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© 2020 by Digital Era Media Inc. 

The Great Loop- North America’s Biggest Boating Adventure with Kurt & Leanne Penfold

Updated: Mar 26

By: Scott Way

The Gold Burgee for 1st completion of The Great Loop (Photo courtesy Kurt & Leanne Penfold)

The Great Loop is everything its name implies, a circular journey through the eastern half of North America that takes boaters on an adventure befitting the ‘Great’ in its name. The route involves navigating the Great Lakes, making passage through the Illinois and Mississippi rivers to the Gulf of Mexico, along the eastern seaboard of the United States, and finally back to the Great Lakes waterway. You can, of course, start at any point along the way, or run it in reverse, but no matter where it begins, crossing your wake upon your return solidifies your success at one of boating’s best adventures.


For lifelong boaters Kurt and Leanne Penfold of Elmira, Ontario, their adventure was 12 years in the making and includes everything that makes a great story: tragedies to endure, obstacles to overcome, sacrifices to make, risks to calculate, and luck to catch. Succeeding in doing ‘The Loop’ twice consecutively (once 2017/18 and again in 2018/19) the Penfolds have experienced just about everything a boater can imagine while travelling over 19,000 kilometres by water. Kurt was born in Perth, Ontario, a quaint town on the Tay River not far from Lake Ontario. His youth was spent boating on the nearby Rideau Canal, working seven summers as a canal man throughout high school and university. He met Leanne at Queen’s University in nearby Kingston and their love for the water, and one another, has kept them together as captain and first mate since 1978.They raised their family in the small town of Elmira; a rural hamlet in southern Ontario where Mennonites in horse drawn buggies gallop down main street and only three stoplights signify the town’s beginning, middle, and end. It’s a world far removed from a harbour town. But Elmira, like much of Ontario, has a sneaky proximity to the Great Lakes in almost every direction, creating a reachable passageway to waterways far beyond Elmira’s endless corn fields. In just a couple hours boaters with an eye for open water can tap into one of the Great Loop’s many veins and commence a circuitous journey through the heart of North America. The Penfolds, like so many boaters, had their eyes on the Great Loop long before a serendipitous mix of timing and ambition kickstarted their journey. Their experience on Ontario’s North Channel ignited a passion for something bigger; a dream of completing ‘the Loop’became entrenched at the top of their bucket list.If you’re a boater, or even just a landlocked globetrotter with wanderlust, The Great Loop can captivate any adventurer’s imagination.


Festivus (Photo courtesy Kurt & Leanne Penfold)

Life has a habit of surprising us with its unpredictability, changing our worlds on a whim with unforeseen trials and tribulations. For the Penfolds, a life altering family accident in 2001 did just that, making life’s fragility clear and, in the process,serving as proof that traffic jams and conference calls don't satisfy our hopes and dreams. As an executive with an Elmira-based engineering firm Kurt began working remotely occasionally, affording him and Leanne more time with their two sons Chris and Matt (both of whom are also engineers), daughter-in-law Lauren (a school teacher), and granddaughter Avery. Time with family brought healing, and life began to move forward again by 2005. That period ingrained a newfound (and hard-earned) desire in Kurt and Leanne to build new memories, a desire that Kurt actualized by forging plans for a Great Loop adventure. But even with the dream set, it would be another 12 years before they pulled away from shore, those years spent as they often are; working, raising a family, and pushing the departure date further back with the belief that you’ll have more time later.


Navigating 'The Loop' usually takes between 10-14 months depending on the scale and timing, but before untying the last cleat there’s a wealth of knowledge to absorb. For the Penfolds, preparation required finding the time to educate themselves about the journey and lifestyle, a laborious but enjoyable task all its own. With a growing family at home and an equally fledgling desire to partake in the trip of a lifetime, by 2017 it was clear that a departure date was no longer hopeful, it was probable. Planning to undertake the Great Loop often takes longer than the trip itself, and with a departure date looming the Penfolds became increasingly aware of what the trip would require:


Leanne: “Kurt picked this dream in 2005 and we started researching at that time, which included joining the America’s Great Loop Cruisers Association (AGLCA) and reading their information and studying the charts and geography for the journey. We had been navigating by boat up the east coast of Georgian Bay and north of Manitoulin Island since 2001 and in the process learned about navigation, weather and associated sea state, currents, seiche, anchoring, boat operation and systems during our vacation time every year. We attended one Trawler Fest in Florida in 2015 and took the courses offered there. Two months prior to moving on board in June 2017 we attended a four day AGLCA Rendezvous in New Bern, North Carolina, and the seminars and discussions with people who were navigating and living this lifestyle were very helpful. They covered stuff that we didn’t know, like where to obtain help or find local information wherever we were,tides, tidal currents, navigating the Bahamas and the Gulf of Mexico, as well as navigating the Intracoastal Waterway (ICW) and the waterways from Chicago to the Gulf of Mexico.”


