gaines said, “It was a fun way to put a positive spin on everything going on last spring, and I really enjoyed it.” He went out of his way to thank the Land Bank, Sheriff’s Meadow Foundation, The Trustees of Reservations, and the Island towns who provide access to make sure people can get to these beautiful bodies of water.

“Getting out there takes some effort,” Gaines said, “but it’s a way to find some peace and quiet, and a reminder of what the Vineyard used to be — and in many ways still is.”

For a complete list of Dana Gaines’ trips on Relive, visit his



  1. Runners take note. There is joyous life after running. Dana was a prolific and speedy runner for many years. His infectious enthusiasm encouraged many of us to push just a little harder on race day. Sadly life as a runner is finite.

    I’m proud to call Dana a friend. With his eternal optimism and appreciation for all things healthy; he continues to lead the way.

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