Small towns in the Northeast are charming enough already, but when they've dedicated an entire festival to harvesting fall's most popular fruit, why miss this special window of opportunity?  Neighboring historic Gettysburg in Adams County, Pennsylvania, the National Apple Harvest Festival is the perfect fall day trip from Philadelphia, Pittsburg, Baltimore, or D.C.  Held the first two weekends of October, expect live entertainment, hay rides, pie baking contests, the tastiest apple cider, and so much more.  I recommend making The Dupont Circle Hotel in D.C. your home base so you can experience peak autumn in the U.S. capital.  Enjoy sophisticated rooms boasting pops of color, and stay on the ninth floor for floor-to-ceiling windows and private balconies offering bird’s-eye views of the cityscape.
 
Private Perks: $100 dining credit, complimentary daily breakfast, early check-in/late check-out, complimentary upgrade, and more.