With Columbus Day right around the corner, it’s time to start planning for that last annual getaway before the holiday season starts. October is a great time to travel for plenty of reasons: The leaves are starting to change across the country, the weather is starting to become bearable and airfares are starting to drop.

It’s the perfect formula for budget fall travel, as well as a great way to stock up on some good memories before the miserable winter cold sets in. Here are some of our favorite travel picks for 2010.

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If you’ve got yourself a budding thespian (and we do), don’t miss an opportunity to partake in some incredible shows at the Oregon Shakespeare Festival in Ashland, Oregon. Located about six hours north of San Francisco, this tiny hamlet town is reminiscent of an Old World society full of scholars, poets and troubadours. Ashland is also home to several killer coffee shops, great dining options, fantasy and specialty children stores, hiking trails, and parks.

For the last 75 years, OSF has run nine months out of the year and boasts one of the largest repertories in the country. They bring in notable actors and artists from all around who perform in several different theaters, including an outdoor venue. It’s so wonderful to drink mulled wine under the stars while listening to iambic pentameter lilt away. Insanely enough, the kids pick up on it pretty quickly, and the actors are typically very physical with lots of gestures and body language.

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Now is the perfect time to get out and about with the family.  And when I say “out,” I mean “out!”  Why not explore the great outdoors (while sacking out at night someplace roomy and comfy)?  Even the littlest member of your crew will get a kick out of climbing a tiny hill or canoeing down a river.

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What is it about trains that are so fascinating? I’ve seen many a toddler, child, parent and grandparent riveted for hours engrossed in train encyclopedias, hunched over wooden activity tables, and standing along railways with looks of pure bliss upon their faces. Many families invest dollars and hours into the latest and greatest train sets, DVDs and picture books, but nothing quite compares to the real thing! This year why not take a real train adventure with your young ones, and share in the discovery and magic that only an engineering marvel of metal and wheels could captivate across the ages. Read More >