CapNY History Day Trip: Visiting Olana with Kids

I’ve been visiting the Catskills since I was a kid, and the best part of the drive was always looking up at Olana from the Rip Van Winkle Bridge over the Hudson River. The views from its hilltop perch are even more breathtaking than those from below.

It seemed like a dreamy place to explore with my family!

Historic Olana

Historic Olana

Olana State Historic Site is a 4-season destination, so visiting Olana with kids is always an option!

Olana is a towering castle-like villa atop a leafy hill overlooking the Hudson River. Among the most iconic views in the Hudson Valley, Olana was home to painter Frederic Church in the 1800s.

Even in the weird times of travel restrictions, it’s the perfect place for a day trip. Due to COVID concerns, you can’t go inside the Olana State Historic Site at the moment (but check their website for updates). The villa is still beautiful from the outside. And the real magic of the place — especially for kids and kids at heart — is in the 250 acres surrounding this historic home.

Olana Family Tours

Child looking at an overview of Olana

Carolyn Keogh is the Olana Partnership’s Director of Education and Public Programs. “While our outdoor tours are open to all ages, this year we began a new tour format for families, our Family Explorer Tours. These provide more interactive opportunities for families to learn together by participating in activities like drawing and other kid-friendly conversation prompts.”

When you’re visiting Olana with kids, my advice is to book an outdoor family tour. Or if your kids are too little for that, you can explore the vast, beautiful grounds on your own. Explore the trails and soak up the greenery that inspired the artists who walked these hills before us.

If you want to take a guided tour, you’ll want to book in advance, as they do fill up. Electric Carriage Tours are available, for anyone who’d prefer to be driven around the 250 acres of landscape design. At present these 60-minute tours cost $150 are limited to up to 4 passengers from the same household.

Outdoors at Olana

Outdoors at Olana

Olana is a wonderful 4-season destination, welcoming snowshoeing and cross-country skiing as well as walking in the wintertime. In the spring, the Mingled Garden bursts into pastel-colored bloom. Then the show of flowers turns into deeper reds and oranges, to attract hummingbirds in the height of summer. In the autumn, it’s common to spot a painter behind an easel, capturing the awe-inspiring fall foliage on display. Small children don’t always have the deepest appreciation for scenic lookouts. My kids love matching up Olana’s view of the Catskills with the mountains pictured and labeled on the park map.

Where to Eat With Kids in Hudson

Casa latina Pupusas Y Mas

After visiting Olana with kids you’ll want kid friendly dining options. The village of Hudson is located just 10 minutes north of Olana. There, Casa Latina Pupusas Y Mas, a mom-and-pop counter-service spot serving traditional fare from El Salvador and Mexico. It’s our family favorite. Away from the hustle and bustle of Warren Street, they’ve got ample parking, umbrella tables, and crave-worthy pupusas – corn masa flatbreads that are stuffed with tasty fillings like cheese, beans, or chicharron (fried pork belly). They also serve nachos, tacos, quesadillas, a kid’s menu, and a must-try juice of the day. My daughter lives for their watermelon agua fresca.

Grazin Diner

If your crew is more in the mood for burgers, hot dogs, grilled cheese, and fries, Grazin’ Diner promises a hearty meal that you can feel good about. All of their meat is sourced from their nearby farm, all their produce is organic, and almost every ingredient they serve is local. For instance, on their incredibly juicy Unburdened Burger with baby Swiss, the bourbon used to sauté their mushroom and make their steak sauce is sourced from Ghent’s Unburdened Distillery. And the sweetest way to end a day after a long stroll around Olana’s carriage roads is a Grazin’ milkshake paired with their house-made brownies, cookies, and pies.

Connect With Olana

Written by: Kara Zuaro, Brooklyn Doublewide

Exploring the less traveled (and less expensive!) Catskills, in and around Greene County. Farms, drive-in movies, kids, food, beer, shopping, home design, and real estate.