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Windsor has a lot to offer visitors, from shopping to dinning to all of its festivals in the summer months.
The majority occur during the summer with a plethora of carnivals. Some recommendations include the Fringe Festivals Busker Fest (usually mid-July), the Tecumseh Corn Fest (usually live music from a relevant band on the Saturday night at the end of August), and Summer Fest (end of June). There's plenty more worth mentioning for a variety of tastes...
In Windsor there is some good shopping at Devonshire mall, Tecumseh mall and the surrounding area, the Windsor Crossing outlets, Manning Road, and Walker Road just off the 401. For a more community shopping experience there is Ottawa Street, Erie Street, Ouelette/Downtown, Pilette Village, and Wyandotte off of Chilver. From Windsor you can also quickly cross the border via the Tunnel to Detroit and visit a number of shopping centres most notabley Great Lakes Crossing and Oakland Mall and area.
The highlight of Windsor may be many great locally owned restaurants. It may not be worth mentioning them individually because they can close down in an instant, but some favourites include Bubi's (for the best in garlic food), Rockbottom's, Hurricane's, Dirty Jersey's, and so many more (for great pub food), and so much more.
Windsor's main attraction is the casino Caesar's Windsor which also tends to have good shows. Aside from that there's the beautiful Riverside parks/trail which includes playgrounds, flower and plant arrangements, a bike trail, and a sculpture park, as well as an outdoor festival plaza and stage.
From Windsor you can make a day trip out in Essex County to visit the many wineries, orchards, farms, and beaches. Point Pelee is a famous attraction, but a local secret for families is Colasanti's tropical gardens. Colasanti's has kids rides, bumper cars, mini golf, a great restaurant with famous home made donuts, a fairly impressive zoo/petting zoo that has animal shows that the kids love, and of course a lot of plants to purchase. Leamington in particular is a great place to visit for shopping, the Heinz factory, and the beach/park.