Senior Member
Join Date: Aug 2009
Location: Minneapolis
Posts: 5,789
Bikes: 2022 Salsa Beargrease Carbon Deore 11, 2020 Salsa Warbird GRX 600, 2020 Canyon Ultimate CF SLX disc 9.0 Di2, 2020 Catrike Eola, 2016 Masi cxgr, 2011, Felt F3 Ltd, 2010 Trek 2.1, 2009 KHS Flite 220
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Yes to a trainer.
As above, riding outside in the winter IS an option in the midwest. If you have the right gear, some of the most glorious rides you'll ever take can be on a crisp snowy winter morning.
But before either, what you should be thinking about is how far into the fall you will be extending your outdoor riding season. Outdoor riding as the leaves turn is not to be missed, but you can't do it in summer kit. Gloves, hat, socks are the first things to be thinking about. Possibly also different tires, depending on what you are riding. Having the right gear for the fall conditions is key, and you won't get them all at once. It's an accumulation and learning process.