May is known as Black Fly Season in Vermont, a time to avoid due to the abundance of black flies. Columbus Day Weekend is the single busiest weekend in Manchester Village due to foliage seekers and the holiday--another time to avoid.
First, you'll need a car to get there; a two-day rental averages $100-$120 (compare car rental rates with Kayak.com). The ride is three and a half hours north of Manhattan, with much of the trip on the scenic Taconic State Parkway. You cannot consider yourself a true Vermont-bound visitor if you do not stop at the famous diner, now called O's Eatery, 125 miles north of Manhattan in Chatham, New York.
In operation since 1953 and formerly known as Roscoe's Diner, the restaurant makes one wonder if any updates have been made since then. Even if you're not hungry, you'll probably want to stop for your bladder's sake. One look at the menu, and you'll see that Manhattan prices are long gone. For around $5, you can eat a hearty brunch of eggs, home fries, bacon, toast and coffee, which will leave you understanding the rest of the country's disdain for New York City prices.
Return to the Taconic, and just a mile past the diner, be sure to look up at the grassy hills on the right. You will see an enormous sculpture of a head, among other statues, residing on a front lawn. If you look closely, you will see the giant head mouth, "Eighty miles to Manchester." Okay, maybe not, but it's still an oddly wonderful sight.
From the Taconic, take Route 22, the scenic route to Manchester. As you pass through Lebanon, New York, you'll see a multitude of true blue antique stores, well worth a stop. And just one mile out of Lebanon on Route 22, be sure to drive slowly and look for the water pipe located on the right, protruding from a concrete slab with little fanfare. Some days, there are scores of cars waiting to fill up water bottles; other days, there are none. Legend says the water comes from the purest springs in New York. It's quite refreshing, so be sure to fill up a jug.
Continuing on, you will reach the picturesque town of Bennington, home to Bennington College, location of the film Baby Boom and the site of the monolithic Bennington Battle Monument (a mini Washington Monument); you are now just twenty minutes from Manchester Village.
When you arrive in Manchester Village, you will see a perfectly manicured region with exquisite homes, breathtaking mountains and the best factory outlet shopping your eyes will ever see! From Polo to Movado to Nine West to Coach, it's a smorgasbord of true discounted shopping.
But first, check in to your inn. I recommend the dashing Reluctant Panther in the center of Manchester Village. This cozy bed and breakfast is located just steps from the stunning, legendary (and pricey) Equinox Resort and sits at the base of the Green Mountains. As with just about everything in Manchester Village, it is located on Route 7A. Most inns in this area run off-season specials, so check the Web before you go.