The Story Behind It All

As a couple, one of our favorite things to do has always been exploring beautiful wineries, farms, and breweries. Call it agrotourism, call it weekend wandering — it was our happy place. It was simple: we’d pick a destination, jump in the car, and go.

Sure, we didn’t always find exactly what we were looking for — but we could usually get in, relax, and enjoy the day. That is… until we got a puppy. And then a baby.

As a couple, one of our favorite things to do has always been exploring beautiful wineries, farms, and breweries. Call it agrotourism, call it weekend wandering — it was our happy place. It was simple: we’d pick a destination, jump in the car, and go.

Sure, we didn’t always find exactly what we were looking for — but we could usually get in, relax, and enjoy the day. That is… until we got a puppy. And then a baby.

What Changed

Let’s be honest — adding a puppy already made things more complicated. But once our baby came along, spontaneity went out the window. Unless you had a nanny on call and a doggy daycare reservation, things just didn’t work the same.

I’ll never forget one weekend when we drove out to one of our favorite areas — Delaplane. The views are incredible, and we were excited to share it with our new little family. But at the first stop, we were turned away: “Adults only.” At the next, “No pets allowed.” And the third? Same story.

We drove back home that day — with an untouched picnic basket and two disappointed parents.

The Turning Point

That day lit a spark. We didn’t want to give up on our weekend adventures — we just needed to be smarter about where we went. And so we began researching: which places were truly family-friendly? Which welcomed dogs and strollers? Which had baby changing tables or space for kids to run around?

We started building a list. Then we started scoring each place — not just for dog-friendliness or kid-friendliness, but for things like:

• Stroller access
• Family restrooms & changing tables
• On-site food (and options for picky eaters)
• Shaded outdoor space
• Dog water bowls, leashes, or parks
• Kid activities, live music, or open play areas

From Frustration to a Full System

What began as a simple list turned into a whole system of characteristics. We even found places tailored to couples, special events, or sustainability pioneers — but we’ll save those for another day. This post is about families.

We want to make it easier for other families to get out and enjoy what the DMV area has to offer — without the stress or guesswork.

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Where We’re Headed Next

Here are 3 family-friendly spots we’re planning to visit over the next couple of weekends — all great options if you’re looking to get out and explore with kids (and maybe a pup too):

We’ve got a longer list we’re keeping in our back pocket — if you’d like to see the full line-up, you can sign up for the newsletter here and get it delivered every two weeks.

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Stay Tuned…

We’re just getting started. Coming soon:

• Romantic Getaways for when you do get that sitter
• Green Getaways: venues leading the way on sustainability
• And even a dog-approved trail series for our furry family members 🐾

Thank you for following along — and we hope our guide helps your weekends become easier, smoother, and full of good memories.