1. Middleburg
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    Amazing home goods stores and antique emporiums, all basically on one idyllic stretch of road. This is sort of a real life Eagleton (i.e. filled with very moneyed horse people). Make sure to hit the Home Farm Store for meats and cheeses, Hotel Salamander for a drink, Market Salamander for lunch and to feel like you're in a Nancy Meyers movie, and my favorite store: The Outpost for unique finds and dreamy textiles. Also, hit up some of the vineyards nearby. It's not Napa, but it's not nothing!
  2. Shenandoah
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    Go in the fall. Get apple cider donuts at the Apple House Deli in Linden and continue to Front Royal to enter the Skyline Drive. $20 gets you into the park (ticket good for a week) where you can hike or just drive down the most scenic, breathtaking routes. Lots of overlooks. Lots of places to eat your donuts. I did this yesterday and it was restorative
  3. Baltimore
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    See an old movie at the Senator. Go to Atomic Books and the American Visionary Art Museum. See @olive, @sally, and John Waters. I only went for a day last year and the city totally charmed me.
  4. Annapolis
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    Nice little city by the bay. Walk the docks and main streets in the summer, visit the Naval Museum, get tacky and drunk on painkillers at Pussers, feel very American. Mess around with some crabs at Cantler's Riverside Inn. Try a slice of the 7-layer caramel cake at Caroline's Cakes (Oprah's a fan). End with dinner at Vin 909.
  5. Mount Vernon
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    Visit ye olde stomping ground of Georgie Washington. There's a cool colonial fair and market in September (where this pic was snapped)
  6. Harpers Ferry
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    It has a cute historic downtown area and and a national park. Go during the fall when it hits peak cozy or summer when you can go drunk river tubing.
    Suggested by @abrunsy