Life often keeps a boat moored longer than we’d like for all the usual reasons; boardroom meetings, Thanksgiving dinners, and the notion that ‘next year will be the year.’ But with a date in June circled on the calendar, the trip was quickly becoming a reality. The thrill of their impending departure brought a mix of emotions, something Kurt and Leanne both felt in their own way:


Leanne: “Kurt has many years of boating experience. His family lived on the Rideau Waterway and they always had a boat, plus he worked seven summers on the Rideau Canal as a canal man through high school and university, so I wasn’t concerned about knowledge on the water. For me, the concern was the weather.”

Kurt- “Before starting I stressed about the stuff I hadn’t experienced yet. Fast currents in the interior U.S, the commercial traffic especially in the big rivers south of Chicago, the wicket dams and large locks, open ocean and Gulf passages, the large tidal swings and associated currents and shoaling up the Intracoastal Waterway. All that stuff I read about and attended seminars on before we left and, as it turned out was all manageable with no huge surprises. We planned based on weather and that was not a concern prior to initial departure, but there were surprises there, like good forecasts but bad actual weather, where in one case there was no Plan B. That was scary.”


Their departure was a euphoric moment after 12 years of waiting. Looking back on that moment, Leanne confessed that the “the biggest emotional high was that we had actually finally departed on this big adventure. After so many years of thinking about and planning it, we were finally on our way.” For his part, Kurt was equal in his assessment: “it was a big surprise to our friends and family that the dream started.” Their dream was underway.


Shotgun Bay, North Channel Lake Huron (Photo courtesy Kurt & Leanne Penfold)

Travelling aboard their 44 foot Regal Express Cruiser Festivus, the Penfolds departed the Port of Orillia on Lake Simcoe in central Ontario in late June 2017,heading west for the United States via the Great Lakes. At its most basic, the route they traveled is as follows:


They journeyed west through the North Channel before checking into the United States in Sault Ste. Marie. They ran south through Lake Michigan until entering the Illinois River system through Chicago, eventually linking up with the almighty Mississippi River. Then they headed up the Ohio River and down the Kentucky Lakes and Tom Bigbee Waterway to carry them into the Gulf of Mexico at Mobile, Alabama. Travelling the big waters of the Gulf they followed the Florida Panhandle to Carabelle, then crossed the corner of the Gulf of Mexico to Tarpon Springs and turned south down to the Intracoastal Waterway to Ft. Myers. Next they crossed Lake Okeechobee to Stuart and then south to North Palm Beach on the Atlantic side. From there they headed east across the Gulf Stream in the Atlantic to the Abaco in the Bahamas for a 6 week tropical sabbatical before beginning their return to the Florida coast and starting northern ascent. They headed up the Eastern Seaboard with stops in Charleston, South Carolina and Chesapeake Bay via the Dismal Swamp to Norfolk, Virginia among others. They continued running north to New York City and then traveled the Hudson River to Troy, NY. They followed Troy north through Lake Champlain to the St. Lawrence River, then west to Montreal, north up the Ottawa River to the nation’s capital, and then followed the Rideau Canal system to Kingston. From Kingston they traveled west and entered the Trent-Severn Waterway, crossing their wake at Port of Orillia in July 2018, and again in July 2019.


Day to day travel by yacht brings about the usual concerns like weather and water levels, but to ensure steady progress Kurt and Leanne began each day began with a dizzying checklist. The list involved analyzing the weather report, tidal report, swell and wave forecasts, wind expectations, and more localized issues like lock schedules, marina slips, and resupply options. But no amount of studying can prepare you for the inevitable surprises of life at sea. Few had greater impact on their journey than their crossing of the Gulf Stream from the Bahamas back to coastal Florida in March 2019, where a clear weather report belied dangerous waters ahead:


Leanne: “Two times in two years the weather reports were incorrect to the extent it caused us trepidation. The first was on our second Loop trip on our return from the Bahamas. The first 2/3 of the 180 mile trip from Green Turtle Cay in the Abaco was awesome. Once we entered the Gulf Stream from the Abaco continuing on to the Lake Worth Inlet in Florida the seas became rougher and travelling was very uncomfortable. If Kurt turned the boat around we would have breached it. So we kept on towards Florida, reducing our speed to make things as comfortable as possible – but it wasn’t great….water came over the bow regularly and we also had a beam sea meaning that the boat was rocking side to side as well. It felt like being in a washing machine. That lasted for about 60 miles. Five miles from the inlet, it finally calmed down.”


