Oh Canada!

*** Oswego, NY to Trenon, ON ***

We rose early in Oswego finding ourselves a little antsy for our voyage across Lake Ontario, as it would be another big water crossing. We watched fishing boats leave their docks in the calmest of winds and seas.

Oswego sits on the southeast shore of Lake Ontario and the fetch can build across the lake with a west wind. We went down below to prepare for our long day ahead and a departure time of 7:00 am with our buddy boat Live the Dash. Making our way topside again at 6:30 am, the weather had changed significantly. The leaves were blowing in the strong breeze from the southwest, the water was slapping against our hull, and the boat was dancing in our slip. Many loopers had left earlier and had good jump on us and the ever changing weather. There were just a few stragglers left in the marina with us.

Engines started at 7:04, we made our way into Oswego Harbor and it wasn’t too bad. Oswego Harbor is surrounded by a large stone break wall with a lighthouse at the entrance. We watched Live the Dash hit the open lake by the break wall, we were no longer in a protected Harbor, but now Lake Ontario, our first of the Great Lakes, and she let us know who ruled. Live the Dash lurched to starboard as the southwest winds hit her on her beam. Seemed like this might be a long ride.

The weather forecast, even up to departure time listed waves as 1 foot or less. The waves we were experiencing were 2 – 3’ with a few wild cards thrown in. Mostly against the port side and stern, we were rocking and rolling for the first few hours. Seas changed for the better as we got further into the lake and started up the St. Lawrence River on the northeast corner of Lake Ontario. Still windy but the waves had laid down. Amazingly Tasha and Now or Never fared well, but that wasn’t the case for our buddy boat and others that crossed this day as furniture was rearranged, tables and counter tops cleared, and nauseous crew mates were a plenty.

We ended our 64 mile (6.5 hours) day in Clayton, NY, a charming small town, home of the antique boat museum we visited while docked in Brewerton. We got acquainted with the vibrant downtown, all within walking distance of the marina and the weekend hosted two big events that brought a lot of activity: the Sea Way Splash – Ultimate Air Dog competition and the River Pride Festival.

Clayton, NY

We loved watching the dog jump competition and returned each day to see pups of all pedigrees and talent. Whether it was the pups first event, and they were hesitant to jump 4 feet or they were seasoned jumpers leaping 20+ feet, all were cheered and celebrated. It was a joy for us dog lovers to watch with the beautiful river back drop. The pride festival brought a lot of color to the small town with festivities in multiple locations. We also witnessed our third wedding of the loop with the nuptials taking place along the river in the hotel’s beautiful yard next to the marina.

Clayton, NY

Clayton is located in the Thousand Islands region. The Thousand Islands are a group of more than 1800 islands in the St. Lawrence River, straddling the border of the US and Canada. The islands range in size from over 40 square miles to smaller islands occupied by a single residence or uninhabited outcropping of rocks. To count as one of the Thousand Islands, the land must be within the river channel and have at least one square foot of land above water level year round and support at least two living trees. It’s a breathtaking area that the wealthy used as their playground in the late 1800’s and early 1900’s with grand estates and castles built in the area, one we would tour. A recreational boater’s dreamland with many summer homes, this area is still for the wealthy. There are a few different stories as to the claim that Thousand Island dressing got its’ name from the region.

The Dash crew had connected with looper enthusiasts Todd and Robin via facebook and they graciously offered to take us all on a pontoon ride to tour the area. We were quick to jump on this hospitality from our new friends. The cruise included a three hour incredible back channel tour around the islands, Boldt Castle, and along the border by the international rift where the two countries meet. We were able to see a border patrol station just feet from the mid river island.

Thousand Islands

We had such a good time; they came back a second night and we were again wowed with the area on another cruise! This journey has certainly been enhanced by the people we have met and been able to spend time with. We’re thankful for Todd and Robin who certainly enriched our journey and our Thousand Islands time.

With bad weather on the horizon, we stayed in Clayton a bit longer. We took a day trip on Live the Dash to Boldt Castle so that we could return to the marina that night to wait out the storm. It was a short 12 mile cruise to the grand estate on Heart Island. We were able to dock on the private island alongside the ferry boats bringing many visitors to the castle and boat house just across the river.

