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I don't have any tips specific to DC, but I will highly recommend a carrier. Strollers are hard to maneuver in public transit and sometimes the sidewalk just sucks, but a carrier is far easier and they can nap in it!

In Old Town, I loved Majestic Cafe for a special dinner. Food is fantastic but I was so impressed with how they handled the kids. They have a kid’s menu with real food and kid-sized flatware and the staff are just very accommodating to families. Are you staying on King St? Definitely stop in Hooray for Books if you’re near the metro. My kiddos also enjoyed riding the trolley although it’s a bit of a pain with a stroller. Depending on where in Old Town you’re staying, I can give some playground recommendations as well.

My in-laws live in DC but I'm more familiar w the MD suburbs and NW. There's a great indoor playspace in Rockville called Badlands but you'd need a car; also in Friendship Heights one called Busybees, with a Potomac Pizza next door--makes for a perfect kid-morning! But less exciting for parents--that area is basically a large shopping mall. I adore the American History Museum but lo1 was a little bored, except that there's a great small area with play materials. There are a couple fast food chains that have high quality food that I love in DC--Cava is like chipotle but with mediterranean/middle eastern food, and Taylor Gourmet has the best sandwiches. Both great for a quick bite with kiddos that actually is super yummy

Old Town itself is very walkable and has lots of cute shops to browse. Some are easier to navigate a stroller in than others, but in general we’ve found it’s a pretty easy place to explore with a kid. For a practical tip there, some of the sidewalks are brick and kind of uneven - we’ve had best luck with a sturdier stroller.

In DC, we’ve enjoyed most of the Smithsonian museums and I love that they’re free. Some of our other favorite museums are the Newseum and the National Building Museum. There’s some fun stuff for toddlers and older kids at the National Building Museum - my three year old has fun, but I don’t think my 11 month old cares much one way or another.

Yeah, in Old Town there are a lot of brick and cobblestone surfaces, so a lightweight stroller may not be great for walking. My kids aren't keen on being worn, so if they get fed up, we usually just let them sit on our shoulders and they seem pretty content with that.

There is a Soft Play Room at the regional park center for young toddlers:

https://www.alexandriava.gov/recreation/info/default.aspx?id=12352

Please check the events calendars for the Smithsonians and the US Botanical Gardens - they have a lot of free workshops and classes geared for kids. I know my SAHM friends in DC take their kids to the Botanical Gardens all the time because there's lots to look at.

I may be partial because I used to live there, but I love the Del Ray neighborhood. Its not Metro accessible, but should be an easy Uber or cab ride from Alexandria. Its a cute little walkable neighborhood with lots of shops and things to look at and eat.