A moment of calm in the Abaco before crossing of the Gulf Stream (Photo courtesy Leanne & Kurt Penfold)

Having escaped the Gulf Stream and landing safely in sunny Florida, the Penfolds had passed the halfway point. With the Eastern seaboard now always to port, the remaining section would take them north past Georgia, the Carolinas, the southern tip of Virginia, and into Chesapeake Bay. But it was here they endured their second daunting experience:


Leanne: “After leaving Norfolk, Virginia on Chesapeake Bay again in 2019… after about 10 miles, visibility became very poor and a nasty, on the nose, sea started. The larger waves that were coming over the bow pushed the anchor and chain up and dislodged the chain from its locking device near the windlass and our anchor slipped down about 2 feet and was occasionally banging on our fibreglass bow. Thankfully the windlass held the anchor suspended in that location because there was no safe way to fix the problem in the sea state we were in. We headed to the nearest port 8 miles away, Port Charles on the southeast shore of the Chesapeake. It was nasty all the way into the harbour. If the weather reports in both cases had predicted that weather, we would have stayed put until it improved and the seas calmed. Captain Kurt kept his cool and did a wonderful job in both instances.”


After repairs in Port Charles and a chance to recollect themselves (and the contents of the cabin), they carried on northbound towards New York City. Not to say that the trip wasn’t without some other surprises not caused by wind or waves. Even with years of preparation behind them, including attending a seminar run by the Loopers Association (AGLCA) who organize resources and help boaters plan for their trips, they were nearly scuttled early on when American bureaucracy left them docked:


Kurt: “The number one surprise was finding out in year one (2017), when we were well south of Chicago going down the Illinois River and near entering the Mississippi, that we required a cruising license to proceed. It was illegal to be living in our boat inside the United States and the only way to obtain a cruising license was from outside the USA through an application and waiting period. We found out about it from another live aboard traveler from Canada and confirmed it with a boating couple who we encountered who came across the Atlantic from Norway to do the Loop. We called US Customs immediately and were required to interview with them when we reached Florida, and we had to call into Customs every time we made a passage en route to Florida. We interviewed with a nice senior officer once we got there and he awarded us the cruising license. He had the authority to break the rules, thankfully.”


Like the waves and the tides,all great adventures include highs and lows. What the Great Loop asks of boaters is to put aside a conventional sense of routine and live by what’s off the bow for long stretches of time. Being away from regular life inevitably becomes painful; the demands of the trip make it clear that to succeed sometimes means being away when you’d rather be home:


Leanne: “For me it was Thanksgiving weekend of 2017 a few months after we departed. Our sons, daughter-in-law and granddaughter were spending Thanksgiving with Kurt’s sisters and family and we weren’t with them for the first time in many years. I had a good cry, we Facetimed, and I never had the same sad feeling again. I still missed everyone, but it was OK.”


Kurt: “Also in 2017 one of our good friends back home passed away of a heart attack and that was a shock to everyone. We were 200 miles or so north of Mobile, Alabama, not close to civilization. Over the 26 months we were gone there were three others back home who left this earth, including a lifelong friend, my first friend, and not being there as we would have been if we were living at home were low points for me.”


At times the challenge of spending 26 months abroad loomed front and center, but despite the personal challenges the highlights made it clear the juice was worth the squeeze. The Penfolds planned their schedule around weather as opposed to deadlines, giving them ample time to explore some of America’s best sights. Too many to list, they gave their highlights below:


1) Mackinac Island, Michigan- “Just beautiful. We stayed on the mainland side with the boat at the State Marina, which is very protected, and took the ferry over to the Island. Beware the Island Marina is a bit exposed to a south wind and there’s lots of waves from ferries.”


2) Canadian North Channel- “Of course. Our home base. Many great places to anchor out in sheltered locations and explore with the dinghy.”


3) Chicago Dusable Marina– You can walk from here to see the sights, take tours shop and dine – Chicago was awesome.”