Originally a private mansion, George Boldt, embarked on building one of the largest private homes in the US for his wife Louise. The construction halted abruptly with the death of Louise in 1904. Broken hearted, Boldt never returned to Heart Island, passing in 1916 and the castle and stone structures were left exposed for 73 years. In 1977 Heart Island was acquired by the Thousand Islands Bridge Authority for $1. Over 50 million has been spent for restoration and improvements with only 2 floors of the five completed.

Boldt Castle – Heart Island

Today Boldt Castle is open for touring and is accessible by ferry or private boat from the US or Canada as it sits on the border on the St. Lawrence River in the US. It’s hard to fathom the grandness the estate would have been in the early 1900’s as today it’s incredible. We would witness several weddings on Heart Island this day, a popular venue for nuptials, however no reception of any kind can be held on the grounds.

With winds building, we returned to Clayton. We were not prepared for our awakening the following morning and the rough waters in the marina. We felt as if we were riding a bronco in our slip for eight hours. With winds and rain coming from the north, our little marina was not protected. Our boat and crew fared well, though our captain spent time helping other boaters in the marina who were not as fortunate. Lines snapping, hulls being beat against the dock as fenders popped up, it was a crazy blow until it wasn’t. At 1:00 pm everything stopped, like it never blew at all, this was our window to cruise. We would learn later that the winds returned late afternoon and another evening on the dock the boater were rodeo riding too.

We took advantage of the window and were off to Kingston, Ontario, a short 21 miles north through the thousand islands and across the Canadian border. As we crossed the border, we raised our yellow quarantine flag indicating we had not yet checked into Canada. Arriving at Federation Basin, an official customs check in location, we stayed on the boat until the captain called, answered customs questions, and gave our passport and boat identification information. In the olden days, boaters would have checked in in person at the pagoda at the top of the ramp. No two check-ins are ever the same, most like ours focused on firearms (illegal in Canada), amounts of alcohol on board, and reason for entering the country.

Customs and Flags

Once satisfying all questions and information, our captain was given an entry number assigned to our vessel that we will display on Now or Never throughout our time in Canada. We then lowered our yellow quarantine flag and hung our Canadian courtesy flag. We will fly the maple leaf flag aboard Now or Never until we return to the states late summer. Our United States of America flag always and continues to fly from the stern.

Kingston, ON

Kingston will be the largest Canadian town we will visit on our loop, population 165,000. We met up with fellow loopers Leanne and Walt on Journey, (we visited with them the prior day at the Castle) and along with Live the Dash crew would have dinner at the Kingston Brewery celebrating our entry to Canada. Journey would take off heading toward the Trent Severn Waterway the following day, we would stay and check out the city including the Murney Tower and Museum, the Kingston penitentiary, and catch a great concert.

Kingston, NY

Murney Tower is a Martello tower constructed in 1846. It was built in response to a tense dispute over the border between British North America and the United States in the 1840’s. The tower is one of five of Kingston’s fortifications that defended Kingston Harbor, the Naval Dockyard, military supply depot and the southern entrance to the Rideau Canal.

Murney Tower in Kingston, ON

The tower stands surrounded by a dry ditch. Special brickwork was used on the barrack and basement levels. The walls that face the water and the US were constructed 15 feet thick as an attack from the Americans was the most likely form of attack. Cannonballs from enemy shops should have theoretically bounced right off the walls. Other walls were 8 feet thick. The barrack has two internal cannons that would have fired 32-ln cannonballs directed out shuttered windows. They spun on a circle rail that would allow them to shoot from any of the windows. Fourteen Martello towers were built in Canada, only 9 are still standing and four of those are in Kingston. Murney is the only one open to the public. It was a fascinating structure and museum, the captain could have spent all day there.

