For "on the beaten path" in DC, I'd recommend going to the sightseeing around the White House/mall/etc. then having oysters at Old Ebbitt Grill. Then get to the POV on the top of the W Hotel around 8, have one expensive drink, and take in the views. Afterward there are some less expensive bars in the area...The Hamilton sometimes has some free, good music in their Loft area. Cap City Brewing Company isn't too far from there either (closer to Metro Center).
Rose's Luxury in Southeast/Barracks Row is like the hottest restaurant in the world right now, they were named Bon Appetit's Best New Restaurant in the country and all the critics love it. They don't take reservations and waits can be long but you can get there early, put your name in, then head to another bar nearby for a drink, and they'll text you when your table is ready.
The National Arboretum on NY Ave NE is a bit off the beaten path and is gorgeous. Red Hen is a well regarded place nearby and there are bars and restaurants on H Street as well. Red Hen isn't too far from the Metro, but you may need to cab or Uber elsewhere.
The Gallery Place/Chinatown area is pretty vibrant when there's something going on at the Verizon Center. Most of the places around there are chains, but if you have time it can be worth talking a walk around and grabbing a drink. I think Poste Restaurant in the Hotel Monaco out there is putting a fire pit in their courtyard in the next few days, that could be worth a stop.
Depending on where you're staying, don't worry about going out to Arlington or Alexandria, there's plenty to do in town and you won't be able to do it all.
Have fun!
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