Washington's Hamptons - Almost

I have had several people ask me about where Washingtonians with style go to get away from the “beltway thing” for a few days. Though most people don’t know it, Washington is actually blessed with good geography and the interesting unique places that go along with options that range from rolling horse country to seaside waterman towns.

For the land loving horsey set, Middleburg, Virgina, is the place to be. Chock full of high-end antique stores and boutiques carrying life’s little necessities, including hacking jackets, Barbour field coats, and handmade paddock boots. This is where you go to see the steeple chases and relax at any number of luxurious bed and breakfasts.

All that said, when I think of a classic Washingtonian weekend getaway, I think of Maryland’s Eastern Shore. It’s a totally separate place, a world distinct from official Washington. Once you cross over the Chesapeake Bay Bridge, a 4 1/2 mile ribbon of steel, you enter a more relaxed and rural universe.

Though less than two hours away from the nation’s capital, the town Easton feels like you have stepped back in time to place where no one really cares what you do or who you know. The stately brick buildings, tree lined streets and elegant homes of the town’s center tempt you to drop everything and just stay. Every spring, Easton hosts a plein air art festival that has hundreds of artists setting up their easels across the town. You’d think you were on Martha’s Vineyard. There is some great shopping in Easton as well. Stop by the House of Harrison to pick up a pair of Bill’s Khakis for the weekend.

Take a turn down Route 33 and you will come to the wonderful town of Saint Michaels, which has been called Washington’s Hamptons by the New York Times. This preppy little town, set alongside the Miles River as it wends its way to the Chesapeake Bay, traces its history back to the early 1700s. Notable current residents, at least those with large vacations mansions, include Vice President Dick Cheney and former Defense Secretary Donald Rumsfeld. Talbott Street, its main thoroughfare, is lined with wonderful shops and interesting restaurants, including the award winning Saint Michaels Winery.

At the edge of town is the Inn At Perry Cabin. This Orient Express owned hotel is exceptionally luxurious in a very laid back fashion, but you’ll still want to get a shoe shine before you show up. Back up the street in the center of town is the Five Gables Inn and Spa, itself a renowned destination. Next April, the growing Saint Michaels Food and Wine Festival will again attract chefs and foodies from around the world. Make sure to put this event on your social calendar.

Think you might want to stick around? If you’re looking to match your wardrobe to your newly discovered life, stop by Sailor and pick up some new Vineyard Vines duds, or head over to Keepers Orvis to stock up for your private fly casting lesson. Need to outfit the new vacation house in an appropriate old money-cum-seaside cottage look? Coco & Company has been featured in Vogue magazine and even helped furnish an HGTV dream home. That’s pretty Hampton-y.