What does a retired Sheriff and Police Chief do on a boating adventure? We visited the Kingston Penitentiary, a former maximum security penitentiary. It first opened in 1835 and closed its doors in 2013. This large facility sits on the water in Kingston, though there are very few views of the water due to the large retaining wall. The original cell blocks measured 29 inches by 8 feet. The facility housed 500 inmates and every inmate was given an individual cell. The Kingston Pen housed some of Canada’s most notorious criminals over the 178 years it was open.

Kingston State Penitentiary

We shifted gears from war huts and penitentiaries to music. It has been exciting to cruise with the Dash crew (youngsters) leading us to do things we most likely wouldn’t have ventured out to do. It was Emily who found James Taylor performing nearby in Syracuse. With a rental car and two and half hour drive, we were crossing the border back to the states to an amphitheater to see the one and only James Taylor in the rain. There are not too many artists we would slosh through the rain and mud and sit outside (under cover) to see at this stage of our lives, but this was one for the ages. The two and a half hour trip was well worth walking in the rain – how sweet it was!

James Taylor in Syracuse

We had a late night crossing the border to get back to the marina, luckily it was uneventful. Happy to get back to Now or Never by 2:00 am, we slept fast preparing us for an early departure in the morning taking us to Trenton, Ontario some 70 miles west.

Our cruise to Trenton was comfortable, scenic, and long. After a late night with the concert, this crew was tired. It was a cool 68, and we kept the windows closed for the trip, keeping our little bubble warm. We skirted Lake Ontario and weaved in and out of islands. As we left Kingston, we cruised by Murney Tower and the Kingston Penitentiary that we toured the day prior. What views both had, both for strategic purposes. The sun was out and we were excited to get to Trent Port Marina to see our friends Karen and Eric at their homeport and stay through Canada Day.

Our friends on Escapade, Brenda and Wally joined us as they finally caught up with us. They’ve been a few ports behind us since rendezvous two months earlier. They arrived with a new crew member they adopted in Oswego, NY, little Annie.

Annie on Escapade

We had been planning our Port Trent Marina stay for 2.5 years to see visit Karen and Eric on Tropical Horizons whom we first met in Fort Meyers in January of 2022. Over the past couple of years we have crossed paths seven times up and down the east coast. Our visit coincided with the Canada Day celebration and the fanfare of a two day air show, a car show, a Lions Club pancake breakfast, and fireworks.

Canada Day Celebrations – July 1

The incredible hospitality of our friends and harbor hosts included a wine excursion through Prince Edward Island with the crews of Live the Dash and Escapade with Karen and Eric orchestrating the day. We tasted, dined, wined, and stopped at a country store for fresh baked goods. The evening ended with a meal on Live the Dash. 

Prince Edward County Wine Country

Karen as a looper harbor host also took photos of all the looper boats coming and going to the marina, docktails, route briefings, an extensive route book she wrote and shared with all about the Trent Severn Waterway.

Remy’s buddy Tank – always welcomes us

Karen assisted Tasha with route planning for the 240 mile Trent Severn Waterway we were about to embark upon. Their commitment to the looper community is priceless and getting to hang out with them for a week was a pretty special.

This marina is the gateway to the Trent Severn Waterway. This is it. Years in planning. We were finally here. A big part of our dream for so many years.

*  *  *

Our crew just surpassed our three year mark of our journey, it was June of 2021 early morning when we left as a crew of three aboard Now or Never and our home port on the Ohio River in southern Indiana to embark on our great loop journey.

With 9000 miles under our keel, we’ve been abord 713 days cruising to 196 ports. The journey has been so much more than we imagined, and we imagined grand! The beauty, the history, the people, the challenges, America from the water, all have enriched our experience.

Starting as a crew of three (we miss our Remy), we have completed about 2/3 of the loop trek (1/3 with Remy aboard) and anticipate crossing our wake as a crew of two in the fall of 2025. Thank you for following our dream, we appreciate the support from family and friends, as we wouldn’t be able to be on this journey without you. Below is our travel map marking our ports of call. You can find an interactive map on our website, MannAboard.com.

  Cheers!  David, Tasha,  

                  & Remy forever in our hearts!   –   Looped for 1 year and 3357 miles

Follow us on facebook for more frequent updates… Mann Aboard