September: Stock up on items for your home office, since leftover back-to-school supplies will be marked down. Buy up bargain-priced end-of-season items like outdoor grills, lawn furniture, garden ornaments, lawn mowers, beach towels — and don't forget the Speedo. For September travel bargains, Mark says try Paris, Mount Rushmore or Martha's Vineyard.
October: October is usually the best month to buy jeans, as retailers stock up for the back to school rush and by now are discounting the leftovers. If you're looking for something sexier, lingerie (as well as jewelry) often goes on sale in October, as retailers make room for their holiday selection. Adding to a romantic evening: Wines are usually a bargain this month too, as vintners release new supplies to coincide with harvest time promotions. Gardening supplies and tools are often discounted, and remainder lots of perennial plants and other nursery stock can often be had for a small fraction of their original price as nurseries make room for mums, pumpkins and Christmas trees — plus, fall is the best time to plant perennials in many parts of the country. If you're in the market for a new bicycle, October is a good month to shop. And wait until the week just before Halloween to buy your costume — many retailers will have marked them down.
November: Start by stocking up on leftover Halloween candy at a deep discount (most can be frozen to keep it fresh). Many housewares, including cookware and kitchen utensils, are a bargain this month too. Travel in November if you can. Disney (World and Land) and the Bahamas are real bargains then. Cruise lines move their ships around the globe to accommodate winter schedules, sometimes offering dirt-cheap "repositioning cruises" to passengers rather than moving the ships empty. (FYI, they do the same thing — only in reverse — every April.) November is also the best time to buy toys for the grandkids. Don't buy just for the year-end holidays, but stock up for their next birthdays as well. Stock up on turkeys, hams and other holiday meats for the freezer. Look for special "loss leader" sale prices on these items at most grocery stores during the Thanksgiving and Christmas seasons that are likely to be the lowest prices of the year.
Jeff Yeager is the author of The Ultimate Cheapskate's Road Map to True Riches and The Cheapskate Next Door. His website is www.UltimateCheapskate.com and you can friend him on Facebook at JeffYeagerUltimateCheapskate or follow him on Twitter.
Updated Fall 2012
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