Some places we’ve liked are:

NYC
Philly
Charlottesville
Staunton, VA
Chicago
New Orleans
Vegas for a girls trip, especially when there’s a cool show to go to.

We're in the same boat, OP! We've taken a number of 3 to 5 day trips and have loved them all. We usually go to a city, stay in a Sonder downtown, and sometimes rent bicycles to use as our main transportation method.

We have enjoyed...
Pittsburgh
Richmond
Philly
Kansas City
Toronto
Boston

Some of these were repeat trips for us, but now without kids, it is a much different experience. Don't be afraid to repeat a city and just stay in a different area of town.

Other 'non-city" outdoorsy trips close to home...
Berkeley Springs WV
Fancy B&B by Shenandoah
New River Gorge WV

Anonymous wrote:It would help a lot to post a budget.

And interests

my rule is # of days > = # of hours it takes to get there

pp, I found this helpful and interesting

Anonymous wrote:

Anonymous wrote:Y'all go further for your 3 day weekends than I'm willing to! I was thinking, like, Philly or NY, or Dolly Sods if you're outdoorsy.

+1

my rule is # of days > = # of hours it takes to get there. E.g., NY takes 3 hours, so a trip of at least 3 days/2 nights is appropriate.

Have you explored MD’s Eastern Shore? The Western Shore? The Blue Ridge Mountains? Frederick? Winchester?

My Dad’s rule for day or weekend trips was that we had to be at the location at least twice as long as it took to get there and back.

For driving, this series hits most of the options and gives many ideas.

https://weta.org/watch/shows/get-out-town

[mastodon]

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:Y'all go further for your 3 day weekends than I'm willing to! I was thinking, like, Philly or NY, or Dolly Sods if you're outdoorsy.

+1

my rule is # of days > = # of hours it takes to get there. E.g., NY takes 3 hours, so a trip of at least 3 days/2 nights is appropriate.

Have you explored MD’s Eastern Shore? The Western Shore? The Blue Ridge Mountains? Frederick? Winchester?

Why? That seems like a very strange rule to me.

This is roughly our rule too. But Bahamas would still work. Also Puerto Rico.

But does that mean you don’t go for a quick trip for an event? I love a quick overnight to NYC. Or flying somewhere for a big game, or a concert?

Charlottesville for hiking and wineries.