Fly from Boston to Windsor, for a taste of rum-running history.
During Prohibition, Windsor was the source of sought after alcohol for thirsty Americans. Now, this illicit history has been distilled into some of the best things to do in Windsor. Historical buildings, museums, and heritage parks make this former rum-running hotspot the toast of Southern Ontario.
Although much has changed since the days of smuggling whisky across the Detroit River, Windsor still knows how to have fun. For the best of the city’s entertainment, you can always bet on a good time at Caesars Windsor. At the WFCU Centre, even more amusement awaits, with concerts, theatrical performances, and hockey all under one multi-purpose roof.
Drink in Windsor’s historic points of interest by touring through the Canadian Club Brand Centre and Walkerville Brewery. After tasting Windsor’s famous whisky and beer at these beverage institutions, you’ll want to raise a glass to Windsor’s rebellious past.
Historic buildings throughout the city shine a light on life in Windsor throughout the years. From the cozy company housing of Olde Walkerville to the grand estate grounds of Willistead Manor, these structures are your window into a bygone Windsor.
Several of the city’s heritage structures come together to celebrate local history in Windsor’s Community Museum. Local artistry is on display in Windsor’s former jail and courthouse, the MacKenzie Hall Cultural Centre. In the Art Gallery of Windsor’s modern building, you’ll find 4,000 of the city’s finest works of art.
30 more pieces of the Windsor’s art collection are scattered along the city’s waterfront, in the Windsor Sculpture Park. Before you go back to Boston, be sure to enjoy the park’s art and the view of the sparkling Detroit River, the former route of Windsor’s rumrunners.
Travel back across the US border during your trip from Boston to Windsor, with a day in downtown Detroit.
To get to Detroit, take the speedy Detroit Windsor Tunnel directly into downtown, or ride the scenic Ambassador Bridge over the Detroit River. Whether you go under or over the water, you won’t have to go far to reach Windsor’s American neighbour.
After admiring Detroit’s distinct skyline from Windsor’s waterfront, get a closer look at these striking structures. From the seven skyscrapers that make up the metallic Renaissance Center, to the 40 storey red brick walls of the 1929 Guardian Building, Detroit features a variety of interesting architectural features.
Several historic buildings act as the main stage for downtown Detroit’s arts scene. Both the Fox Theatre and Fillmore Detroit date back to the 1920s, and still light up the stage with some of Detroit’s top billed acts.
For more modern entertainment, the MGM Grand Detroit hosts live shows, lounges, and nightclubs. Double down on Detroit’s exciting casinos at the Greektown Casino-Hotel, with a variety of gaming and dining options.
Detroit’s entertainment offerings continue in the outdoors at Philip A Hart Plaza. During the summer, this public space hosts the annual Detroit Jazz Festival, which spreads from the Plaza to Campus Martius.
If you miss out on this spectacular concert series, take a shot at Detroit’s sports offerings. At Joe Louis Arena, the Detroit Red Wings take to the ice, while Comerica Park hosts the home runs of the Detroit Tigers. The city’s other big cat team, the Detroit Lions, aim for the touchdown on Ford Field. With so many sporting venues, it’s always game time in Detroit.
Before you return to Windsor, take some time to enjoy downtown Detroit’s surrounding attractions. Whether you head north to Troy, Michigan for amazing shopping, or go south to the beautiful Belle Isle Park, a day in Detroit will be one of the best parts of your trip from Boston.
After your flight from Boston touches down, stretch your legs in the fascinating ecosystems of the Ojibway Prairie Complex.
Started in 1957, with a humble area of 100 acres, the Ojibway Prairie Complex has since grown to six times its original size. Now, with 600 untamed acres to its name, this nature reserve is home to some of Windsor’s most striking scenery.
Five separate parts compose this collection of ecosystems, including the well-loved Ojibway Park. In Ojibway Park, the Nature Centre outlines the animals and plants that live in the park. Along with this educational information, the Centre also hosts wildlife, wildflower, photography and birding programs to enhance your exploration of the outdoors.
Keep an eye out for the park’s animal population as you make your way through the wilds of Ojibway. Ranging from the rare blanding’s turtle, to white-tailed deer, and green herons, the park hosts a colourful collection of creatures. Some of these species aren’t seen anywhere else in Ontario, making Ojibway ecologically unique.
Even if you don’t manage to catch a glimpse of the animals living in Ojibway, you can always count on spotting the area’s plant life. Oak savanna and endangered Ontario tallgrass prairie stand as some of the few remaining swaths of what was once one of the province’s prominent ecosystems. Among these swaying grasses, you’ll find 60 species specific to prairie areas, and over 500 kinds of flowering plants. Occasionally, the park’s vast greenery goes up in smoke, but don’t panic, these prescribed burns are part of the process of preserving prairie ecosystems.
For the best views of Ojibway’s animals and ecosystems, take one of the many trails that trace through the park. If you’re near the Nature Centre, step onto the Windsor Trail. This expansive route through more of the area’s stunning nature will take you to the next outdoor adventure on your trip from Boston.
Fly from Boston Logan International Airport (BOS) to Windsor International Airport (YQG), with a quick connection in Toronto. Boston to Windsor flight time is 2 hours and 55 minutes on average. Connection times vary. The distance from Boston to Windsor is around 1,025 km / 640 mi.
Enjoy complimentary drinks and snacks along the way.