4) The Bahamas – “We stayed on Green Turtle Cay in the Abaco and traveled to Marsh Harbour, Treasure Cay, Little Harbor, and Hopetown – beautiful turquoise waters, sand, sun, flowers, friendly people and other places in the Abaco both years.”


5) New York City and Liberty Landing Marina– “You can visit the Statue of Liberty, take trips into NYC, explore Times Square, take a tour of Central Park. We were moved by the tour of the Ground Zero Memorial. It was one thing to remember September 11th, but to actually go there brought home to us the emotional and life impact it had on so many people.”


6) Charleston, S.C. –“There’s so much Civil War history to explore. It’s endlessly interesting”


7) Annapolis, MD – “We toured the Naval Academy, took the commuter bus to Washington to see Smithsonian and the Capital. It’s got a quaint city centre with great shops.”


8) “So many more places…..Lake Champlain, Beaufort North Carolina, Tarpon Springs Florida, the small towns along the river and canal systems from Chicago to Mobile Alabama, Chambly Canal in Quebec, the city of Montreal, the locks in Ottawa, the Rideau Canal, and our second home of Kingston, Ontario.”


Exploring Green Turtle Cay, Bahamas in the dinghy (Photo courtesy Leanne & Kurt Penfold)

It seems only reasonable that spending 26 months in an enclosed space presents unique challenges. Working in unison in what amounts to a studio apartment tests the resolve of any partnership. There is rarely alone time, and the demands of each day mean both parties never truly get a day off. Delightfully heart-warming, Leanne and Kurt found strength in their unity and learned that home wasn’t necessarily back in Elmira:


Leanne: “Living with my husband in a house is one thing,and living in such a small space could have been disaster, but it wasn’t. Many of the items we have that were left stored in bins and boxes at home was just stuff I didn’t need to make me happy. I learned I could be content with less. A “home” – that comfortable place where you want to be when you’re tired or sick or just to escape the busyness of life doesn’t have to be a house. It is where you walk in the door, hang your hat at the end of the day and say “I am glad to be home” - where the person that you’ve shared life experiences with is,and that you want to be with to share the adventures yet to come. Having spent the last few months living close to our boys, daughter-in-law and granddaughter, I want to live relatively close to them where visits aren’t just about Christmas or Thanksgiving. I learned that friends are very important; particularly long standing ones, who know me well and are always there for me. I sure missed my girlfriends: lunches out, coffee, retail therapy, talking while walking and just venting. I did make one new special friend on our trip with whom I could share all those things.”


As the trip progressed Kurt and Leanne also found solace in the friendships they forged with other Loopers along the way. Fellow boaters proved welcoming throughout the journey, offering support with each passing mile. Socializing became a customary part of shore time and new friendships were forged over docktails at various marinas throughout Canada and the U.S:


Leanne: “We met so many other Loopers on the trip. We all started at a different place, for the most part, so some had more experience and some less when we crossed paths. We would quite often leap frog with other boats. Docktails were held quite often; when the folks from one boat would say “let’s get together around 5 for docktails.” This could be on their boat, our boat, or at the marina if space allowed. We would each bring our own beverages and a snack to share. The conversations centred around our travels for the most part, and sharing experiences and knowledge with each other was invaluable.”


After crossing their wake the second time on July 14th, 2019 Kurt and Leanne switched out their weathered AGLCA Gold burgee (for 1st completion) for a Platinum one signifying their 2nd completion of the fabled Loop. So what does the future hold for a pair of seasoned boaters who’ve seen so much of North America’s waterways? A trip to their old stomping grounds in the North Channel, of course:


Kurt: “We’ll move on board again this May and live aboard traveling up the coast of Georgian Bay, across the top of Manitoulin Island and half way down Lake Michigan, then back to Midland Ontario. We’ll explore places we haven’t explored before, and we may embark on a third loop starting May 2021.”


Replacing Gold with Platinum- Completing the Second Loop, Port of Orillia, July 2019

After travelling over 19,000 kilometres, through 15 U.S states and 2 provinces, and amassing a lifetime of memories packed into 26 months, the Penfolds have experienced some of the best, and endured some of the worst, of North America’s waterways. From withstanding tropical storms and overcoming loose anchors in the Atlantic Ocean, to enjoying perfect sunsets and docktails overlooking beautiful Georgian Bay, they have earned the right to call themselves Loopers. With an ambitious 2021 ahead and a third Loop trip penciled in, both the Penfolds and the Festivus will no doubt be waiting restlessly in Midland harbour for their next grand adventure.


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