“To travel is to live,” is a famous quote from Hans Christian Andersen. It’s also a tattoo I got in Barcelona when I was 27, because what else says millennial more than an inspirational quote tattoo and a “YOLO” mentality?
Before kids, I traveled constantly. New cities, work trips, spontaneous weekends with friends. There was something thrilling about landing somewhere unfamiliar with nothing but a carry-on bag and absolutely unrealistic expectations about how much sleep I’d function on.
Now? We travel with kids. And if you know, you know.
Traveling with children is basically a three-ring circus disguised as a vacation. Someone always has to use the bathroom at the wrong moment (special shoutout to the car potty!), and somehow you end up packing enough supplies to survive a minor natural disaster.
As much as I’d still love to hop on a plane to somewhere new, I’ve realized that air travel at this stage of life comes with a level of planning my brain simply no longer has the bandwidth for. More often than not, I default to somewhere in the Caribbean because “all-inclusive” feels less like a luxury and more like a survival strategy.
Lately, though, I’ve really been leaning into road trips. Driving takes away the airport chaos, and honestly, I love the spontaneity of discovering little towns, roadside diners, random antique shops, and weird attractions you’d never plan for. Even with the extra snack stops and emergency playground breaks, road trips just feel easier right now.
So here are a few of our favorite family trips from the last few years.
1. The Catskills, NY
There’s something magical about the Catskills. I still remember the first time I visited in my early twenties. As someone from Brooklyn whose family rarely ventured “upstate,” it honestly felt like discovering another planet.
The second I’m surrounded by mountains, this overwhelming calm comes over me. And the best part? It’s actually a very manageable drive from Westchester, usually around two hours, which means we can often make it with only one rest stop and approximately 47 snack requests.
One of my favorite places to stay is Phoenicia. It’s a small, walkable town with cute restaurants, little shops, and plenty of cozy Airbnbs. Just a few minutes away is Woodstock, which is equally charming and surprisingly kid-friendly.
Some favorites:
- Exploring local art galleries
- Candlestock, the local candle shop (which somehow fascinates children for much longer than expected)
- Browsing vintage stores
- Easy hiking trails nearby
Another favorite summer stop is Belleayre Beach at Pine Hill Lake. It’s one of those perfect family spots that somehow checks every box: a sandy beach, swimming area, paddleboat rentals, picnic tables, and beautiful mountain views everywhere you look. We spent hours there, and it felt like the kind of old-school summer day you want your kids to remember forever.
The food is incredible. We frequent Bread Alone for coffee and can usually find a flea market down the road. For dinner, SILVIA is incredible and by far my favorite! It’s definitely more of a date-night spot if grandparents are in town and you’re feeling ambitious.
If your kids are older and adventurous, there are nearby tubing, kayaking, and rafting options. You can also take the scenic train rides in the area, which younger kids usually love.
2. Ludlow, VT
Vermont is a bit more of a commitment drive-wise, but it’s so worth it.
Okemo Mountain Resort is obviously known for skiing in the winter, but summer in Vermont is wildly underrated for families. Okemo Mountain transforms into an adventure park with:
- A mountain coaster
- Zip lines
- Mini golf
- Scenic lifts
- Mountain biking
It’s especially great for bigger kids with lots of energy to burn (ages 7 & up).
The town itself is adorable, with restaurants like The Hatchery and Off the Rails, plus a crystal shop that completely blew my son’s mind. If you have a kid who loves rocks, prepare to leave with approximately 14 pounds of gemstones.
There are gift and coffee shops in town, live music, and a Sunday farmers market that makes you briefly consider moving to Vermont and becoming the kind of person who makes their own jam.
One of the highlights of the trip was Camp Plymouth State Park, located on Echo Lake. It has:
- A sandy beach
- Swimming
- Kayak, canoe, and paddleboard rentals
- A playground
- Picnic areas
- Volleyball courts
We spent an entire day there, and it was so peaceful.
3. Pittsburgh, PA
If you’re open to a bigger adventure, don’t let the drive to Pittsburgh scare you off. Google Maps says it’s about seven hours, but with kids, I’d mentally prepare for closer to nine. We made several stops along the way, including lunch in Lewisburg, which ended up being one of those unexpectedly charming little towns you immediately start Googling real estate prices in.
Home to Bucknell University, the downtown area was quiet when we visited for summer break, and filled with boutiques, bookstores, art shops, and restaurants. Ironically, the shop we went to for lunch was owned by a woman from the same Brooklyn neighborhood where I grew up. Small world, they say!
Pittsburgh itself completely surprised me. Everyone was friendly, the city was easy to navigate, and it had a laid-back, underrated charm. One thing I did notice: everything closes early. By 8 p.m., the city collectively seems to decide it’s bedtime, so you should definitely plan with that information in mind.
A few family favorites:
- The Terminal in the Strip District for shops, food, and live music
- Pittsburgh Zoo & Aquarium is absolutely worth a full day
- Frick Park for trails and playgrounds
- Exploring Regent Square for coffee shops and local restaurants
